D-amino acids in nature, agriculture and biomedicine

References

• Arakawa N, Igarashi M, Kazuoka T, Oikawa T, Soda K. 2003. D-arginase of Arthrobacter sp. KUJ 8602: characterization and its identity with Zn(2+)-guanidinobutyrase. J Biochem. 133(1):33–42. https://doi.org/https://doi.org/10.1093/jb/mvg016.
   PubMed Web of Science ®Google Scholar
• Ariyoshi M, Katane M, Hamase K, Miyoshi Y, Nakane M, Hoshino A, Okawa Y, Mita Y, Kaimoto S, Uchihashi M, et al. 2017. D-Glutamate is metabolized in the heart mitochondria. Sci Rep. 7:43911. doi:https://doi.org/10.1038/srep43911.
   PubMed Web of Science ®Google Scholar
• Bai L, Livnat I, Romanova EV, Alexeeva V, Yau PM, Vilim FS, Weiss KR, Jing J, Sweedler JV. 2013. Characterization of GdFFD, a D-amino acid-containing neuropeptide that functions as an extrinsic modulator of the Aplysia feeding circuit. J Biol Chem. 288(46):32837–32851. doi:https://doi.org/10.1074/jbc.M113.486670.
   PubMed Web of Science ®Google Scholar
• Bailey JM. 1998. RNA-directed amino acid homochirality. FASEB J. 12:503–507. https://doi.org/https://doi.org/10.1096/fasebj.12.6.503.
   PubMedGoogle Scholar
• Baker DH. 2006. Comparative species utilization and toxicity of sulfur amino acids. J Nutr. 136(6):1670S–1675S. doi:https://doi.org/10.1093/jn/136.6.1670S.
   PubMed Web of Science ®Google Scholar
• Balasubramanian R. 1983. Possible mechanism for origin of chiral specificity during origins of life. Orig Life. 13:109–112. https://doi.org/https://doi.org/10.1007/BF00928888.
   PubMedGoogle Scholar
• Baldassarre M, Scirè A, Fiume I, Tanfani F. 2011. Insights into the structural properties of D-serine dehydratase from Saccharomyces cerevisiae: an FT-IR spectroscopic and in silico approach. Biochimie. 93:542–548. doi:https://doi.org/10.1016/j.biochi.2010.11.009.
   PubMed Web of Science ®Google Scholar
• Bardaweel SK, Abu-Dahab R, Almomani NF. 2013. An in vitro based investigation into the cytotoxic effects of D-amino acids. Acta Pharm. 63(4):467–478. doi:https://doi.org/10.2478/acph-2013-0032.
   PubMed Web of Science ®Google Scholar
• Bhagavan NV, Ha C-E. 2015. Essentials of medical biochemistry: with clinical cases. 2nd ed. USA: Academic Press. p. 752.
   Google Scholar
• Bouillaut L, Self WT, Sonenshein AL. 2013. Proline-dependent regulation of Clostridium difficile Stickland metabolism. J Bacteriol. 195(4):844–854. doi:https://doi.org/10.1128/JB.01492-12.
   PubMed Web of Science ®Google Scholar
• Boza JJ, Martínez-Augustin O, Baró L, Suarez MD, Gil A. 1995. Protein v. enzymic protein hydrolysates. nitrogen utilization in starved rats. Br J Nutr. 73(1):65–71. https://doi.org/https://doi.org/10.1079/BJN19950009.
   PubMed Web of Science ®Google Scholar
• Brückner H, Westhauser T. 2003. Chromatographic determination of L- and D-amino acids in plants. Amino Acids. 24:43–55. https://doi.org/https://doi.org/10.1007/s00726-002-0322-8.
   PubMed Web of Science ®Google Scholar
• Cartus AT. 2012. D-Amino acids and cross-linked amino acids as food contaminants. In: Schrenk D, editor. Chemical contaminants and residues in food. Cambridge: Woodhead Publishing; p. 286–319. doi:https://doi.org/10.1533/9780857095794.2.286.
   Google Scholar
• Checco JW, Zhang G, Yuan WD, Yu K, Yin SY, Roberts-Galbraith RH, Yau PM, Romanova EV, Jing J, Sweedler JV. 2018. Molecular and physiological characterization of a receptor for D-amino acid-containing neuropeptides. ACS Chem Biol. 13(5):1343–1352. doi:https://doi.org/10.1021/acschembio.8b00167.
   PubMed Web of Science ®Google Scholar
• Cherkin A, Davis JL, Garman MW. 1978. D-Proline: stereospecificity and sodium chloride dependence of lethal convulsant activity in the chick. Pharmacol Biochem Behav. 8(5):623–625. https://doi.org/https://doi.org/10.1016/0091-3057(78)90399-4.
   PubMed Web of Science ®Google Scholar
• Chernobrovkin MG, Anan’eva IA, Shapovalova EN, Shpigun OA. 2004. Determination of amino acid enantiomers in pharmaceuticals by reversed-phase high-performance liquid chromatography. J Anal Chem. 59(1):55–63. https://doi.org/https://doi.org/10.1023/B:JANC.0000011669.08932.d8.
   Web of Science ®Google Scholar
• Chervyakov AV, Gulyaeva NV, Zakharova MN. 2011. D-amino acids in normal ageing and pathogenesis of neurodegenerative diseases. Neurochemical Journal. 5(2):100–114. https://doi.org/https://doi.org/10.1134/S1819712411020036.
   Web of Science ®Google Scholar
• Chung JS, Zmora N, Katayama H, Tsutsui N. 2010. Crustacean hyperglycemic hormone (CHH) neuropeptidesfamily: functions, titer, and binding to target tissues. Gen Comp Endocrinol. 166(3):447–454. doi:https://doi.org/10.1016/j.ygcen.2009.12.011.
   PubMed Web of Science ®Google Scholar
• Cronin JR, Pizzarello S. 1997. Enantiomeric excesses in meteoritic amino acids. Science. 275(5302):951–955. doi:https://doi.org/10.1126/science.275.5302.951.
   PubMed Web of Science ®Google Scholar
• Csapo J, Albert C, Csapo-Kiss Z. 2009. The D-amino acid content of foodstuffs (A review). Acta Univ Sapientiae, Alimentaria. 2:5–30. http://www.acta.sapientia.ro/acta-alim/C2-1/alim2-1.pdf.
   Google Scholar
• Da Silva JJRF, Da Silva JAL. 2009. D-Amino acids in biology – more than one thinks, (D-amino acidos em biologia – mais do que se julga). Quim Nova. 32:554–561. https://doi.org/http://doi.org/10.1590/S0100-40422009000200046).
   Web of Science ®Google Scholar
• D’Mello JPF. 2003. Amino acids as multifunctional molecules. In: D’Mello JPF, editor. Amino acids in animal nutrition. 2nd ed. CABI Publishing; p. 1–14. doi:https://doi.org/10.1079/9780851996547.0001.
   Google Scholar
• Elsila JE, Aponte JC, Blackmond DG, Burton AS, Dworkin JP, Glavin DP. 2016. Meteoritic amino acids: diversity in compositions reflects parent body histories. ACS Cent Sci. 2(6):370–379. doi:https://doi.org/10.1021/acscentsci.6b00074.
   PubMed Web of Science ®Google Scholar
• Englander MT, Avins JL, Fleisher RC, Liu B, Effraim PR, Wang J, Schulten K, Leyh TS, Jr GR, Cornish VW. 2015. The ribosome can discriminate the chirality of amino acids within its peptidyl-transferase center. PNAS. 112(19):6038–6043. doi:https://doi.org/10.1073/pnas.1424712112.
   PubMed Web of Science ®Google Scholar
• Errico F, Mothet JP, Usiello A. 2015. D-Aspartate: an endogenous NMDA receptor agonist enriched in the developing brain with potential involvement in schizophrenia. J Pharm Biomed Anal. 116:7–17. doi:https://doi.org/10.1016/j.jpba.2015.03.024.
   PubMed Web of Science ®Google Scholar
• Errico F, Nisticò R, Napolitano F, Mazzola C, Astone D, Pisapia T, Giustizieri M, D’Aniello A, Mercuri NB, Usiello A. 2011. Increased D-aspartate brain content rescues hippocampal age-related synaptic plasticity deterioration of mice. Neurobiol Aging. 32(12):2229–2243. doi:https://doi.org/10.1016/j.neurobiolaging.2010.01.002.
   PubMed Web of Science ®Google Scholar
• Errico F, Nisticò R, Palma G, Federici M, Affuso A, Brilli E, Topo E, Centonze D, Bernardi G, Bozzi Y, et al. 2008. Increased levels of D-aspartate in the hippocampus enhance LTP but do not facilitate cognitive flexibility. Mol Cell Neurosci. 37(2):236–246. doi:https://doi.org/10.1016/j.mcn.2007.09.012.
   PubMed Web of Science ®Google Scholar
• Fairclough PD, Hegarty JE, Silk DB, Clark ML. 1980. Comparison of the absorption of two protein hydrolysates and their effects on water and electrolyte movements in the human jejunum. Gut. 21(10):829–834. https://gut.bmj.com/content/gutjnl/21/10/829.full.pdf.
   PubMed Web of Science ®Google Scholar
• Falanga A, Nigro E, De Biasi MG, Daniele A, Morelli G, Galdiero S, Scudiero O. 2017. Cyclic peptides as novel therapeutic microbicides: engineering of human defensin mimetics. Molecules. 22(7):E1217. doi:https://doi.org/10.3390/molecules22071217.
   PubMed Web of Science ®Google Scholar
• Fisun OI, Savin AV. 1992. Homochirality and long-range transfer in biological systems. Biosystems. 27(3):129–135. https://doi.org/https://doi.org/10.1016/0303-2647(92)90068-A.
   PubMed Web of Science ®Google Scholar
• Freeman HJ, Sleisinger MH, Kim YS. 1983. Human protein digestion and absorption: normal mechanisms and protein-energy malnutrition. Clin Gastroenterol. 12(2):357–378. https://www.ncbi.nlm.nih.gov/pubmed/6409468.
   PubMedGoogle Scholar
• Fujii N. 2005. D-amino acid in elderly tissues. Biol Pharm Bull. 28(9):1585–1589. https://doi.org/https://doi.org/10.1248/bpb.28.1585.
   PubMed Web of Science ®Google Scholar
• Fujii N, Saito T. 2004. Homochirality and life. Chem Rec. 4:267–278. doi:https://doi.org/10.1002/tcr.20020.
   PubMed Web of Science ®Google Scholar
• Fujii N, Takata Т, Fujii N, Aki K, Sakaue H. 2018. D-Amino acids in protein: the mirror of life as a molecular index of aging. Biochim Biophys Acta. 1866(7):840–847. doi:https://doi.org/10.1016/j.bbapap.2018.03.001.
   Web of Science ®Google Scholar
• Gandolfi I, Palla G, Marchelli R, Dossena A, Puelli S, Salvadori C. 1994. D-Alanine in fruit juices: a molecular marker of bacterial activity, heat treatments and shelf-life. J Food Sci. 59(1):152–154. https://doi.org/https://doi.org/10.1111/j.1365-2621.1994.tb06921.x.
   Web of Science ®Google Scholar
• Gholizadeh A. 2015. The possible involvement of D-amino acids or their metabolites in Arabidopsis cysteine proteinase/cystatin N-dependent proteolytic pathway. Tsitol Genet. 49(2):73–79. https://doi.org/https://doi.org/10.3103/S0095452715020036.
   Google Scholar
• Gogami Y, Ito K, Kamitani Y, Matsushima Y, Oikawa T. 2009. Occurrence of D-serine in rice and characterization of rice serine racemase. Phytochemistry. 70(3):380–387. doi:https://doi.org/10.1016/j.phytochem.2009.01.003.
   PubMed Web of Science ®Google Scholar
• Grimble GK, Keohane PP, Higgins BE, Kaminski MV Jr., Silk DB. 1986. Effect of peptide chain length on amino acid and nitrogen absorption from two lactalbumin hydrolysates in the normal human jejunum. Clin Sci. 71(1): 65–69. doi:https://doi.org/10.1042/cs0710065.
   PubMed Web of Science ®Google Scholar
• Grishin DV, Gladilina YA, Aleksandrova SS, Pokrovskaya MV, Podobed OV, Pokrovskii VS, Zhdanov DD, Sokolov NN. 2017. Creation of thermostable polypeptide cassettes for amino acid balancing in farm animal rations. Appl Biochem Microbiol. 53(6):688–698. https://doi.org/https://doi.org/10.1134/S0003683817060072.
   Web of Science ®Google Scholar
• Grishin DV, Sokolov NN. 2014. Defensins are natural peptide antibiotics of higher eukaryotes. Biochemistry (Moscow) Supplement Series B: Biomedical Chemistry. 8(1):11–18. https://doi.org/https://doi.org/10.1134/S1990750814010077.
   Google Scholar
• Grishin DV, Zhdanov DD, Gladilina J, Pokrovsky VS, Podobed OV, Pokrovskaya MV, Aleksandrova SS, Milyushkina AL, Vigovskiy MA, Sokolov NN. 2018. Construction and Characterization of a Recombinant Mutant Homolog of the CheW protein from Thermotoga petrophila RKU-1. Biochem (Moscow) Suppl S B Biomed Chem. 12(2):143–150. https://doi.org/https://doi.org/10.1134/S1990750818020051.
   Google Scholar
• Hamase K, Morikawa A, Etoh S, Tojo Y, Miyoshi Y, Zaitsu K. 2009. Analysis of small amounts of D-amino acids and the study of their physiological functions in mammals. Anal Sci. 25(8):961–968. https://doi.org/https://doi.org/10.2116/analsci.25.961.
   PubMed Web of Science ®Google Scholar
• Heck SD, Siok CJ, Krapcho KJ, Kelbaugh PR, Thadeio PF, Welch MJ, Williams RD, Ganong AH, Kelly ME, Lanzetti AJ, et al. 1994. Functional consequences of posttranslational isomerization of Ser46 in a calcium channel toxin. Science. 266(5187):1065–1068. doi:https://doi.org/10.1126/science.7973665.
   PubMed Web of Science ®Google Scholar
• Hener C, Hummel S, Suarez J, Stahl M, Kolukisaoglu Ü. 2018. D-Amino acids Are Exuded by Arabidopsis thaliana roots to the Rhizosphere. Int J Mol Sci. 19(4):E1109. doi:https://doi.org/10.3390/ijms19041109.
   PubMed Web of Science ®Google Scholar
• Herrero M, Ibáñez E, Fanali S, Cifuentes A. 2007. Quantitation of chiral amino acids from microalgae by MEKC and LIF detection. Electrophoresis. 28(15):2701–2709. doi:https://doi.org/10.1002/elps.200600599.
   PubMed Web of Science ®Google Scholar
• Horio M, Kohno M, Fujita Y, Ishima T, Inoue R, Mori H, Hashimoto K. 2011. Levels of D-serine in the brain and peripheral organs of serine racemase (Srr) knock-out mice. Neurochem Int. 59(6):853–859. doi:https://doi.org/10.1016/j.neuint.2011.08.017.
   PubMed Web of Science ®Google Scholar
• Jack RW, Jung G. 1998. Natural peptides with antimicrobial activity. Chimia. 52:48–55. http://www.ingentaconnect.com/contentone/scs/chimia/1998/00000052/f0020001/art00006?crawler=true.
   Web of Science ®Google Scholar
• Jenkinson CP, Grody WW, Cederbaum SD. 1996. Comparative properties of arginases. Comp Biochem Physiol B Biochem Mol Biol. 114(1):107–132. https://doi.org/https://doi.org/10.1016/0305-0491(95)02138-8.
   PubMed Web of Science ®Google Scholar
• Jilek A, Mollay C, Tippelt C, Grassi J, Mignogna G, Müllegger J, Sander V, Fehrer C, Barra D, Kreil G. 2005. Biosynthesis of a D-amino acid in peptide linkage by an enzyme from frog skin secretions. PNAS. 102(12):4235–4239. doi:https://doi.org/10.1073/pnas.0500789102.
   PubMed Web of Science ®Google Scholar
• Jimenez EC, Watkins M, Juszczak LJ, Cruz LJ, Olivera BM. 2001. Contryphans from Conus textile venom ducts. Toxicon. 39(6):803–808. https://doi.org/https://doi.org/10.1016/S0041-0101(00)00210-5.
   PubMed Web of Science ®Google Scholar
• Jones H, Venables WA. 1983. Effects of solubilisation on some properties of the membrane-bound respiratory enzyme D-amino acid dehydrogenase of Escherichia coli. FEBS Lett. 151(2):189–192. https://www.ncbi.nlm.nih.gov/pubmed/6131836.
   PubMed Web of Science ®Google Scholar
• Joyce G. 1989. RNA evolution and the origins of life. Nature. 338:217–224. doi:https://doi.org/10.1038/338217a0.
   PubMed Web of Science ®Google Scholar
• Jung E, Kim J, Kim M, Jung DH, Rhee H, Shin JM, Choi K, Kang SK, Kim MK, Yun CH, et al. 2007. Artificial neural network models for prediction of intestinal permeability of oligopeptides. BMC Bioinformatics. 8:1–9. doi:https://doi.org/10.1186/1471-2105-8-245.
   PubMed Web of Science ®Google Scholar
• Kaji Y, Oshika T, Takazawa Y, Fukayama M, Fujii N. 2010. Pathological role of D-amino acid-containing proteins and advanced glycation end products in the development of age-related macular degeneration. Anti-Aging Med. 7(10):107–111. https://doi.org/https://doi.org/10.3793/jaam.7.107.
   Google Scholar
• Keating JJ, Bhattacharya S, Belfort G. 2018. Separation of D, L-amino acids using ligand exchange membranes. J Membr Sci. 555:30–37. https://doi.org/https://doi.org/10.1016/j.memsci.2018.03.030.
   Web of Science ®Google Scholar
• Kuncha SK, Mazeed M, Singh R, Kattula B, Routh SB, Sankaranarayanan R. 2018. A chiral selectivity relaxed paralog of DTD for proofreading tRNA mischarging in Animalia. Nat Commun. 9(1):511. doi:https://doi.org/10.1038/s41467-017-02204-w.
   PubMedGoogle Scholar
• Lin C-H, Yang H-T, Chiu C-C, Lane H-Y. 2017. Blood levels of D-amino acid oxidase vs. D-amino acids in reflecting cognitive aging. Sci Rep. 7:14849. https://doi.org/https://doi.org/10.1038/s41598-017-13951-7.
   PubMed Web of Science ®Google Scholar
• Lins RD, Ferreira R. 2006. The stability of right- and left-handed alpha-helices as a function of monomer chirality. Quim Nova. 29(5):997–998. https://doi.org/http://doi.org/10.1590/S0100-40422006000500020.
   Web of Science ®Google Scholar
• Liu Y, Wang X, Wu H, Chen S, Zhu H, Zhang J, Hou Y, Hu CA, Zhang G. 2016. Glycine enhances muscle protein mass associated with maintaining Akt-mTOR-FOXO1 signaling and suppressing TLR4 and NOD2 signaling in piglets challenged with LPS. Am J Physiol Regul Integr Comp Physiol. 311(2):R365–R373. doi:https://doi.org/10.1152/ajpregu.00043.2016.
   PubMed Web of Science ®Google Scholar
• Maheshwari S. 2013. Environmental impacts of poultry production. Poult Fish Wildl Sci. 1:101. doi:https://doi.org/10.4172/pfw.1000101.
   Google Scholar
• Martínez-Rodríguez S, Martínez-Gómez AI, Rodríguez-Vico F, Clemente-Jiménez JM, Las Heras-Vázquez FJ. 2010. Natural occurrence and industrial applications of D-amino acids: an overview. Chem Biodivers. 7(6):1531–1548. doi:https://doi.org/10.1002/cbdv.200900245.
   PubMed Web of Science ®Google Scholar
• Mignogna G, Simmaco M, Barra D. 1998. Occurrence and function of D-amino acid-containing peptides and proteins: antimicrobial peptides. EXS. 85:29–36. https://www.ncbi.nlm.nih.gov/pubmed/9949866.
   PubMedGoogle Scholar
• Miyamoto T, Homma H. 2018. Detection and quantification of d -amino acid residues in peptides and proteins using acid hydrolysis. BBA Proteins Proteom. 1866(7):775–782. doi:https://doi.org/10.1016/j.bbapap.2017.12.010.
   PubMed Web of Science ®Google Scholar
• Murayama C, Harada N, Kakiuchi T, Fukumoto D, Kamijo A, Kawaguchi AT, Tsukada H. 2009. Evaluation of D-18F-FMT, 18F-FDG, L-11C-MET, and 18F-FLT for monitoring the response of tumors to radiotherapy in mice. J Nucl Med. 50(2):290–295. doi:https://doi.org/10.2967/jnumed.108.057091.
   PubMed Web of Science ®Google Scholar
• Murkin AS, Tanner ME. 2002. Dehydroalanine-based inhibition of a peptide epimerase from spider venom. J Org Chem. 67(24):8389–8394. doi:https://doi.org/10.1021/jo0204653.
   PubMed Web of Science ®Google Scholar
• Mutaguchi Y, Ohmori T, Akano H, Doi K, Ohshima T. 2013. Distribution of D-amino acids in vinegars and involvement of lactic acid bacteria in the production of D-amino acids. Springerplus. 2:691. doi:https://doi.org/10.1186/2193-1801-2-691.
   PubMed Web of Science ®Google Scholar
• Nakatani S, Hidaka K, Ami E, Nakahara K, Sato A, Nguyen JT, Hamada Y, Hori Y, Ohnishi N, Nagai A, et al. 2008. Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV. J Med Chem. 51(10):2992–3004. doi:https://doi.org/10.1021/jm701555p.
   PubMed Web of Science ®Google Scholar
• Negri L, Lattanzi R, Giannini E, Colucci MA, Mignogna G, Barra D, Grohovaz F, Codazzi F, Kaiser A, Kreil G, Melchiorri P. 2005. Biological activities of Bv8 analogues. Br J Pharmacol. 146(5):625–632. doi:https://doi.org/10.1038/sj.bjp.0706376.
   PubMed Web of Science ®Google Scholar
• Owen SM, Rudolph D, Wang W, Cole AM, Sherman MA, Waring AJ, Lehrer RI, Lal RB. 2004. A theta-defensin composed exclusively of D-amino acids is active against HIV-1. J Pept Res. 63(6):469–476. doi:https://doi.org/10.1111/j.1399-3011.2004.00155.x.
   PubMedGoogle Scholar
• Persia ME, Parsons CM, Baker DH. 2003. Amelioration of oral copper toxicity in chicks by dietary additions of ascorbic acid, cysteine and zinc. Nutr Res. 23:1709–1718. https://eurekamag.com/pdf/004/004034268.pdf.
   Web of Science ®Google Scholar
• Peypoux F, Marion D, Maget-Dana R, Ptak M, Das BC, Michel G. 1985. Structure of bacillomycin F, a new peptidolipid antibiotic of the iturin group. Eur J Biochem. 153(2):335–340. https://doi.org/https://doi.org/10.1111/j.1432-1033.1985.tb09307.x.
   PubMedGoogle Scholar
• Pollegioni L, Piubelli L, Sacchi S, Pilone MS, Molla G. 2007. Physiological functions of D-amino acid oxidases: from yeast to humans. CMLS. 64:1373–1394. doi:https://doi.org/10.1007/s00018-007-6558-4.
   PubMed Web of Science ®Google Scholar
• Rekoslavskaya NI. 1986. Possible role of N-malonyl-D-tryptophan as an auxin precursor. Biologia Plantarum. 28:62–67. https://doi.org/https://doi.org/10.1007/BF02885326.
   Web of Science ®Google Scholar
• Rérat A, Vaissade P, Vaugelade P. 1988. Absorption kinetics of dietary hydrolysis products in conscious pigs given diets with different amounts of fish protein 1. Amino-nitrogen and glucose. Br J Nutr. 60:91–104. https://doi.org/https://doi.org/10.1079/BJN19880080.
   PubMed Web of Science ®Google Scholar
• Robbel L, Marahiel MA. 2010. Daptomycin, a bacterial lipopeptide synthesized by a nonribosomal machinery. J Biol Chem. 285(36):27501–27508. doi:https://doi.org/10.1074/jbc.R110.128181.
   PubMed Web of Science ®Google Scholar
• Rojas C, Alt J, Ator NA, Thomas AG, Wu Y, Hin N, Wozniak K, Ferraris D, Rais R, Tsukamoto T, Slusher BS. 2016. D-amino-acid oxidase inhibition increases D-serine plasma levels in mouse but not in monkey or dog. Neuropsychopharmacology. 41(6):1610–1619. doi:https://doi.org/10.1038/npp.2015.319.
   PubMed Web of Science ®Google Scholar
• Silk DB, Fairclough PD, Clark ML, Hegarty JE, Marrs TC, Addison JM, Burston D, Clegg KM, Matthews DM. 1980. Use of a peptide rather than free amino acid nitrogen source in chemically defined “elemental” diets. JPEN J Parenter Enteral Nutr. 4(6):548–553. https://doi.org/https://doi.org/10.1177/0148607180004006548.
   PubMed Web of Science ®Google Scholar
• Silk DBA, Grimble GK, Rees RG. 1985. Protein digestion and amino acid and peptide absorption. Proc Nutr Soc. 44(1):63–72. https://doi.org/https://doi.org/10.1079/PNS19850011.
   PubMed Web of Science ®Google Scholar
• Soares TA, Lins RD, Longo R, Garratt R, Ferreira R. 1997. Plural origins of molecular homochirality in our biota part II. The relative stabilities of homochiral and mixed oligoribotides and peptides. Z. Naturforsch. 52:89–96. http://zfn.mpdl.mpg.de/data/Reihe_C/52/ZNC-1997-52c-0089.pdf.
   Google Scholar
• Sorokina ON, Sumina EG, Shtykov SN, Atayan VZ, Barysheva SV. 2010. TLC separation of D-, L -of amino acids in the 2-hydroxypropyl-ß- cyclodextrin aqueous mobile phase. Sorption and Chromatographic Processes. 10(1):135–141. http://www.sorpchrom.vsu.ru/?l=en&p=6&y=2010&vol=10&num=1 (in Russian)
   Google Scholar
• Soutourina J, Blanquet S, Plateau P. 2001. Role of D-cysteine desulfhydrase in the adaptation of Escherichia coli to D-cysteine. J Biol Chem. 276(44):40864–40872. doi:https://doi.org/10.1074/jbc.M102375200.
   PubMed Web of Science ®Google Scholar
• Soutourina J, Plateau P, Blanquet S. 2000. Metabolism of D-aminoacyl-tRNAs in Escherichia coli and Saccharomyces cerevisiae cells. J Biol Chem. 275(42):32535–32542. doi:https://doi.org/10.1074/jbc.M005166200.
   PubMed Web of Science ®Google Scholar
• Strauch RC, Svedin E, Dilkes B, Chapple C, Li X. 2015. Discovery of a novel amino acid racemase through exploration of natural variation in Arabidopsis thaliana. PNAS. 112(37):11726–11731. doi:https://doi.org/10.1073/pnas.1503272112.
   PubMed Web of Science ®Google Scholar
• Szilágyi B, Kovács P, Ferenczy GG, Rácz A, Németh K, Visy J, Szabó P, Ilas J, Balogh GT, Monostory K, et al. 2018. Discovery of isatin and 1H-indazol-3-ol derivatives as D-amino acid oxidase (DAAO) inhibitors. Bioorg Med Chem. 26(8):1579–1587. doi:https://doi.org/10.1016/j.bmc.2018.02.004.
   PubMed Web of Science ®Google Scholar
• Takayama T, Ogawa T, Hidaka M, Shimizu Y, Ueda T, Masaki H. 2005. Esterification of Escherichia coli tRNAs with D-histidine and D-lysine by aminoacyl-tRNA synthetases. Biosci Biotechnol Biochem. 69(5):1040–1041. doi:https://doi.org/10.1271/bbb.69.1040.
   PubMed Web of Science ®Google Scholar
• Ten Have GA, Engelen MP, Luiking YC, Deutz NE. 2007. Absorption kinetics of amino acids, peptides, and intact proteins. Int J Sport Nutr Exerc Metab. 17:S23–S36. https://pdfs.semanticscholar.org/8344/b4e504ebd0c21a97a495560c6c58dcac795a.pdf.
   PubMed Web of Science ®Google Scholar
• Timofeeva NM, Khavinson VKh, Malinin VV, Nikitina AA, Egorova VV. 2005. Effect of peptide Livagen on activity of digestive enzymes in gastrointestinal tract and non-digestive organs in rats of different ages. Adv Gerontol. 16:92–96. https://www.ncbi.nlm.nih.gov/pubmed/16075683 (in Russian).
   PubMedGoogle Scholar
• Torbeev VY, Raghuraman H, Hamelberg D, Tonelli M, Westler WM, Perozo E, Kent SB. 2011. Protein conformational dynamics in the mechanism of HIV-1 protease catalysis. PNAS. 108(52):20982–20987. doi:https://doi.org/10.1073/pnas.1111202108.
   PubMed Web of Science ®Google Scholar
• Torres AM, Menz I, Alewood PF, Bansal P, Lahnstein J, Gallagher CH, Kuchel PW. 2002. D-Amino acid residue in the C-type natriuretic peptide from the venom of the mammal, Ornithorhynchus anatinus, the Australian platypus. FEBS Lett. 524(1–3):172–176. https://doi.org/https://doi.org/10.1016/S0014-5793(02)03050-8.
   PubMed Web of Science ®Google Scholar
• Torres AM, Tsampazi M, Kennett EC, Belov K, Geraghty DP, Bansal PS, Alewood PF, Kuchel PW. 2007. Characterization and isolation of L-to-D-amino-acid-residue isomerase from platypus venom. Amino Acids. 32(1):63–68. doi:https://doi.org/10.1007/s00726-006-0346-6.
   PubMed Web of Science ®Google Scholar
• Tutel’yan VA, Khavinson V, Malinin VV. 2003. Physiological role of short peptides in nutrition. Bull Exp Biol Med. 135(1):1–5. https://doi.org/https://doi.org/10.1023/A:1023467622252.
   PubMed Web of Science ®Google Scholar
• Tverdislov VA, Yakovenko LV. 2008. Physical aspects of the emergence of living cell precursors: the ion and chiral asymmetries as two fundamental asymmetry types. Mosc Univ Phys Bull. 63:151–163. https://doi.org/https://doi.org/10.3103/S0027134908030016.
   Web of Science ®Google Scholar
• Urakami T, Sakai K, Asai T, Fukumoto D, Tsukada H, Oku N. 2009. Evaluation of O-[18F]fluoromethyl-d-tyrosine as a radiotracer for tumor imaging with positron emission tomography. Nucl Med Biol. 36(3):295–303. doi:https://doi.org/10.1016/j.nucmedbio.2008.12.012.
   PubMed Web of Science ®Google Scholar
• Volkmann RA, Heck SD. 1998. Biosynthesis of D-amino acid-containing peptides: exploring the role of peptide isomerases. EXS. 85:87–105. https://www.ncbi.nlm.nih.gov/pubmed/9949870.
   PubMedGoogle Scholar
• Wang G. 2012. Natural antimicrobial peptides as promising anti-HIV candidates. Curr Top Pept Protein Res. 13:93–110. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4730921/pdf/nihms727000.pdf.
   PubMedGoogle Scholar
• Whittington CM, Koh JM, Warren WC, Papenfuss AT, Torres AM, Kuchel PW, Belov K. 2009. Understanding and utilising mammalian venom via a platypus venom transcriptome. J Proteomics. 72(2):155–164. doi:https://doi.org/10.1016/j.jprot.2008.12.004.
   PubMed Web of Science ®Google Scholar
• Wolosker H. 2007. NMDA receptor regulation by D-serine: New findings and perspectives. Mol Neurobiol. 36(2): 152–164. doi:https://doi.org/10.1007/s12035-007-0038-6.
   PubMed Web of Science ®Google Scholar
• Wolosker H, Dumin E, Balan L, Foltyn VN. 2008. D-amino acids in the brain: D-serine in neurotransmission and neurodegeneration. FEBS J. 275(14):3514–3526. doi:https://doi.org/10.1111/j.1742-4658.2008.06515.x.
   PubMed Web of Science ®Google Scholar
• Yokoyama T, Kan-no N, Ogata T, Kotaki Y, Sato M, Nagahisa E. 2003. Presence of free D-amino acids in microalgae. Biosci Biotechnol Biochem. 67(2):388–392. https://doi.org/https://doi.org/10.1271/bbb.67.388.
   PubMed Web of Science ®Google Scholar
• Yu P, Hegeman AD, Cohen JD. 2014. A facile means for the identification of indolic compounds from plant tissues. Plant J. 79(6):1065–1075. doi:https://doi.org/10.1111/tpj.12607.
   PubMed Web of Science ®Google Scholar