Origin, microbiology, nutrition, and pharmacology of D-amino acids

Chemistry and Biodiversity

Volumn 7, Issue 6, 2010, Pages 1491-1530

  Friedman, Mendel ^a  

^a WESTERN REGIONAL RESEARCH CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIAMINOPROPIONIC ACID; ALANINE; AMINO ACID DECARBOXYLASE; ARGININE; ASPARAGINE; ASPARTIC ACID; CYSTEINE; DEHYDROALANINE; DEXTRO AMINO ACID; DEXTRO PHENYLALANINE; GLUTAMIC ACID; GLUTAMINE; GLYCINE; HISTIDINE; ISOLEUCINE; LANTHIONINE; LEUCINE; LYSINE; LYSINOALANINE; METHIONINE; PHENYLALANINE; PROLINE; SERINE; THREONINE; TRYPTOPHAN; TYROSINE; VALINE; AMINO ACID; ANTIMICROBIAL CATIONIC PEPTIDE; PEPTIDE; PEPTIDOGLYCAN;

AMINO ACID METABOLISM; BIOLOGICAL ACTIVITY; CHIRALITY; CROSS LINKING; CRYSTALLIZATION; FOOD; GROWTH INHIBITION; HUMAN; ISOMER; MICROBIOLOGY; NONHUMAN; NUTRITION; NUTRITIONAL VALUE; PHARMACOLOGY; RACEMIZATION; REVIEW; SAFETY; ANIMAL; BACTERIA; CHEMISTRY; FOOD ANALYSIS; METABOLISM; MOUSE; PLANT; RAT; STEREOISOMERISM; TOXICITY;

ANIMALIA; INVERTEBRATA; MUS; RATTUS;

AMINO ACIDS; ANIMALS; ANTIMICROBIAL CATIONIC PEPTIDES; BACTERIA; FOOD ANALYSIS; HUMANS; LYSINOALANINE; MICE; PEPTIDES; PEPTIDOGLYCAN; PLANTS; RATS; STEREOISOMERISM;

EID: 77953888010     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.200900225     Document Type: Review

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123. M. Friedman, P. R. Henika, C. E. Levin, R. E. Mandrell, 'Antimicrobial wine formulations active against the foodborne pathogens Escherichia coli O157: H7 and Salmonella enterica', J. Food Sci. 2006, 71, M245-M251.
124. M. Friedman, M. R. Gumbmann, 'Dietary significance of D-amino acids', in 'Absorption and Utilization of Amino Acids', Ed. M. Friedman, CRC Press, Boca Raton, FL, 1989, Vol. 2, pp. 173-190.
125. S. Y. Chung, H. E. Swaisgood, G. L. Catignani, 'Effects of alkali treatment and heat treatment in the presence of fructose on digestibility of food proteins as determined by an immobilized digestive enzyme assay (IDEA)', J. Agric. Food Chem. 1986, 34, 579-584.
126. A. P. De Groot, P. Slump, V. J. Feron, L. Van Beek, 'Effects of alkali treated proteins: feeding studies with free and protein bound lysinoalanine in rats and other animals', J. Nutr. 1976, 106, 1527-1538.
127. R. Hayashi, I. Kameda, 'Decreased proteolysis of alkali-treated protein: consequences of racemization in food processing', J. Food Sci. 1980, 45, 1430-1431.
128. P. Slump, 'Lysinoalanine in alkali-treated proteins and factors influencing its biological activity', Ann. Nutr. Aliment. 1978, 32, 271-279.
129. L. Savoie, G. Parent, I. Galibois, 'Effects of alkali treatment on the in-vitro digestibility of proteins and the release of amino acids', J. Sci. Food Agric. 1991, 56, 363-372.
130. L. Savoie, 'Effect of protein treatment on the enzymatic hydrolysis of lysinoalanine and other amino acids', Adv. Exp. Med. Biol. 1984, 177, 413-422.
131. H. E. Swaisgood, G. L. Catignani, 'Digestibility of modified milk proteins: nutritional implications', J. Dairy Sci. 1985, 68, 2782-2790.
132. B. Possompes, J. Berger, 'Effect of severely alkali-treated casein on gastrointestinal transit and selected intestinal enzyme activities', Adv. Exp. Med. Biol. 1986, 199, 517-530.
133. G. Sarwar, A. Paquet, 'Availability of amino acids in some tripeptides and derivatives present in dietary proteins', in 'Absorption and Utilization of Amino Acids', Ed. M. Friedman, CRC Press, Boca Raton, FL, 1989, Vol. 2, pp. 148-154.
134. 15N-tracer technique', Clin. Nutr. 1983, 2, 31-35.
135. R. Hayashi, 'Lysinoalanine as a metal chelator. An implication for toxicity', J. Biol. Chem. 1982, 257, 13896-13898.
136. M. Friedman, O. K. Grosjean, J. C. Zahnley, 'Carboxypeptidase inhibition by alkali-treated food proteins', J. Agric. Food Chem. 1985, 33, 208-213.
137. M. Friedman, O. K. Grosjean, J. C. Zahnley, 'Metalloenzyme inhibition by lysinoalanine, phenylethylaminoalanine, and alkali-treated food proteins', Fed. Proc. 1985, 44, 6351.
138. M. Friedman, O. K. Grosjean, J. C. Zahnley, 'Inactivation of metalloenzymes by food constituents', Food Chem. Toxicol. 1986, 24, 897-902.
139. M. Friedman, O. K. Grosjean, J. C. Zahnley, 'Inactivation of metalloenzymes by lysinoalanine, phenylethylaminoalanine, alkali-treated food proteins, and sulfur amino acids', Adv. Exp. Med. Biol. 1986, 199, 531-560.
140. O. Chacon, L. E. Bermudez, D. K. Zinniel, H. K. Chahal, R. J. Fenton, Z. Feng, K. Hanford, L. G. Adams, R. G. Barletta, 'Impairment of D-alanine biosynthesis in Mycobacterium smegmatis determines decreased intracellular survival in human macrophages', Microbiology (Reading, U.K.) 2009, 155, 1440-1450.
141. K. T. Osman, L. Du, Y. He, Y. Luo, 'Crystal structure of Bacillus cereus D-alanyl carrier protein ligase (DltA) in complex with ATP', J. Mol. Biol. 2009, 388, 345-355.
142. 14C]-amino acids into Chinese hamster ovary (CHO-K1) cells: implications for use of labeled D-amino acids as molecular imaging agents', Nucl. Med. Biol. 2007, 34, 659-665.
143. L. D. Stegman, H. Zheng, E. R. Neal, O. Ben-Yoseph, L. Pollegioni, M. S. Pilone, B. D. Ross, 'Induction of cytotoxic oxidative stress by D-alanine in brain tumor cells expressing Rhodotorula gracilis D-amino acid oxidase: a cancer gene therapy strategy', Hum. Gene Ther. 1998, 9, 185-193.
144. G. E. Tsai, P. Yang, Y.-C. Chang, M.-Y. Chong, 'D-Alanine added to antipsychotics for the treatment of schizophrenia', Biol. Psychiatry 2006, 59, 230-234.
145. A. Morikawa, K. Hamase, Y. Miyoshi, S. Koyanagi, S. Ohdo, K. Zaitsu, 'Circadian changes of D-alanine and related compounds in rats and the effect of restricted feeding on their amounts', J. Chromatogr., B 2008, 875, 168-173.
146. Y. Nagata, M. Higashi, Y. Ishii, H. Sano, M. Tanigawa, K. Nagata, K. Noguchi, M. Urade, 'The presence of high concentrations of free D-amino acids in human saliva', Life Sci. 2006, 78, 1677-1681.
147. A. Suessenbacher, A. Lass, B. Mayer, F. Brunner, 'Antioxidative and myocardial protective effects of L-arginine in oxygen radical-induced injury of isolated perfused rat hearts', Naunyn. Schmiedeberg's Arch. Pharmakol. 2002, 365, 269-276.
148. E. Wiel, Q. Pu, D. Corseaux, E. Robin, R. Bordet, N. Lund, B. Jude, B. Vallet, 'Effect of L-arginine on endothelial injury and hemostasis in rabbit endotoxin shock', J. Appl. Physiol. 2000, 89, 1811-1818.
149. B. Szende, 'The effect of amino acids and amino acid derivatives on cell proliferation', Acta Biomed. Ateneo Parmense 1993, 64, 139-145.
150. E. Navarro, S. J. Alonso, F. A. Martín, M. A. Castellano, 'Toxicological and pharmacological effects of D-arginine', Basic Clin. Pharmacol. Toxicol. 2005, 97, 149-154.
151. H. Koyuncuoǧlu, M. Güngör, Ö. Ang, D. Inanç, M. Ang-Küçüker, H. Saǧduyu, V. Uysal, 'Aggravation by morphine and D-aspartic acid of pyelonephritis induced by i.v. inoculation of Staphylococcus aureus in rats', Infection 1988, 16, 42-45.
152. I. N. Iezhitsa, A. A. Spasov, N. V. Zhuravleva, M. K. Sinolitskii, S. P. Voronin, 'Comparative study of the efficacy of potassium magnesium L-, D- and DL-aspartate stereoisomers in overcoming digoxin- and furosemide-induced potassium and magnesium depletions', Magnesium Res. 2004, 17, 276-292.
153. M. Friedman, M. R. Gumbmann, 'The utilization and safety of isomeric sulfur-containing amino acids in mice', J. Nutr. 1984, 114, 2301-2310.
154. F. W. Benz, D. E. Nerland, W. M. Pierce, C. Babiuk, 'Acute acrylonitrile toxicity: studies on the mechanism of the antidotal effect of D- and L-cysteine and their N-acetyl derivatives in the rat', Toxicol. Appl. Pharmacol. 1990, 102, 142-150.
155. J. Huang, H. Niknahad, S. Khan, P. J. O'Brien, 'Hepatocyte-catalysed detoxification of cyanide by L- and D-cysteine', Biochem. Pharmacol. 1998, 55, 1983-1990.
156. A. E. McLean, G. R. Armstrong, D. Beales, 'Effect of D- or L-methionine and cysteine on the growth inhibitory effects of feeding 1% paracetamol to rats', Biochem. Pharmacol. 1989, 38, 347-352.
157. Y. Takahashi, T. Funakoshi, H. Shimada, S. Kojima, 'Comparative effects of chelating agents on distribution, excretion, and renal toxicity of gold sodium thiomalate in rats', Toxicology 1994, 90, 39-51. (Pubitemid 24193488)
158. M. Friedman, 'The Chemistry and Biochemistry of the Sulfhydryl Group in Amino Acids, Peptides, and Proteins', Permagon Press, Oxford, UK, 1973, 485 pages.
159. M. Friedman, 'Improvement in the safety of foods by SH-containing amino acids and peptides. A review', J. Agric. Food Chem. 1994, 42, 3-20.
160. L. I. Berkeley, J. F. Cohen, D. L. Crankshaw, F. N. Shirota, H. T. Nagasawa, 'Hepatoprotection by L-cysteine-glutathione mixed disulfide, a sulfhydryl-modified prodrug of glutathione', J. Biochem. Mol. Toxicol. 2003, 17, 95-97.
161. B. Todorovic, B. R. Glick, 'The interconversion of ACC deaminase and D-cysteine desulfhydrase by directed mutagenesis', Planta 2008, 229, 193-205.
162. M. S. Masri, M. Friedman, 'Transformation of dehydroalanine to (S)-β-(2-pyridylethyl)-L-cysteine side chains', Biochem. Biophys. Res. Commun. 1982, 104, 321-325.
163. M. Friedman, 'Biological effects of Maillard browning products that may affect acrylamide safety in food', in 'Chemistry and Safety of Acrylamide in Food', Eds. M. Friedman, D. Mottram, Springer, New York, 2005, pp. 135-155.
164. M. Friedman, C. E. Levin, 'Review of methods for the reduction of dietary content and toxicity of acrylamide', J. Agric. Food Chem. 2008, 56, 6113-6140.
165. C. N. Glover, C. Hogstrand, 'Amino acid modulation of in vivo intestinal zinc absorption in freshwater rainbow trout', J. Exp. Biol. 2002, 205, 151-158. (Pubitemid 34861268)
166. 2 and ferric or cupric ions: its modulation by histidine', Free Radical Res. Commun. 1990, 9, 39-47.
167. U. Rauen, S. Klempt, H. de Groot, 'Histidine-induced injury to cultured liver cells, effects of histidine derivatives and of iron chelators', Cell. Mol. Life Sci. 2007, 64, 192-205.
168. R. A. Yokel, 'Blood-brain barrier flux of aluminum, manganese, iron and other metals suspected to contribute to metal-induced neurodegeneration', J. Alzheimers Dis. 2006, 10, 223-253.
169. L. A. G. J. M. Vanaerts, H. J. Blom, R. A. Deabreu, F. J. M. Trijbels, T. K. A. B. Eskes, J. H. J. C. Peereboom-Stegeman, J. Noordhoek, 'Prevention of neural tube defects by and toxicity of L-homocysteine in cultured postimplantation rat embryos', Teratology 1994, 50, 348-360.
170. 6 enzymes participating in selenium amino acid metabolism', BioFactors 1999, 10, 257-262.
171. H.-G. Sahl, G. Bierbaum, 'Lantibiotics: biosynthesis and biological activities of uniquely modified peptides from gram-positive bacteria', Annu. Rev. Microbiol. 1998, 52, 41-79.
172. M. Friedman, M. R. Gumbmann, 'Nutritional value and safety of methionine derivatives, isomeric dipeptides and hydroxy analogs in mice', J. Nutr. 1988, 118, 388-397.
173. J. S. Tou, B. N. Violand, Z. Y. Chen, J. A. Carroll, M. R. Schlittler, K. Egodage, S. Poruthoor, C. Lipartito, D. A. Basler, J. W. Cagney, S. B. Storrs, 'Two novel bovine somatotropin species generated from a common dehydroalanine intermediate', Protein J. 2009, 28, 87-95.
174. B. S. Borg, R. C. Wahlstrom, 'Species and isomeric variation in the utilization of amino acids', in 'Absorption and Utilization of Amino Acids', Ed. M. Friedman, CRC Press, Boca Raton, 1989, Vol. 2, pp. 155-171.
175. M. Friedman, P. A. Finot, 'Improvement in the nutritional quality of bread, Adv. Exp. Med. Biol. 1991, 289, 415-445.
176. M. Friedman, 'Food browning and its prevention: an overview', J. Agric. Food Chem. 1996, 44, 631-653.
177. B. F. Bernard, E. P. Krenning, W. A. Breeman, E. J. Rolleman, W. H. Bakker, T. J. Visser, H. Macke, M. de Jong, 'D-Lysine reduction of indium-111 octreotide and yttrium-90 octreotide renal uptake', J. Nucl. Med. 1997, 38, 1929-1933.
178. B. J. Boyd, L. M. Kaminskas, P. Karellas, G. Krippner, R. Lessene, C. J. Porter, 'Cationic poly-L-lysine dendrimers: pharmacokinetics, biodistribution, and evidence for metabolism and bioresorption after intravenous administration to rats', Mol. Pharmacol. 2006, 3, 614-627.
179. 111In-DOTATOC: a comparison among various basic amino acids', Ann. Nucl. Med. 2007, 21, 79-83.
180. M. Friedman, K. N. Pearce, 'Copper(II) and cobalt(II) affinities of LL- and LD-lysinoalanine diastereomers: implications for food safety and nutrition', J. Agric. Food Chem. 1989, 37, 123-127.
181. K. N. Pearce,M. Friedman, 'Binding of copper(II) and other metal ions by lysinoalanine and related compounds and its significance for food safety', J. Agric. Food Chem. 1988, 36, 707-717.
182. D. Danalev, M. Koleva, D. Ivanova, L. Vezenkov, N. Vassilev, 'Synthesis of two peptide mimetics as markers for chemical changes of wool s keratin during skin unhairing process', Protein Pept. Lett. 2008, 15, 353-355.
183. T. Yamauchi, M. Goto, H.-Y. Wu, T. Uo, T. Yoshimura, H. Mihara, T. Kurihara, I. Miyahara, K. Hirotsu, N. Esaki, 'Serine racemase with catalytically active lysinoalanyl residue', J. Biochem. 2009, 145, 421-424.
184. P. J. Garlick, 'Toxicity of methionine in humans', J. Nutr. 2006, 136, 1722S-1725S.
185. T. Sasamura, A. Matsuda, Y. Kokuba, 'Effects of D-methionine-containing solution on tumor cell growth in vitro', Arzneimittelforschung 1999, 49, 541-543.
186. K. C. Campbell, R. P. Meech, L. P. Rybak, L. F. Hughes, 'The effect of D-methionine on cochlear oxidative state with and without cisplatin administration: mechanisms of otoprotection', J. Am. Acad. Audiol. 2003, 14, 144-156.
187. C. Wimmer, K. Mees, P. Stumpf, U. Welsch, O. Reichel, M. Suckfüll, 'Round window application of D-methionine, sodium thiosulfate, brain-derived neurotrophic factor, and fibroblast growth factor-2 in cisplatin-induced ototoxicity', Otol. Neurotol. 2004, 25, 33-40.
188. P. W. Cheng, S. H. Liu, Y. H. Young, C. J. Hsu, S. Y. Lin-Shiau, 'Protection from noise-induced temporary threshold shift by d-methionine is associated with preservation of ATPase activities', Ear Hear. 2008, 29, 65-75.
189. S. Theneshkumar, G. Lorito, P. Giordano, J. Petruccelli, A. Martini, S. Hatzopoulos, 'Effect of noise conditioning on cisplatin-induced ototoxicity: a pilot study', Med. Sci. Monit. 2009, 15, BR173-177.
190. S. B. Vuyyuri, D. A. Hamstra, D. Khanna, C. A. Hamilton, S. M. Markwart, K. C. M. Campbell, P. Sunkara, B. D. Ross, A. Rehemtulla, 'Evaluation of D-methionine as a novel oral radiation protector for prevention of mucositis', Clin. Cancer Res. 2008, 14, 2161-2170.
191. Z. Findrik, D. Vasić-Rački, 'Biotransformation of D-methionine into L-methionine in the cascade of four enzymes', Biotechnol. Bioeng. 2007, 98, 956-967.
192. A. B. Martínez-Girón, C. García-Ruiz, A. L. Crego, M. L. Marina, 'Development of an in-capillary derivatization method by CE for the determination of chiral amino acids in dietary supplements and wines', Electrophoresis 2009, 30, 696-704.
193. F. Huang, W. Du, 'Solution structure of Hyp10Pro variant of conomarphin, a cysteine-free and D-amino-acid containing conopeptide', Toxicon 2009, 54, 153-160.
194. D. Kampel, R. Kupferschmidt, G. Lubec, 'Toxicity of D-proline', in 'Amino Acid: Chemistry, Biology and Medicine', Eds. G. Lubec, G. A. Rosenthal, Escom Science Publishers, Leiden, Netherlands, 1990, pp. 1164-1171.
195. A. Schieber, H. Brückner, M. Rupp-Classen, W. Specht, S. Nowitzki-Grimm, H.-G. Classen, 'Evaluation of D-amino acid levels in rat by gas chromatography-selected ion monitoring mass spectrometry: no evidence for subacute toxicity of orally fed D-proline and D-aspartic acid', J. Chromatogr., B: Biomed. Sci. Appl. 1997, 691, 1-12.
196. G. H. Heinz, D. J. Hoffman, L. J. LeCaptain, 'Toxicity of seleno-L-methionine, seleno-DL-methionine, high selenium wheat, and selenized yeast to mallard ducklings', Arch. Environ. Contam. Toxicol. 1996, 30, 93-99.
197. A. R. Kennedy, J. H. Ware, J. Guan, J. J. Donahue, J. E. Biaglow, Z. Zhou, J. Stewart, M. Vazquez, X. S. Wan, 'Selenomethionine protects against adverse biological effects induced by space radiation', Free Radical Biol. Med. 2004, 36, 259-266.
198. N. Esaki, H. Shimoi, H. Tanaka, K. Soda, 'Enantioselective synthesis of D-selenomethionine with D-amino acid transferase', Biotechnol. Bioeng. 1989, 34, 1231-1233.
199. M. Friedman, R. Liardon, 'Racemization kinetics of amino acid residues in alkali-treated soybean proteins', J. Agric. Food Chem. 1985, 33, 666-672.
200. R. E. Williams, E. A. Lock, 'D-Serine-induced nephrotoxicity: possible interaction with tyrosine metabolism', Toxicology 2004, 201, 231-238.
201. R. E. Williams, H. Major, E. A. Lock, E. M. Lenz, I. D. Wilson, 'D-Serine-induced nephrotoxicity: a HPLC-TOF/MS-based metabonomics approach', Toxicology 2005, 207, 179-190.
202. M. Maekawa, T. Okamura, N. Kasai, Y. Hori, K. H. Summer, R. Konno, 'D-Amino-acid oxidase is involved in d-serine-induced nephrotoxicity', Chem. Res. Toxicol. 2005, 18, 1678-1682.
203. S. Levine, A. Saltzman, 'Acute uremia produced in rats by nephrotoxic chemicals is alleviated by protein deficient diet', Renal Failure 2003, 24, 517-523.
204. A. W. Krug, K. Völker, W. H. Dantzler, S. Silbernagl, 'Why is D-serine nephrotoxic and α-aminoisobutyric acid protective?' Am. J. Physiol. Renal Physiol. 2007, 293, F382-F390.
205. R. Sethuraman, T. L. Lee, S. Tachibana, 'D-Serine regulation: a possible therapeutic approach for central nervous diseases and chronic pain', Mini Rev. Med. Chem. 2009, 9, 813-819.
206. M. M. Miller, L. B. Popova, E. A. Meleshkevitch, P. V. Tran, D. Y. Boudko, 'The invertebrate B0 system transporter, D. melanogaster NAT1, has unique D-amino acid affinity and mediates gut and brain functions', Insect Biochem. Mol. Biol. 2008, 38, 923-931.
207. A. Shimada, H. Ozaki, T. Saito, F. Noriko, 'Tryptophanase-catalyzed L-tryptophan synthesis from D-serine in the presence of diammonium hydrogen phosphate', Int. J. Mol. Sci. 2009, 10, 2578-2590.
208. G. Zanotti, N. Kobayashi, E. Munekata, S. Zobeley, H. Faulstich, 'D-Configuration of serine is crucial in maintaining the phalloidin-like conformation of viroisin', Biochemistry 1999, 38, 10723-10729.
209. M. Friedman, J. L. Cuq, 'Chemistry, analysis, nutritional value, and toxicology of tryptophan in food. A review', J. Agric. Food Chem. 1988, 36, 1079-1093.
210. B. E. Arentson, D. R. Zimmerman, 'Nutritive value of D-tryptophan for the growing pig', J. Anim. Sci. 1985, 60, 474-479.
211. K. Shibata, M. Sawabe, T. Fukuwatari, E. Sugimoto, 'Efficiency of D-tryptophan as niacin in rats', Biosci. Biotechnol. Biochem. 2000, 64, 206-209.
212. E. G. A. Carter, K. J. Carpenter, M. Friedman, 'The nutritional value of some niacin analogs for rats', Nutr. Rep. Int. 1982, 25, 389-397.
213. J. W. Finley, M. Friedman, 'New sweetening agents: N-formyl- and N′-acetylkynurenine', J. Agric. Food Chem. 1973, 21, 33-34.
214. K. Maehashi, M. Matano, A. Kondo, Y. Yamamoto, S. Udaka, 'Riboflavin-binding protein exhibits selective sweet suppression toward protein sweeteners', Chem. Senses 2007, 32, 183-190.
215. S. Manita, A. A. Bachmanov, X. Li, G. K. Beauchamp, M. Inoue, 'Is glycine 'sweet' to mice? Mouse strain differences in perception of glycine taste', Chem. Senses 2006, 31, 785-793.
216. Anonymous, 'Dietary D-tyrosine as an antimetabolite in mice', Nutr. Rev. 1985, 43, 156-158.
217. O. Soutourina, J. Soutourina, S. Blanquet, P. Plateau, 'Formation of D-tyrosyl-tRNATyr accounts for the toxicity of D-tyrosine toward Escherichia coli', J. Biol. Chem. 2004, 279, 42560-42565.
218. T. Sasamura, A. Matsuda, Y. Kokuba, 'Nutritional effects of a D-methionine-containing solution on AH109A hepatoma-bearing rats', Biosci. Biotechnol. Biochem. 1998, 62, 2418-2420.
219. M. Friedman, M. R. Gumbmann, 'Biological availability of ε-N-methyl-L-lysine, 1-N-methyl-L-histidine, and 3-N-methyl-L-histidine in mice', Nutr. Rep. Int. 1979, 19, 437-443.
220. M. Friedman, M. R. Gumbmann, 'Bioavailability of some lysine derivatives in mice', J. Nutr. 1981, 111, 1362-1369.
221. M. Friedman, M. R. Gumbmann, L. Savoie, 'The nutritional value of lysinoalanine as a source of lysine for mice', Nutr. Rep. Int. 1982, 26, 937-943.
222. S. Ohtani, 'Estimation of age from dentin by using the racemization reaction of aspartic acid', Am. J. Forensic Med. Pathol. 1995, 16, 158-161.
223. S. Ohtani, Y. Matsushima, H. Ohhira, A. Watanabe, 'Age-related changes in D-aspartic acid of rat teeth', Growth Dev. Aging 1995, 59, 55-61.
224. P. M. Masters, 'Age at death determinations for autopsied remains based on aspartic acid racemization in tooth dentin: Importance of postmortem conditions', Forensic Sci. Int. 1986, 32, 179-184.
225. S. Ohtani, Y. Matsushima, Y. Kobayashi, K. Kishi, 'Evaluation of aspartic acid racemization ratios in the human femur for age estimation', J. Forensic Sci. 1998, 43, 949-953.
226. S. Ritz, A. Turzynski, H.W. Schütz, 'Estimation of age at death based on aspartic acid racemization in noncollagenous bone proteins', Forensic Sci. Int. 1994, 69, 149-159.
227. B. J. Johnson,G. H. Miller, 'Archaeological applications of amino acid racemization', Archaeometry 1997, 39, 265-287. (Pubitemid 127363983)
228. E. H. Man, J. L. Bada, 'Dietary D-amino acids', Annu. Rev. Nutr. 1987, 7, 209-225.
229. P. M. Masters, J. L. Bada, J. S. Zigler Jr., 'Aspartic acid racemization in heavy molecular weight crystallins and water-insoluble protein from normal human lenses and cataracts', Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 1204-1208.
230. C. V. Murray-Wallace, R.W. L. Kimber, 'Further evidence for apparent 'parabolic' racemization kinetics in Quaternary molluscs', Aust. J. Earth Sci. 1993, 40, 313-317.
231. H. N. Poinar, M. Höss, J. L. Bada, S. Pääbo, 'Amino acid racemization and the preservation of ancient DNA', Science 1996, 272, 864-866. (Pubitemid 27000590)
232. L. S. Brunauer, S. Clarke, 'Age-dependent accumulation of protein residues which can be hydrolyzed to D-aspartic acid in human erythrocytes', J. Biol. Chem. 1986, 261, 12538-12543.
233. T. Geiger, S. Clarke, 'Deamidation, isomerization, and racemization at asparaginyl and aspartyl residues in peptides. Succinimide-linked reactions that contribute to protein degradation', J. Biol. Chem. 1987, 262, 785-794.
234. N. Fujii, Y. Kaji, 'Racemization of aspartyl residues of proteins in age-related disease', Seikagaku 2008, 80, 287-293.
235. Y. Kaji, 'Ocular diseases caused by accumulation of proteins with post-translational modifications', Nippon Ganka Gakkai zasshi 2009, 113, 424-442; discussion 443.
236. T. Kinouchi, S. Ishiura, Y. Mabuchi, Y. Urakami-Manaka, H. Nishio, Y. Nishiuchi, M. Tsunemi, K. Takada, M. Watanabe, M. Ikeda, H. Matsui, S. Tomioka, H. Kawahara, T. Hamamoto, K. Suzuki, Y. Kagawa, 'Mammalian D-aspartyl endopeptidase: A scavenger for noxious racemized proteins in aging', Biochem. Biophys. Res. Commun. 2004, 314, 730-736.
237. S. A. Fuchs, R. Berger, L.W. J. Klomp, T. J. de Koning, 'D-Amino acids in the central nervous system in health and disease', Mol. Genet. Metab. 2005, 85, 168-180. (Pubitemid 40840756)
238. G. A. Young, S. Kendall, A. M. Brownjohn, 'D-Amino acids in chronic renal failure and the effects of dialysis and urinary losses', Amino Acids 1994, 6, 283-293.
239. H. Brückner,M. Hausch, 'Gas chromatographic characterization of free D-amino acids in the blood serum of patients with renal disorders and of healthy volunteers', J. Chromatogr. 1993, 614, 7-17.
240. A. Soto, N. J. DelRaso, J. J. Schlager, V. T. Chan, 'D-Serine exposure resulted in gene expression changes indicative of activation of fibrogenic pathways and down-regulation of energy metabolism and oxidative stress response', Toxicology 2008, 243, 177-192.
241. D. S. Dunlop, A. Neidle, 'The origin and turnover of D-serine in brain', Biochem. Biophys. Res. Commun. 1997, 235, 26-30.
242. J.-M. Billard, 'D-Serine signalling as a prominent determinant of neuronal-glial dialogue in the healthy and diseased brain', J. Cell. Mol. Med. 2008, 12, 1872-1884.
243. L. d. B. da Silva, G. Leipnitz, B. Seminotti, C. G. Fernandes, A. P. Beskow, A. U. Amaral, M. Wajner, 'D-Serine induces lipid and protein oxidative damage and decreases glutathione levels in brain cortex of rats', Brain Res. 2009, 1256, 34-42.
244. C. Madeira, M. E. Freitas, C. Vargas-Lopes, H. Wolosker, R. Panizzutti, 'Increased brain D-amino acid oxidase (DAAO) activity in schizophrenia', Schizophr. Res. 2008, 101, 76-83.
245. G. Tsai, P. Yang, L.-C. Chung, N. Lange, J. T. Coyle, 'D-Serine added to antipsychotics for the treatment of schizophrenia', Biol. Psychiatry 1998, 44, 1081-1089. (Pubitemid 28547143)
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