Synthesis of Carnosine-d₇ and Anserine-d₄ for Use as Internal Standards in Liquid Chromatography–Mass Spectrometry

REFERENCES

• Boldyrev , A. A. ; Severin , S. E. The histidine-containing dipeptides, carnosine and anserine: Distribution, properties, and biological significance . Adv. Enzy. Regul. 1990 , 30 , 175 – 194 .
   PubMedGoogle Scholar
• Quinn , P. J. ; Boldyrev , A. A. ; Formazuyk , V. E. Carnosine: Its properties, functions, and potential therapeutic applications . Mol. Aspects Med. 1992 , 13 , 379 – 444 .
   PubMed Web of Science ®Google Scholar
• Gulewitsch , W. ; Amiradzibi , S. Ueber das Carnosin, eine neue organische Base des Fleischextractes . Ber. Deutsch. Chem. Ges. 1900 , 33 , 1902 – 1903 .
   Google Scholar
• Ackermann , D. ; Timpe , O. ; Poller , K. Uber das Anserin, einen neuen Bestandteil der Vogelmuskulatur . Physiol. Chem. 1929 , 183 , 1 – 10 .
   Google Scholar
• Kohen , R. ; Yamamoto , Y. ; Cundy , K. C. ; Ames , B. N. Antioxidant activity of carnosine, homocarnosine, and anserine present in muscle and brain . Proceed. Nat. Acad. Sci. 1988 , 85 , 3175 – 3179 .
   PubMed Web of Science ®Google Scholar
• Aruoma , O. I. ; Laughton , M. J. ; Halliwell , B. Carnosine, homocarnosine, and anserine: Could they act as antioxidants in vivo? Biochem. J. 1989 , 264 , 863 – 869 .
   PubMed Web of Science ®Google Scholar
• Babizhayev , M. A. ; Seguin , M. C. ; Gueyne , J. ; Evstigneeva , R. P. ; Ageyeva , E. A. ; Zheltukhina , G. A. L-Carnosine (β-alanyl-L-histidine) and carcinine (β-alanylhistamine) act as natural antioxidants with hydroxyl-radical-scavenging and lipid-peroxidase activities . Biochem. J. 1994 , 304 (Pt. 2) , 509 – 516 .
   PubMed Web of Science ®Google Scholar
• Fonteh , A. N. ; Harrington , R. J. ; Harrington , M. G. Quantification of free amino acids and dipeptides using isotope dilution liquid chromatography and electrospray ionization tandem mass spectrometry . Amino Acids 2007 , 32 , 203 – 212 .
   PubMed Web of Science ®Google Scholar
• Fonteh , A. N. ; Harrington , R. J. ; Tsai , A. ; Liao , P. ; Harrington , M. G. Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids 2007, 32, 213–224.
   PubMed Web of Science ®Google Scholar
• Stokvis , E. ; Rosing , H. ; Beijnen , J. H. Stable isotopically labeled internal standards in quantitative bioanalysis using liquid chromatography/mass spectrometry: Necessity or not? Rapid Commun. Mass Spectrom. 2005 , 19 , 401 – 407 .
   PubMed Web of Science ®Google Scholar
• Sifferd , R. H. ; du Vigneaud , V. A new synthesis of carnosine, with some observations on the splitting of the benzyl group from carbobenzoxy derivatives and from benzylthio ethers . J. Biol. Chem. 1935 , 108 , 753 – 761 .
   Google Scholar
• Behrens , O. K. ; du Vigneaud , V. The synthesis of anserine from l-1-methylhistidine . J. Biol. Chem. 1937 , 120 , 517 – 522 .
   Google Scholar
• Wiles , C. W. ; Watts , P. An expedient, scalable synthesis of the natural product L-anserine . Synthesis 2007 , 2608 – 2610 .
   Google Scholar
• Dudash Jr. , J. ; Jiang , J. ; Mayer , S. C. ; Joulli , M. M. Comparative study of selected coupling reagents in dipeptide synthesis . Synth. Commun. 1993 , 23 , 349 – 356 .
   Google Scholar
• Dado , G. P. ; Gellman , S. H. Intramolecular hydrogen bonding in derivatives of β-alanine and γ-amino butyric acid: Model studies for the folding of unnatural polypeptide backbones . J. Am. Chem. Soc. 1994 , 116 , 1054 – 1062 .
   Google Scholar
• Biemann , K. Mass Spectrometry: Organic Chemical Applications ; McGraw-Hill : New York , 1962 ; pp. 223 – 224 .
   Google Scholar
• Bradbury , J. H. ; Chapman , B. ; Crompton , M. W. ; Norton , R. ; Teh , J. Hydrogen–deuterium exchange of the C-2 protons of histidine and histidine peptides and proteins . J. Chem. Soc. Perkin Trans. 2 1980 , 693 – 699 .
   Google Scholar