Synthesis and Properties of N-, O-, and S-Phospho Derivatives of Amino Acids, Peptides, and Protein

References

• Cohen P. Recently Discovered Systems of Enzyme Regulation by Reversible Phosphorylation. Elsevier/North Holland, New York 1980
   Google Scholar
• Rosen O. M., Krebs E. G. Protein Phosphorylatio. Papers from a Conference. Cold Spring Harbor Laboratory, Cold Spring Harbor, New York 1981
   Google Scholar
• Thomas G., Podesta E. J., Gordon J. Protein Phosphorylation and Bio-Regulation. S. Karger, Basel 1980
   Google Scholar
• Perlmann G. E. The nature of phosphorus linkages in phosphoprotein. Adv. Protein Chem. 1955; 10: 1
   PubMedGoogle Scholar
• Taborsky G. Phosphoprotein. Adv. Protein Chem. 1974; 28: 1
   PubMedGoogle Scholar
• Chabrier P., Carayon-Gentil A. Préparation des dérivés phosphorylés des amino-acides naturel. Produit Pharm. 1962; 17: 397
   PubMedGoogle Scholar
• Mellander O. Phosphopeptides: Chemical properties and their possible role in the intestinal absorption of metal. The Transfer of Calcium and Strontium across Biological Membranes, R. H. Wasserman. Academic Press, New York 1963; 265: 295
   Google Scholar
• Österberg R. Phosphorylated Peptides: Study of Primary Structure and Metal Complexity. Almqvist & Wiksells, Uppsala 1966
   Google Scholar
• Bechhold H. Über Phosphorsäureester von Eieralbumi. Z. Physiol. Chem. 1901; 34: 122
   Google Scholar
• Neuberg C., Oertel W. Über die Einführung von Phosphorsäure in Aminosäuren, Peptone, Albumosen und Protein. Biochem. Z. 1914; 60: 491
   Google Scholar
• Langheld K. Über Metaphosphorsäure-äthylester und dessen Anwendung in der organischen Chemi. Ber. 1910; 43: 1857
   Google Scholar
• Langheld K. Über Ester und Amide der Phosphorsäuren. II. Uber Versuche zur Darstellung den Lecithinen verwandter Körpe. Ber. 1911; 44: 2076
   Google Scholar
• Neuberg C., Pollak H. Über die Phosphorylierung von Eiweiss und die Bindung des Phosphors in den natürlichen Phosphorproteine. Biochem. Z. 1910; 26: 529
   Google Scholar
• Posternak T., Grafl S. De la protection contre l'hydrolyse enzymatique exercée par les groupes phosphoryles. II. Sur la préparation de quelques peptides dérivés de la phosphotyrosine et sur leur dégradation enzymatiqu. Helv. Chim. Acta 1945; 28: 1258
   Web of Science ®Google Scholar
• Fölsch G. Synthesis of phospho-peptides. O-Phospho-dl-serylglycin. Acta Chem. Scand. 1955; 9: 1039
   Google Scholar
• Fölsch G., Mellander O. O-Phosphorylserin. Acta Chem. Scand. 1957; 11: 1232
   Google Scholar
• Fölsch G. Synthesis of phosphopeptides. I. Peptides of dl-serine and glycin. Acta Chem. Scand. 1958; 12: 561
   Google Scholar
• Fölsch G. Synthesis of phosphopeptides. II. O-Phosphorylated dipeptides of l-serin. Acta Chem. Scand. 1959; 13: 1407
   Google Scholar
• Fölsch G. Synthesis of phosphopeptides. III. Derivatives of d-seryl-l-leucine obtained by separation from a dl-l diastereoisomeric mixtur. Acta Chem. Scand. 1959; 13: 1422
   Google Scholar
• Fölsch G., Österberg R. The apparent acid ionization constant of some O-phosphorylated peptides and related compound. J. Biol. Chem. 1959; 234: 2298
   PubMed Web of Science ®Google Scholar
• Theodoropoulos T., Bennich H., Fölsch G., Mellander O. Action of trypsin on α-carbethoxy-l-lysyl-l-serylglycine and its O-phosphorylated analogu. Nature (London) 1959; 184: 187
   Web of Science ®Google Scholar
• Fölsch G., Österberg R. The apparent acid ionization constants of l-seryl-l-lysine, l-seryl-l-glutamic acid and their O-phosphorylated analogues. Proposed mechanism…peptide. Acta Chem. Scand. 1961; 15: 1963
   Google Scholar
• Avaeva S., Fölsch G., Strid L., Mellander O. Diserylphosphates and serylpyrophosphates. Some properties of O-pyrophosphoryl-serine peptide. Acta Chem. Scand. 1963; 17: 2718
   Google Scholar
• Fölsch G. Synthesis of phosphopeptides. V. Further dipeptides, tripeptides and O-phosphorylated derivatives of l-serin. Acta Chem. Scand. 1966; 20: 459
   PubMedGoogle Scholar
• Mellander O., Björnesjö K., Fölsch G., unpublished data cited in Ref. 23.
   Google Scholar
• Avaeva S. M., Botvinik M. M., Syromyatnikova I. F. Seryl phosphates and pyrophosphates. I. Synthesis of P1P2-dibenzyl ester of N-carbobenzoxyseryl P1,P2-dibenzyl pyrophosphate and P1,P2-bis(dimethylamide) of N-benzoylseryl P1,P2-dibenzyl pyrophosphate (Russ.. Zh. Obshch. Khim. 1964; 34: 1749
   Google Scholar
• Avaeva S. M., Botvinik M. M., Vafina M. G., Matyazh L. F. Seryl phosphates and pyrophosphates. II. Behavior of bisfmethyl ester of N-carbobenzoxyseryl) phenyl phosphate in HBr solution in organic solvents (Russ.. Zh. Obshch. Khim. 1964; 34: 1754
   Google Scholar
• Avaeva S. M., Botvinik M. M., Syromyatnikova I. F., Grigorovich V. I. Seryl phosphates and pyrophosphates. III. (Russ.. Vestn. Mosk. Univ. Khim. 1965; 20: 78
   Google Scholar
• Avaeva S. M., Syromyatnikova I. F., Grishchenko V. M., Botvinik M. M. Phosphorylation of carboxylic acids and amino acids by the action of diseryl pyrophosphate. Khim. Prir. Soedin. 1967; 3: 126
   Google Scholar
• Avaeva S. M., Kara-Murza S. N., Botvinik M. M. Seryl phosphates and pyrophosphates. Synthesis of O-pyrophospho-dl-serine and glycyl-O-pyrophosphono-dl-serine (Russ.. Zh. Obshch. Khim. 1967; 37: 1462
   Google Scholar
• Avaeva S. M., Kara-Murza S. N., Botvinik M. M. Seryl phosphates and pyrophosphates. Stability of the pyrophosphate bonds of seryl pyrophosphates (Russ.. Zh. Obshch. Khim. 1967; 37: 2190
   Google Scholar
• Avaeva S. M., Raskova N. V., Mevkh A. T. Synthesis of N-benzoyl-O-pyrophosphoserine methylamide (Russ.. Vestn. Mosk. Univ. Khim. 1968; 23: 121
   Google Scholar
• Avaeva S. M., Syromytanikova I. F., Botvinik M. M. Seryl phosphates and pyrophosphates. Some properties of diseryl pyrophosphates (Russ.. Zh. Obshch. Khim. 1968; 38: 2231
   Google Scholar
• Avaeva S. M., Sklyankina V. A., Ermolenko L. V., Botvinik M. M. Serine phosphates and pyrophosphates. Reaction of N-benzoyl-O-phosphoserine N-methylamide with hydroxylamines and meth-ylamine (Russ.. Zh. Obshch. Khim. 1968; 38: 2363
   Google Scholar
• Avaeva S. M., Sklyankina V. A., Botvinik M. M. Seryl phosphates and seryl pyrophosphates. Interaction of di(methylamido-N-benzoylseryl) pyrophosphate with hydroxylamine and methylamine (Russ. Zh. Obshch. Khim. 1968; 38: 2783
   Google Scholar
• Avaeva S. M., Sklyankina V. A., Botvinik M. M. Seryl phosphates and seryl pyrophosphates. Reaction of phosphate and amine groups in diseryl pyrophosphates (Russ.. Zh. Obshch, Khim. 1969; 39: 591
   Google Scholar
• Avaeva S. M., Raskova N. V., Botvinik M. M. Hydrolysis of N-benzoyl-O-pyrophosphoserine methylamide (Russ.. Vestn. Mosk. Univ. Khim. 1970; 11: 96
   Web of Science ®Google Scholar
• Avaeva S. M., Raskova N. V., Mevkh A. T. Synthesis of N-benzoyl-O-pyrophosphoserine methylamide (Russ.. Vestn. Mosk. Univ. Khim. 1970; 11: 100
   Web of Science ®Google Scholar
• Avaeva S. M., Sklyankina V. A., Kolesnikova V. Yu. Hydrolysis of phosphoric ester serine derivatives containing free amino or carboxylic groups (Russ.. Vestn. Mosk. Univ. Khim. 1971; 12: 627
   Web of Science ®Google Scholar
• Avaeva S. M., Sklyankina V. A. Hydrolysis of the methyl ester of O-phosphoserine (Russ. Zh. Obshch. Khim. 1971; 41: 2081
   Google Scholar
• Katchalsky A., Paecht M. Bull. Res. Counc. Isr. 1952; 2: 312
   Google Scholar
• Katchalsky A., Paecht M. Phosphate anhydrides of amino acid. J. Am. Chem. Soc. 1954; 76: 6042
   Web of Science ®Google Scholar
• Paecht M., Katchalsky A. Phosphorylation of adenylic acid by the phosphate anhydride of leucine and chromatographic analysis of the resulting product. J. Am. Chem. Soc. 1954; 76: 6197
   Web of Science ®Google Scholar
• Paecht M., Katchalsky A. Spontaneous de-amination of amino-acid phosphates under physiological condition. Nature (London) 1959; 184: 1489
   PubMed Web of Science ®Google Scholar
• Paecht M., Katchalsky A. Aspartic acid formation from glycine phosphat. Biochim. Biophys. Acta. 1964; 90: 260
   PubMed Web of Science ®Google Scholar
• Katchalsky A., Ailam G. Polycondensation of amino acid phosphoanhydrides. I. Theoretica. Biochim. Biophys. Acta 1967; 140: 1
   Web of Science ®Google Scholar
• Paecht-Horowitz M., Katchalsky A. Polycondensation of amino acid phosphoanhydrides. II. Polymerization of proline adenylate at constant phosphoanhydride concentratio. Biochim. Biophys. Acta 1967; 140: 14
   Web of Science ®Google Scholar
• Lewisohn R., Paecht-Horowitz M., Katchalsky A. Polycondensation of amino acid phosphoanhydrides. III. Polycondensation of alanyl adenylat. Biochim. Biophys. Acta 1967; 140: 24
   Web of Science ®Google Scholar
• Winnick T., Scott E. M. Phosphorylated amino acid. Arch. Biochem. 1947; 12: 201
   PubMedGoogle Scholar
• Patil S. S., Youngblood P., Christiansen P., Moore R. E. Phaseotoxin A: An antimetabolite fro. Pseudomonas phaseolicola, Biochem. Biophys. Res. Commun. 1976; 69: 1019
   PubMed Web of Science ®Google Scholar
• Mitchell R. E. Bean halo blight: Comparison of phaseolotoxin and N-phosphoglutamat. Physiol. Plant Pathol. 1979; 14: 119
   Google Scholar
• Smith A. G., Rubery P. H. N-Phosphoglutamate does not behave as an active component of the exotoxin of Pseudomonas phaseolicola, the causative agent of haloblight of bean. Physiol. Plant Pathol. 1979; 15: 269
   Google Scholar
• Chung N. M., Lohrmann R., Orgel L. E., Rabinowitz J. The mechanism of the trimetaphosphate-induced peptide synthesi. Tetrahedron 1971; 27: 1205
   Web of Science ®Google Scholar
• Severin S. E., Yudelovich R. Ya. Synthesis and properties of phosphorylated β-alanine, l-histidine, and α-alanine (Russ.. Biokhimiya 1947; 12: 105
   Google Scholar
• Binkley F. Preparation and properties of S-phosphocystein. J. Biol. Chem. 1952; 195: 283
   PubMed Web of Science ®Google Scholar
• Gustafson C., Wagner-Jauregg T. Phosphoimidazole and phosphohistidin. Fed. Proc. Fed. Am. Soc. Exp. Biol. 1954; 13: 222
   Google Scholar
• DeLuca M., Ebner K. E., Hultquist D. E., Kreil G., Peter J. B., Moyer R. W., Boyer P. D. The isolation and identification of phosphohistidine from mitochondrial protei. Biochem. Z. 1963; 338: 512
   PubMedGoogle Scholar
• Hultquist D. E. The preparation and characterization of phosphorylated derivatives of histidin. Biochim. Biophys. Acta 1968; 153: 329
   PubMed Web of Science ®Google Scholar
• Zetterqvist O., Engström L. Isolation of N°-[32P]phosphoryl-lysine from rat-liver cell sap after incubation with [32P]adenosine triphosphat. Biochim. Biophys. Acta 1967; 141: 523
   PubMed Web of Science ®Google Scholar
• Nordmann J., Mattioda G., Loiseau G. Nouveaux Médicaments à Base de Dérivés Phosphorylés de la Lysin. French Patent M7690 1970
   Google Scholar
• Fujitaki J. M., Steiner A. W., Nichols S. E., Helander E. R., Lin Y. C., Smith R. A. A simple preparation of N-phosphorylated lysine and arginin. Prep. Biochem. 1980; 10: 205
   PubMed Web of Science ®Google Scholar
• Bamann E., Sanchez L. F., Trapmann H. Lósung der N—P-Bindung in Phosphoamiden durch seltene Erdmetall. Chem. Ber. 1955; 88: 1846
   Google Scholar
• Thiem Ng. V., Thoai Ng. V., Roche J. Synthese de l'argininephosphat. Bull. Soc. Chim. Biol. 1962; 44: 284
   Google Scholar
• Marcus F., Morrison J. F. The preparation of phosphoarginine: A comparative stud. Biochem. J. 1964; 92: 429
   PubMed Web of Science ®Google Scholar
• Willmitzer L., Wagner K. G. Chemical synthesis of partially and fully phosphorylated protamine. Eur. J. Biochem. 1975; 59: 43
   PubMedGoogle Scholar
• Neuhaus F. C., Korkes S. Phosphoserin. Biochem. Preparations 1958; 6: 75
   Google Scholar
• Kawashima H., Yamada Y. Hydroxyamino Acid Phosphate Ester. Japanese Patent 1980; 44: 080
   Google Scholar
• Samuel D., Silver B. L. Elimination reactions and hydrolysis of serine phosphat. J. Chem. Soc. 1963; 289
   Google Scholar
• Mohan M. S., Abbott E. H. Catalytic dephosphorylation of O-phosphoserine by glyoxylate ion and copper(II. Inorg. Chem. 1978; 17: 3083
   Web of Science ®Google Scholar
• Rimington C. Phosphorylation of protein. Biochem. J. 1927; 21: 272
   PubMedGoogle Scholar
• Boursnell J. C., Dewey H. M., Wormall A. The chemical and immunological properties of phosphorylated protein. Biochem. J. 1948; 43: 84
   PubMed Web of Science ®Google Scholar
• Salak J., Vodrazka Z., Cejka J. Phosphorylation of human serum albumin and haemoglobi. Coll. Czech. Chem. Commun. 1965; 30: 1036
   Google Scholar
• Banks T. E., Boursnell J. C., Dewey H. M., Francis G. E., Tupper R., Wormall A. The use of radioactive isotopes in immunological investigations. II. The fate of injected 32P-containing protein. Biochem. J. 1948; 43: 518
   PubMed Web of Science ®Google Scholar
• Woo S. L., Creamer L. K., Richardson T. Chemical phosphorylation of bovine β-lactoglobuli. J. Agric. Food Chem. 1982; 30: 65
   PubMed Web of Science ®Google Scholar
• Mayer M., Heidelberger M. Physical, chemical and immunological properties of phosphorylated crystalline horse serum albumi. J. Am. Chem. Soc. 1946; 68: 18
   PubMed Web of Science ®Google Scholar
• Heidelberger M., Davis B., Treffers H. P. Phosphorylated egg albumi. J. Am. Chem. Soc. 1941; 63: 498
   Google Scholar
• Levene P. A., Schormüller A. Synthesis of the phosphoric esters of hydroxyamino acids. II. The synthesis of dl-serinephosphoric aci. J. Biol Chem. 1934; 150: 547
   Google Scholar
• Levene P. A., Schormüller A. The synthesis of tyrosinephosphoric aci. J. Biol. Chem. 1933; 100: 583
   Google Scholar
• Bennett R., Burger A., Gemmill C. L. O-Phosphoric acid esters of 3,5-diiodotyrosine and thyroxin. J. Med. Pharm. Chem. 1960; 2: 493
   Google Scholar
• Wagner-Jauregg T., O'Neill J. J., Summerson W. H. The reaction of phosphorus-containing enzyme inhibitors with amines and amino acid derivative. J. Am. Chem. Soc. 1951; 73: 5202
   Web of Science ®Google Scholar
• Lies T., Plapinger R. E., Wagner-Jauregg T. The preparation of N-dialkylphosphorylated glycin. J. Am. Chem. Soc. 1953; 75: 5755
   Web of Science ®Google Scholar
• Zervas L., Katsoyannis P. G. N-Phosphoroamino acids and peptide. J. Am. Chem. Soc. 1955; 77: 5351
   Google Scholar
• Alimov P. I., Fedorova O. N., Cheplanova I. V. Synthesis and properties of some mixed N-substituted phosphoramidates (Russ.. Izv. Kazan. Fil. Akad. Nauk S.S.S.R., Ser. Khim. Nauk 1957; 49
   Google Scholar
• Alimov P. I., Fedorova O. N. Preparation of amides of N-phosphorylated amino carboxylic acids (Russ.. Izv. Kazan. Fil. Akad. Nauk S.S.S.R., Ser. Khim. Nauk 1961; 48
   Google Scholar
• Plapinger R. E., Wagner-Jauregg T. A nitrogen-to-oxygen phosphoryl migration: Preparation of dl-serinephosphoric and threoninephosphoric aci. J. Am. Chem. Soc. 1953; 75: 5757
   Web of Science ®Google Scholar
• Holzer M. E., Burrow D. J., Smith R. A. Metabolism of phosphoramidates. I. Enzymic hydrolysis and transfer reaction. Biochim. Biophys. Acta 1962; 56: 491
   PubMedGoogle Scholar
• Li S.-O. Synthesis of N-phosphoryl amino acid ester. J. Am. Chem. Soc. 1952; 74: 5959
   Web of Science ®Google Scholar
• Li S.-O., Eakin R. E. Synthesis of N-phosphorylated derivatives of amino acid. J. Am. Chem. Soc. 1955; 77: 1866
   Web of Science ®Google Scholar
• Clark V. M., Macrae A. R., Richter J. F. P. Lord Todd, (N-Phosphoro)-α-amino acid. Tetrahedron Suppl. 1966; 307
   Google Scholar
• Sciarini L. J., Fruton J. S. Derivatives of N-phosphorylated amino acid. J. Am. Chem. Soc. 1949; 71: 2940
   Web of Science ®Google Scholar
• Bernton A. Diphenyl-phosphorsäure, ein Reagens auf Aminogruppe. Ber. 1922; 55: 3361
   Google Scholar
• Li S.-O., Eakin R. E. Infrared spectra of N-phosphorylated derivatives of amino acid. J. Am. Chem. Soc. 1955; 77: 3519
   Web of Science ®Google Scholar
• Cosmatos A., Photaki I., Zervas L. Peptidsynthesen über N-Phosphorylaminosäure-phosphorsäure-anhydrid. Chem. Ber. 1961; 94: 2644
   Google Scholar
• Sampson E. J., Fedor J., Benkovic P. A., Benkovic S. J. Intramolecular and divalent metal ion catalysis. The hydrolytic mechanism of O-phenyl N-(glycyl)phosphoramidat. J. Org. Chem. 1973; 38: 1301
   PubMed Web of Science ®Google Scholar
• Saias E., Kornowski S. H. Nouveau Dérivé Phosphoryle de l'Acide l-Aspartique et Procédé de Préparation, French Patent 1,488,42. 1967
   Google Scholar
• Cramer F., Scheiffele E., Vollmar A. Zur Chemie der “energiereichen” Phosphate. XVI. Die Synthese der Argininphosphorsäure und die Reaktion von Isoureidophosphonaten mit Amine. Chem. Ber. 1962; 95: 1670
   Google Scholar
• Kam C.-M., Nishino N., Powers J. C. Inhibition of thermolysin and carboxypeptidase A by phosphoramidate. Biochemistry 1979; 18: 3032
   PubMed Web of Science ®Google Scholar
• Khatri H. N., Stammer C. H., Bradford M. M., McRorie R. A. The synthesis of some N-phosphoryldipeptide aldehyde. Biochim. Biophys. Res. Commun. 1980; 96: 163
   PubMed Web of Science ®Google Scholar
• Alimov P. I., Fedorova O. N. N-Phosphorylation of glycine and some of its derivatives (Russ.. Izv. Akad. Nauk S.S.S.R., Ser. Khim. 1966; 1370
   Google Scholar
• Theodoropoulos D., Gazopoulos J., Souchleris I. Synthesis of phosphoserine and certain phosphorylated peptides by transphosphorylatio. J. Chem. Soc. 1960; 5257
   Google Scholar
• Riley G., Turnbull J. H., Wilson W. Synthesis of some phosphorylated amino-hydroxy-acids and derived peptides related to the phosphoprotein. J. Chem. Soc. 1957; 1373
   Google Scholar
• Bevan T. H., Malkin T., Tiplady J. M. A new synthesis of phosphatidylserine and the preparation of serine and 2-aminoethyl (“ethanolamine”) phosphate ester. J. Chem. Soc. 1957; 3086
   Google Scholar
• Theodoropoulos D., Souchleris I. Further synthetic studies with phosphorylated peptide. Biochemistry 1964; 3: 145
   PubMed Web of Science ®Google Scholar
• Theodoroupoulos D., Gazopoulos J., Souchleris I. New approach to the synthesis of O-phosphoserine and related peptide. Nature (London) 1960; 185: 606
   Web of Science ®Google Scholar
• Chantrenne H. Synthèses peptidiques a partir d'un dérivé du glycylphosphat. Biochim. Biophys. Acta 1950; 4: 484
   Web of Science ®Google Scholar
• Sheehan J. C., Frank V. S. Peptide syntheses using energy-rich phosphorylated amino acid derivative. J. Am. Chem. Soc. 1950; 72: 1312
   Web of Science ®Google Scholar
• Ueki M., Ikeda S. Phosphinyl- and phosphinothioylamino acids and peptides. I. Preparation of diphenylphosphinothioyl(Ppt)-amino acid. Chem. Lett. 1976; 827
   Google Scholar
• Ikeda S., Tonegawa F., Shikano E., Shinozaki K., Ueki M. Phosphinyl- and phosphinothioyl-amino acids and peptides. IV. Further examples of use of the diphenylphosphinothioyl group for the protection of amino acid. Bull. Chem. Soc. Jpn. 1979; 52: 1431
   Web of Science ®Google Scholar
• Keller H., Netter H., Niemann B. Über innere Phosphoaminosäureanhydrid. Z. Physiol. Chem. 1958; 313: 244
   PubMedGoogle Scholar
• Bourland E., Pacht M. Phosphorylation par le phénylphosphodichlorure de groupements hydroxylés. I. Acides aminés et composés hydroxylés ou aminés simple. Bull. Soc. Chim. Biol. 1951; 33: 681
   PubMedGoogle Scholar
• Grabar P., Pacht M., Bourland E. Phosphorylation par le phénylphosphodichlorure de groupements hydroxylés. II. Protéide. Bull. Soc. Chim. Biol. 1951; 33: 690
   PubMedGoogle Scholar
• Jones E. E., Lipkin D. Serine and ethanolamine diesters of orthophosphoric aic. J. Am. Chem. Soc. 1956; 78: 2408
   Web of Science ®Google Scholar
• Aubel E., Reich W. S. Préparation synthétique des dérivés phosphorylés des aminoacide. C. R. 1932; 195: 183
   Google Scholar
• De Haas G. H., Van Zutphen H., Bonsen P. P. M., Van Deenen L. L. M. Synthesis of mixed-acid phosphatidylserine containing unsaturated fatty acid. Rec. Trav. Chim. 1964; 83: 99
   Google Scholar
• Bentler M., Netter H. Synthesis of amino acid phosphoric acid anhydride. Z. Physiol. Chem. 1953; 295: 362
   PubMedGoogle Scholar
• Holzer M. E., Johnson K. D., Smith R. A. Metabolism of phosphoramidates. III. A microsomal phosphoramidate hexose transfer syste. Biochim. Biophys. Acta 1966; 122: 232
   PubMed Web of Science ®Google Scholar
• Avaeva S. M., Botvinik M. M., Syromyatnikova I. F. Serylphosphates and pyrophosphates. V. Synthesis of serine, glycylserine, and N-benzoylserine methylamide pyrophosphates (Russ.. Sintez Prirodn. Soedin., ikh Analogov i Fragmentov, Akad. Nauk S.S.S.R., Otd. Obshch. i Tekhn. Khim. 1965; 154
   Google Scholar
• Ullman B., Perlman R. L. Chemically phosphorylated protamine: A new substrate for the study of phosphoprotein phosphatase activit. Biochem. Biophys. Res. Commun. 1975; 63: 424
   PubMed Web of Science ®Google Scholar
• Hatanaka H., Egami F. The formation of amino acids and related oligomers from formaldehyde and hydroxylamine in modified sea mediums related to prebiotic condition. Bull. Chem. Soc. Jpn. 1977; 50: 1147
   Web of Science ®Google Scholar
• Black S., Wright N. G. β-Aspartokinase and β-aspartyl phosphat. J. Biol. Chem. 1955; 213: 27
   PubMed Web of Science ®Google Scholar
• Canali V., Casciotti G., De Luca R., Baldantoni A. Sintesi dell acido serin fosforic. Boll. Soc. Ital. Biol. Sper. 1951; 27: 1479
   PubMedGoogle Scholar
• Ferrel R. E., Olcott H. S., Fraenkel-Conrat H. Phosphorylation of proteins with phosphoric acid containing excess phosphorus pentoxid. J. Am. Chem. Soc. 1948; 70: 2101
   PubMed Web of Science ®Google Scholar
• Liebig H., Dransch G. Verfahren zur Herstellung von O-Serinphosphat, German Patent 1,151,810. 1963
   Google Scholar
• Plimmer R. H. A. Esters of phosphoric acid. IV. Phosphoryl hydroxyamino-acid. Biochem. J. 1941; 35: 461
   PubMedGoogle Scholar
• Österberg R. Metal complexes of O-phosphorylserin. Arkiv. Kemi 1959; 13: 393
   Google Scholar
• Rabinowitz J., Flores J., Krebsbach R., Rogers G. Peptide formation in the presence of linear or cyclic polyphosphate. Nature (London) 1969; 224: 795
   PubMed Web of Science ®Google Scholar
• De Verdier C.-H. The isolation of phosphothreonine from bovine casei. Acta Chem. Scand. 1953; 7: 196
   Google Scholar
• Levene P. A., Schormüller A. Synthesis of the prosphoric esters of hydroxyamino acids. III. Resolution of dl-serinephosphoric acid and synthesis of l-hydroxyprolinephosphoric aci. J. Biol. Chem. 1934; 106: 595
   Google Scholar
• Mitchell H. K., Lunan K. D. Tyrosine-O-phosphate i. Drosophila, Arch. Biochem. Biophys. 1964; 106: 219
   PubMed Web of Science ®Google Scholar
• Cherbuliez E., Rabinowitz J. Recherches…IX. Sur la phosphorylation des hydroxy-acides par les acides polyphosphorique. Helv. Chim. Acta 1956; 39: 1461
   Web of Science ®Google Scholar
• Murray K., Milstein C. Esters of serine and threonine in hydrolysates of histones and protamines, and attendant errors in amino acid analyses of protein. Biochem. J. 1967; 105: 491
   PubMed Web of Science ®Google Scholar
• Tsuhako M., Fujita N., Nakahama A., Matsuo T., Kobayashi M., Ohashi S. The reaction of cyclo-triphosphate with l-valin. Bull. Chem. Soc. Jpn. 1980; 53: 1968
   Web of Science ®Google Scholar
• Tsuhako M., Fujita N., Nakahama A., Matsuo T., Kobayashi M., Ohashi S. The reaction of cyclo-tetraphosphate with l-valin. Bull. Chem. Soc. Jpn. 1981; 54: 289
   Web of Science ®Google Scholar
• Porihosu Kagaku Kenkyusho K. K. Aminophosphoric Acid Salts from Cyclic Phosphoric Acid Salts and Amino Acid. Japanese Patent 1980; 66: 597
   Google Scholar
• Sung H. Y., Chen H. J., Liu T. Y., Su J. C. Improvement of the functionalities of soy protein isolate through chemical phosphorylatio. J. Food. Sci. 1983; 48: 716
   Web of Science ®Google Scholar
• Plimmer R. H. A., Burch W. J. N. Esters of phosphoric acid. II. The action of ethyl metaphosphate on alcohols, ammonia, and some amino-compound. J. Chem. Soc. 1929; 292
   Google Scholar
• Jencks W. P., Gilchrist M. Reactions of nucleophilic reagents with phosphoramidat. J. Am. Chem. Soc. 1965; 87: 3199
   Web of Science ®Google Scholar
• Rathlev T., Rosenberg T. Non-enzymic formation and rupture of phosphorus to nitrogen linkages in phosphoramido derivative. Arch. Biochem Biophys. 1956; 65: 319
   PubMed Web of Science ®Google Scholar
• Hultquist D. E., Moyer R. W., Boyer P. D. The preparation and characterization of 1-phosphohistidine and 3-phosphohistidin. Biochemistry 1966; 5: 322
   PubMed Web of Science ®Google Scholar
• Nordmann J., Mattioda G. Nouveau Médicament à Propriétés Antifatigues et Cardiotonique. French Patent M3936 1966
   Google Scholar
• Steiner A. W., Helander E. R., Fujitaki J. M., Smith L. S., Smith R. A. High-performance liquid chromatography of acid-stable and acid-labile phosphoamino acid. J. Chromatogr. 1980; 202: 263
   PubMed Web of Science ®Google Scholar
• Fujitaki J. M., Fung G., Oh E. Y., Smith R. A. Characterization of chemical and enzymatic acid-labile phosphorylation of histone H4 using phosphorus-31 nuclear magnetic resonanc. Biochemistry 1981; 20: 3658
   PubMed Web of Science ®Google Scholar
• Gassner M., Stehlik D., Schrecker O., Hengstenberg W., Maurer W., Rüterjans H. The phosphornolpyruvate-dependent phosphotransferase system of Staphylococcus aureus. II. 1H and 31P nuclear-magnetic-resonance studies on the phosphocarrier protein HPr, phosphohistidines and phosphorylated HP. Eur. J. Biochem. 1977; 75: 287
   PubMedGoogle Scholar
• Stevens-Clark J. R., Conklin K. A., Fujimoto A., Smith R. A. Phosphoramidates. VII. Determination of kinetic parameters and substrate interrelationships for the phosphoryl transfer enzyme fro. Escherichia coli, J. Biol. Chem. 1968; 243: 4474
   PubMed Web of Science ®Google Scholar
• Rosenberg T. A simple preparation method for diphosphoimidazol. Arch. Biochem. Biophys. 1964; 105: 315
   PubMed Web of Science ®Google Scholar
• Guibé-Jampel E., Wakselman M., Vilkas M. Dérivés “acylés” du N-méthyl imidazole. I. Réaction du chlorure de N-phosphoryl N′-méthyl imidazolium avec les amines. Préparation de monophosphoramides e milieu aqueu. Bull. Soc. Chim. Fr. 1971; 1308
   Google Scholar
• Rosenberg E. T. 1959, Diphosphoimidazoles, U.S. Patent 2,917,517
   Google Scholar
• Felcht U., Regitz M. Phosphorylierung mit l-Phosphorylpyrazolen, III. N-Phosphorylierng von Aminen, Glycin-ethylester, Hydrazin, Hydrazonen und Natriumazi. Ann. Chem. 1977; 1309
   Google Scholar
• Trapmann H. Phosphatabspaltung bei N-phosphorylierten Aminosäuren in Gegenwart von Ionen seltener Erdmetall. Naturwissenschaften 1959; 46: 141
   Google Scholar
• Sakhatskaya T. S. Heat changes of hydrolysis of phosphorylated carnosine, β-alanine, and l-histidine (Russ.. Biokhimiya 1947; 12: 163
   Google Scholar
• Rozhanskii M. E. Determination of hydrolysis constants of some phosphoamino acids and phosphodi-peptides (Russ.. Biokhimiya 1952; 17: 222
   PubMedGoogle Scholar
• Bylund D. B., Huang T. S. Decomposition of phosphoserine and phosphothreonine during acid hydrolysi. Anal. Biochem. 1976; 73: 477
   PubMed Web of Science ®Google Scholar
• Schaffer N. K., Balakir R. A. Decomposition of serine during acid hydrolysis of phosphorylserin. Anal. Biochem. 1966; 14: 167
   Web of Science ®Google Scholar
• Bamann E., Trapmann H., Schuegraf A. Metallkatalytische Spaltung von Phosphoproteide. Chem. Ber. 1955; 88: 1726
   Google Scholar
• Belec J., Jenness R. Dephosphorization of phosvitin and caseins by heatin. Biochim. Biophys. Acta 1962; 63: 512
   PubMed Web of Science ®Google Scholar
• Daley L. S., Bidwell R. G. S. Separation of phosphohydroxypyruvate, 3-phosphoglyceric acid and O-phosphoserine by paper chromatography and chemical derivatizatio. J. Chromatogr. 1978; 147: 233
   Web of Science ®Google Scholar
• White A. Effect of pH on fluorescence of tyrosine, tryptophan and related compound. Biochem. J. 1959; 71: 217
   PubMed Web of Science ®Google Scholar
• Morita M., Kakuta I., Fujimaki M. Radiation-induced cleavage of esters of phosphoric acid in aqueous solution. Agric. Biol. Chem. 1972; 36: 1069
   Web of Science ®Google Scholar
• Samuni A., Neta P. Hydroxyl radical reaction with phosphate esters and the mechanism of phosphate cleavag. J. Phys. Chem. 1973; 77: 2425
   Web of Science ®Google Scholar
• Mohan M. S., Abbott E. H. Metal complexes of amino acid phosphate ester. Inorg. Chem. 1978; 17: 2203
   Web of Science ®Google Scholar
• Mohan M. S., Bancroft D., Abbott E. H. Mixed-ligand complexes of O-phospho-dl-serin. Inorg. Chem. 1979; 18: 2468
   Web of Science ®Google Scholar
• Hendrickson H. S., Fullington J. G. Stabilities of metal complexes of phospholipids: Ca(II), Mg(II), and Ni(II) complexes of phosphatidylserine and triphosphoinositid. Biochemistry 1965; 4: 1599
   PubMed Web of Science ®Google Scholar
• Childs C. W. Calcium(II) and magnesium(II) binding by l-serine orthophosphate in aqueous solution. Can. J. Chem. 1971; 49: 2359
   Web of Science ®Google Scholar
• Merrill D. K., McAlexander J. C., Guynn R. W. Equilibrium constants under physiological conditions for the reactions of d-3-phosphoglycerate dehydrogenase and l-phosphoserine aminotransferas. Arch. Biochem. Biophys. 1981; 212: 717
   PubMed Web of Science ®Google Scholar
• Österberg R. Calcium, magnesium, and manganese(II) complexes of some O-phosphorylated peptide. Acta Chem. Scand. 1962; 16: 2434
   Google Scholar
• Österberg R. The metal complexes of peptides and related compounds. II. Copper(II) complexes of O-phosphorylserylglycine in aqueous solutio. Arkiv. Kemi 1965; 25: 177
   Google Scholar
• Österberg R. The metal complexes of peptides and related compounds. I. Copper(II) complexes of O-phosphorylserylglutamic acid in aqueous solutio. Acta Chem. Scand. 1965; 19: 1445
   PubMedGoogle Scholar
• Che T. M., Kustin K. Kinetics of Ni(II) and Co(II) monocomplex formation with O-phospho-dl-serin. J. Inorg. Biochem. 1980; 13: 267
   Web of Science ®Google Scholar
• Gresh N. Intermolecular chelation of two serine phosphates by Ca2+ and Mg2+. A theoretical structural investigatio. Biochim. Biophys. Acta 1980; 597: 345
   PubMed Web of Science ®Google Scholar
• Tatsumoto K., Martell A. E., Motekaikis R. J. Reaction kinetics and equilibria of β-elimination of some Schiff base complexe. J. Am. Chem. Soc. 1981; 103: 6197
   Web of Science ®Google Scholar
• Tatsumoto K., Martell A. E. Catalysis of the β elimination of O-phosphoserine and β-chloroalanine by pyridoxal and zinc(II) io. J. Am. Chem. Soc. 1977; 99: 6082
   Web of Science ®Google Scholar
• Longenecker J. B., Snell E. E. The comparative activities of metal ions in promoting pyridoxal-catalyzed reactions of amino acid. J. Am. Chem. Soc. 1957; 79: 142
   Web of Science ®Google Scholar
• Longenecker J. B., Snell E. E. Pyridoxal and metal ion catalysis of α,β elimination reactions of serine-3-phosphate and related compound. J. Biol. Chem. 1957; 225: 409
   PubMed Web of Science ®Google Scholar
• Thomas J. H., Dodgson K. S., Tudball N. The pyridoxal- and pyridoxal 5′-phosphate-catalysed non-enzymic degradations of l-serine O-sulphate and related compound. Biochem. J. 1968; 110: 687
   PubMed Web of Science ®Google Scholar
• Mohan M. S., Siegel R., Abbott E. H. Mixed metal ion catalysis of the elimination of phosphate ion from phosphoserine-pyridoxal Schiff base. Indian J. Chem. Sect. A 1980; 19A: 363
   Google Scholar
• Murakami Y., Kondo H., Martell A. E. Catalysis of the β-elimination of O-phosphothreonine by pyridoxal and metal ion. J. Am. Chem. Soc. 1973; 95: 7138
   PubMed Web of Science ®Google Scholar
• Dalling D. K., Grant D. M., Horton W. J., Sagers R. D. Carbon 13 NMR study of nonenzymatic reactions of pyridoxal 5′-phosphate with selected amino acids and of related reaction. J. Biol. Chem. 1976; 251: 7661
   PubMed Web of Science ®Google Scholar
• Ratsisalovanina O., Chapeville F., Fromageot P. Synthèses d'acides aminés soufrés à partir de cystéine, de sérine et de phosphosérine, catalysées par le pyridoxal et un méta. Biochim. Biophys. Acta 1961; 49: 322
   PubMed Web of Science ®Google Scholar
• Fromageot P., Roderick U. R., Pouzat J. Synthèse nonenzymatique de l'acide cystéique à partir de quelques acides aminés β-substitués, de pyruvate, de sulfite et d'ions cuivr. Biochim. Biophys. Acta 1963; 78: 126
   PubMed Web of Science ®Google Scholar
• Griffin M., Price S. J., Palmer T. A rapid and sensitive procedure for the quantitative determination of plasma amino acid. Clin. Chim. Acta 1982; 125: 89
   PubMed Web of Science ®Google Scholar
• Pogliani L., Ziessow D., Krüger C. 1H and 13C NMR study of phosphopeptides. I. Acetylphos-phoserine and acetylphosphothreonin. Tetrahedron 1979; 35: 2867
   Google Scholar
• Cherbuliez E., Espejo O., Willhalm B., Rabinowitz J. Recherches. LXXIX. Sur la réaction de l'isothiocyanate d'o-methoxycarbonyl-phényle avec divers acides et l'acide sérinephosphoriqu. Helv. Chim. Acta 1968; 51: 241
   PubMed Web of Science ®Google Scholar
• Shieh J.-J., Desiderio D. M. Derivatives for characterization of phosphoserine and phosphothreonine by gas chromatography-mass spectrometr. Anal. Lett. 1977; 10: 831
   Web of Science ®Google Scholar
• Putkey E., Sundaralingam M. Molecular structures of amino acids and peptides. I. The crystal structure and conformation of dl-O-serine phosphate monohydrate. Very short phosphate-phosphate hydrogen bond. Acta Crystallogr. 1970; B26: 782
   Google Scholar
• Sundaralingam M., Putkey E. F. Molecular structures of amino acids and peptides. II. A redetermination of the crystal structure of l-O-serine phosphate. A very short phosphate-carboxyl hydrogen bon. Acta Crystallogr. 1970; B26: 790
   Google Scholar
• Hirtz J., Bouthors D., Gerardin A., Vassort P. Application de la thermogravimétrie à l'étude de la solvatation des produits organiques d'intérět pharmaceutiqu. Ann. Pharm. Fr. 1968; 26: 749
   PubMedGoogle Scholar
• Anon. Sadtler Standard Spectra. Sadtler Research Laboratories, Philadelphia 1982
   Google Scholar
• Mitchell H. K., Chen P. S., Hadorn E. Tyrosine phosphate on paper chromatograms o. Drosophila melanogaster, Experientia 1960; 16: 410
   Google Scholar
• Asso M. Étude par RMN des complexes de la phosphosérine et de la phosphoéthanolamine avec les lanthanide. Rev. Chim. Miner. 1975; 12: 120
   Google Scholar
• Asso M., Mossoyan J., Benlian D., François A. Conformation des complexes de lanthanides avec la l-phosphosérine et la phosphoéthanolamine en phase aqueus. J. Chim. Phys. Phys.-Chim. Biol. 1976; 73: 315
   Google Scholar
• Pogliani L., Ziessow D., Krüger C. Conformational study of phosphoserine in aqueous solutions. II. 1H N.m.r. result. Org. Magn. Resonance 1977; 10: 26
   Web of Science ®Google Scholar
• Bolton P. H. Investigation of phosphoserine and cytidine 5′-phosphate by heteronuclear two-dimensional spectroscopy: Samples with strong proton couplin. J. Magn. Resonance 1981; 45: 239
   Web of Science ®Google Scholar
• Pogliani L., Ziessow D. Conformational study of phosphothreonine in aqueous solution. 1H and 13C NMR result. Org. Magn. Resonance 1978; 11: 319
   Web of Science ®Google Scholar
• Bolton P. H. Heteronuclear two-dimensional NMR as a conformational probe of cellular phosphate. presented at the Symp. Biomolec. Stereodynamics, Albany, NY, April 26 to 29, 1981, 437
   Google Scholar
• Vogel H. J., Bridger W. A. A phosphorus 31 nuclear magnetic resonance study of the intermediates of the Escherichia coli succinyl coenzyme A synthetase reaction. Evidence for substrate synergism and catalytic cooperativit. J. Biol. Chem. 1982; 257: 4834
   PubMed Web of Science ®Google Scholar
• Rao B. D. N., Cohn M. 31P nuclear magnetic resonance of bound substrates of arginine kinase reaction. Chemical shifts in binary, ternary, quaternary, and transition state analog complexe. J. Biol. Chem. 1977; 252: 3344
   PubMed Web of Science ®Google Scholar
• Ho C., Kurland R. J. Phosphorus nuclear magnetic resonance study of phosphoproteins. I. Chemical nature of phosphorus atoms in bovine αs-casei. J. Biol. Chem. 1966; 241: 3002
   PubMed Web of Science ®Google Scholar
• Ho C., Magnuson J. A., Wilson J. B., Magnuson N. S., Kurland R. J. Phosphorus nuclear magnetic resonance studies of phosphoproteins and phosphorylated molecules. II. Chemical nature of phosphorus atoms in αs-casein B and phosviti. Biochemistry 1969; 8: 2074
   PubMed Web of Science ®Google Scholar
• Chlebowski J. F., Armitage I. M., Tusa P. P., Coleman J. E. 31P NMR of phosphate and phosphonate complexes of metalloalkaline phosphatase. J. Biol. Chem. 1976; 251: 1207
   PubMed Web of Science ®Google Scholar
• Kohler S. J., Klein M. P. 31P Nuclear magnetic resonance chemical shielding tensors of phos-phorylethanolamine, lecithin, and related compounds: Applications to head-group motion in model membrane. Biochemistry 1976; 15: 967
   PubMed Web of Science ®Google Scholar
• Kohler S. J., Klein M. P. Phosphoms-31 nuclear magnetic resonance chemical shielding tensors of l-O-serine phosphate and 3′-cytidine monophosphat. J. Am. Chem. Soc. 1977; 99: 8290
   PubMed Web of Science ®Google Scholar
• Pogliani L., Ziessow D., Krüger C. Confomational study of phosphoserine in aqueous solution. I. 13C N.m.r. result. Org. Magn. Resonance 1977; 9: 504
   Web of Science ®Google Scholar
• James T. L., Noggle J. H. 23Na NMR studies of sodium ion interactions: Phosphatidyl serine, phosphoserine, and phosphoethanolamin. Anal. Biochem. 1972; 49: 208
   PubMed Web of Science ®Google Scholar
• Kostelnik R. J., Bothner-By A. A. Cadmium-113 nuclear magnetic resonance studies of cad-mium(II)-ligand binding in aqueous solutions. I. The effect of diverse ligands on the cadmium-113 chemical shif. J. Magn. Resonance 1974; 14: 141
   Web of Science ®Google Scholar
• Vogel H. J., Bridger W. A., Sykes B. D. Frequency-dependent phosphorus-31 nuclear magnetic resonance studies of the phosphohistidine residue of succinyl-CoA synthetase and the phosphoserine residue of glycogen phosphorylase . Biochemistry 1982; 21: 1126
   PubMed Web of Science ®Google Scholar
• McCallum G. H., Robertson J. M., Sim G. A. Crystal structure of l-serine phosphat. Nature (London) 1959; 184: 1863
   Web of Science ®Google Scholar
• Pelavin M., Hendrickson D. N., Hollander J. M., Jolly W. L. Phosphorus 2p electron binding energies. Correlation with extended Hückel charge. J. Phys. Chem. 1970; 74: 1116
   Google Scholar
• Dent C. E. A study of the behaviour of some sixty amino-acids and other ninhydrin-reacting substances on phenol-‘collidine’ filter-paper chromatograms, with note. Biochem. J. 1948; 43: 169
   Web of Science ®Google Scholar
• Zajac J. Separation of phosphate esters of ethanolamine, serine, and threonine using chromatography and paper electrophoresi. Chem. Anal. (Warsaw) 1962; 7: 995
   Google Scholar
• Fink K., Cline R. E., Fink R. M. Paper chromatography of several classes of compounds: Correlated Rf values in a variety of solvent system. Anal. Chem. 1963; 35: 389
   Web of Science ®Google Scholar
• Shkolnik R. Ya., Doman N. G., Lobas I. G. Additional data on the chromatographic separation of products of metabolism into fractions (Russ.. Biokhimiya 1965; 30: 265
   PubMedGoogle Scholar
• Reio L. Third supplement for the paper chromatographic separation and identification of phenol derivatives and related compounds of biochemical interest using a “reference system”. J. Chromatogr. 1970; 47: 60
   PubMed Web of Science ®Google Scholar
• Schumacher G., Sandermann H., Jr. Solubility of phospholipid polar group model compounds in wate. Biochim. Biophys. Acta 1976; 448: 642
   PubMed Web of Science ®Google Scholar
• Fahn S., Albers R. W., Kowal G. J. Thin-layer chromatography for the separation of nucleotide. Anal. Biochem. 1965; 10: 468
   Web of Science ®Google Scholar
• Chiari D., Roehr M., Widtmann G. Cellulose powders for the determination of amino acids by thin-layer chromatograph. Mikrokhim. Ichnoanal. Acta 1965; 669
   Google Scholar
• Wober W., Thiele O. W. Trennung phosphorhaltiger Abbauprodukte von Phosphatiden auf Celluloseplatte. Biochim. Biophys. Acta 1966; 116: 163
   PubMed Web of Science ®Google Scholar
• Manai M., Cozzone A. J. Two-dimensional separation of phosphoamino acids from nucleoside monophosphate. Anal. Biochem. 1982; 124: 12
   PubMed Web of Science ®Google Scholar
• Wälinder O. Identification and isolation of 1-32P-phosphohistidine, 3-32P-phosphohistidine, and N°-32P-phospholysine from erythrocytic nucleoside diphosphate kinase, incubated with adenosine triphosphate-32. J. Biol. Chem. 1968; 243: 3947
   PubMed Web of Science ®Google Scholar
• Kennedy E. P., Smith S. W. The isolation of radioactive phosphoserine from “phosphoprotein” of the Ehrlich ascites tumo. J. Biol. Chem. 1954; 207: 153
   PubMed Web of Science ®Google Scholar
• Moore S., Stein W. H. Procedures for the chromatographic determination of amino acids on four per cent cross-linked sulfonated polystyrene resin. J. Biol. Chem. 1954; 211: 893
   PubMed Web of Science ®Google Scholar
• Schormüller J., Belitz H.-D., Lehmann K. Über die Trennung und quantitative Bestimmung von Phosphoserin, Phosphothreonin, Serin und Threoni. Z. Lebensm.-Untersuch. u -Forsch. 1957; 105: 474
   Google Scholar
• Spackman D. H., Stein W. H., Moore S. Automatic recording apparatus for use in the chromatography of amino acid. Anal. Chem. 1958; 30: 1190
   Web of Science ®Google Scholar
• Strid L. Separation of some O-phosphorylated amino acids and peptides on anion exchange resi. Acta Chem. Scand. 1959; 13: 1787
   Google Scholar
• Hamilton P. B. Ion exchange chromatography of amino acids. A single column, high resolving, fully automatic procedur. Anal. Chem. 1963; 35: 2055
   Web of Science ®Google Scholar
• Weinstein L. H., Bozarth R. F., Porter C. A., Mandl R. H., Tweedy B. G. Automated analysis of phosphorus containing compounds in biological materials. I. A quantitative procedur. Contrib. Boyce Thompson Inst. 1964; 22: 389
   Google Scholar
• DeMarco C., Coletta M., Cavallini D. Column chromatography of phosphoserine, phospho-ethanolamine and S-sulfoglutathione and their identification in the presence of other acidic amino acid. J. Chromatogr. 1965; 20: 500
   PubMed Web of Science ®Google Scholar
• Borner K. Analysis of amino acids by column chromatography with anion exchangers (Germ.. Z. Klin. Chem. 1966; 4: 212
   Google Scholar
• Kurahashi K., Abood L. G., Gombos G. Ion exchange chromatography of some acidic and aromatic amino acid. J. Chromatogr. 1966; 24: 264
   PubMed Web of Science ®Google Scholar
• Niece R. L. Automated single-column analysis of amino acids using ascorbic acid as reductant for air-stable ninhydri. J. Chromatogr. 1975; 103: 25
   PubMed Web of Science ®Google Scholar
• Kinnier W. J., Wilson J. E. Complete analysis of protein hydrolysates containing phosphoserine and phosphothreonine using the amino acid analyze. J. Chromatogr. 1977; 135: 508
   PubMed Web of Science ®Google Scholar
• Egly J. M., Porath J. Charge-transfer and water-mediated chromatography. II. Adsorption of nucleotide and related compounds on acriflavin-Sephade. J. Chromatogr. 1979; 168: 35
   Web of Science ®Google Scholar
• Werum L. N., Gordon H. T., Thornburg W. Rapid paper ionophoresis using organic buffers in water-formamide and water-ure. J. Chromatogr. 1960; 3: 125
   Web of Science ®Google Scholar
• Sanecka-Obacz M., Sacharuk M., Radwan P. Simple method for detecting phosphoserine and phosphothreonine in proteins (Pol.. Ann. Univ. Mariae Curie-Sklodowska 1979; 34D: 47
   Google Scholar
• Makitie O., Mirttinen S. Acid strengths of some esters of orthophosphoric aci. Suom. Kemistilehti 1971; 44B: 155
   Google Scholar
• Verbert A., Nowogrocki G., Wozniak M. Determination des constantes d'acidite de diacides moyennement fort. Talanta 1980; 27: 436
   PubMedGoogle Scholar
• Laboratoires Sobio S. A. 1968, N-Phosphoryl Aspartic Acid Salts for Treating Psychic and Physic Asthenia, French Patent M6430
   Google Scholar
• Koboshi S. Processing of Silver Halide Color Photographic Material. Japanese Patent 1979; 161: 932
   Google Scholar
• Boissier J. R., Combes G. A. Sels Organo-Phosphoriques de Calciu. French Patent M3196 1965
   Google Scholar
• Köhler F. Arzneimittel zur therapeutischen Verwendung in der Dermatologie und Chirurgi. German Patent 2,216,000 1973
   Google Scholar
• Mouries C., Vangien B., Prat G., Pontagnier H. Diisopropylamine Salts with Activity with Respect to the Central Nervous Syste. French Patent 2 1981; 461: 725
   Google Scholar
• Gresh N., Pullman B. A theoretical study of the binding of sodium to serine phosphate, presented at the Int. Symp. Biomolec. Structur. Conformation, Function and Evolution, Madras, Jan. 4 to 7, 1978, 575
   Google Scholar
• Fioretti M. Sullacido etilendiammino tetracetico ed alcuni sali di interesse farmaceutic. Ann. Chim. (Rome) 1963; 53: 1161
   Google Scholar
• Pietrogrande A., Dalla Fini G. Microdetermination of carbon-hydrogen in organic derivatives of phosphoric acid (Ital.. Atti Ist Veneto Sci., Lett. Arti, Cl. Sci. Mat. Nat. 1976; 134: 189
   Google Scholar