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Chemical Compound Review

methionine     (2R)-2-amino-4- methylsulfanyl-butanoic acid

Synonyms: D-Methionin, D-Metionien, D-Methionine, R-Methionine, H-D-Met-OH, ...
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Disease relevance of D-Methionine


High impact information on D-Methionine


Chemical compound and disease context of D-Methionine


Biological context of D-Methionine


Anatomical context of D-Methionine

  • The pathways that facilitate the uptake of L-methionine (L-Met), D-methionine (D-Met) and L-2-hydroxy-4-methylthiobutanoic acid (L-HMB) were characterized in chick intestinal brush border membrane vesicles [17].
  • In previous studies we have found that porcine kidney fibroblasts will grow in medium containing D-2-hydroxy-4-methylthiobutanoic acid (D-methionine hydroxy analogue, D-MHA) as the sole source of methionine but not in medium containing the L-isomer (L-MHA) alone [18].
  • The peptide containing the D-methionine exhibited high-affinity and selectivity for delta opioid receptors in the mouse vas deferens and in rat brain homogenates [19].
  • Absorption mechanisms of L- and D-methionine (MET) in an in vitro cultured human intestinal epithelial cell model (Caco-2) and an in situ perfused rat intestinal model were investigated to determine if the kinetic characteristics of absorption are comparable in these two popular absorption models [20].
  • In this study, we attempted to examine whether cisplatin-induced vestibulotoxicity and D-methionine protection were correlated with the changes of ATPase activities and oxidative stress of ampullary tissue of vestibules as well as cerebellar cortex (the inhibitory center of VOR system) of guinea pigs [15].

Associations of D-Methionine with other chemical compounds


Gene context of D-Methionine


Analytical, diagnostic and therapeutic context of D-Methionine


  1. Construction of Modified Ribosomes for Incorporation of d-Amino Acids into Proteins. Dedkova, L.M., Fahmi, N.E., Golovine, S.Y., Hecht, S.M. Biochemistry (2006) [Pubmed]
  2. Brain tumor imaging using C-11-labeled L-methionine and D-methionine. Schober, O., Meyer, G.J., Stolke, D., Hundeshagen, H. J. Nucl. Med. (1985) [Pubmed]
  3. Non selective transport of [11C-methyl]-L-and D-methionine into a malignant glioma. Schober, O., Duden, C., Meyer, G.J., Müller, J.A., Hundeshagen, H. European journal of nuclear medicine. (1987) [Pubmed]
  4. The utilization and safety of isomeric sulfur-containing amino acids in mice. Friedman, M., Gumbmann, M.R. J. Nutr. (1984) [Pubmed]
  5. Peptidoglycan tripeptide content and cross-linking are altered in Enterobacter cloacae induced to produce AmpC beta-lactamase by glycine and D-amino acids. Ottolenghi, A.C., Caparrós, M., de Pedro, M.A. J. Bacteriol. (1993) [Pubmed]
  6. The synthetic chemoattractant Trp-Lys-Tyr-Met-Val-DMet activates neutrophils preferentially through the lipoxin A(4) receptor. Dahlgren, C., Christophe, T., Boulay, F., Madianos, P.N., Rabiet, M.J., Karlsson, A. Blood (2000) [Pubmed]
  7. Initiation of Bacillus subtilis sporulation by the stringent response to partial amino acid deprivation. Ochi, K., Kandala, J.C., Freese, E. J. Biol. Chem. (1981) [Pubmed]
  8. Utilization of D-methionine during total parenteral nutrition in postsurgical patients. Printen, K.J., Brummel, M.C., Cho, E.S., Stegink, L.D. Am. J. Clin. Nutr. (1979) [Pubmed]
  9. Increased translation efficiency and antizyme-dependent stabilization of ornithine decarboxylase in amino acid-supplemented human colon adenocarcinoma cells, Caco-2. Chabanon, H., Persson, L., Wallace, H.M., Ferrara, M., Brachet, P. Biochem. J. (2000) [Pubmed]
  10. Penicillin-insensitive incorporation of D-amino acids into cell wall peptidoglycan influences the amount of bound lipoprotein in Escherichia coli. Tsuruoka, T., Tamura, A., Miyata, A., Takei, T., Iwamatsu, K., Inouye, S., Matsuhashi, M. J. Bacteriol. (1984) [Pubmed]
  11. Antioxidants attenuate gentamicin-induced free radical formation in vitro and ototoxicity in vivo: D-methionine is a potential protectant. Sha, S.H., Schacht, J. Hear. Res. (2000) [Pubmed]
  12. Uptake kinetics of 14C L-leucine and 14C L- and 14C D-methionine in rat brain and incorporation into protein. Lauenstein, L., Meyer, G.J., Sewing, K.F., Schober, O., Hundeshagen, H. Neurosurgical review. (1987) [Pubmed]
  13. The crystal structure of beta-lactamase from Staphylococcus aureus at 0.5 nm resolution. Moult, J., Sawyer, L., Herzberg, O., Jones, C.L., Coulson, A.F., Green, D.W., Harding, M.M., Ambler, R.P. Biochem. J. (1985) [Pubmed]
  14. The metD D-methionine transporter locus of Escherichia coli is an ABC transporter gene cluster. Gál, J., Szvetnik, A., Schnell, R., Kálmán, M. J. Bacteriol. (2002) [Pubmed]
  15. D-Methionine attenuated cisplatin-induced vestibulotoxicity through altering ATPase activities and oxidative stress in guinea pigs. Cheng, P.W., Liu, S.H., Young, Y.H., Lin-Shiau, S.Y. Toxicol. Appl. Pharmacol. (2006) [Pubmed]
  16. Molecular cloning of TvDAO1, a gene encoding a D-amino acid oxidase from Trigonopsis variabilis and its expression in Saccharomyces cerevisiae and Kluyveromyces lactis. González, F.J., Montes, J., Martin, F., López, M.C., Fermiñán, E., Catalán, J., Galán, M.A., Domínguez, A. Yeast (1997) [Pubmed]
  17. Methionine and 2-hydroxy-4-methylthiobutanoic acid are transported by distinct Na(+)-dependent and H(+)-dependent systems in the brush border membrane of the chick intestinal epithelium. Maenz, D.D., Engele-Schaan, C.M. J. Nutr. (1996) [Pubmed]
  18. Basis of the stereospecific preference of porcine kidney fibroblasts for D-2-hydroxy-4-methylthiobutanoic acid as a source of methionine. Schreiner, C.L., Jones, E.E. J. Nutr. (1988) [Pubmed]
  19. Deltorphin, a novel amphibian skin peptide with high selectivity and affinity for delta opioid receptors. Kreil, G., Barra, D., Simmaco, M., Erspamer, V., Erspamer, G.F., Negri, L., Severini, C., Corsi, R., Melchiorri, P. Eur. J. Pharmacol. (1989) [Pubmed]
  20. Comparison of the transport characteristics of D- and L-methionine in a human intestinal epithelial model (Caco-2) and in a perfused rat intestinal model. Zheng, L., Chen, J., Zhu, Y., Yang, H., Elmquist, W., Hu, M. Pharm. Res. (1994) [Pubmed]
  21. Selective modification of surface-exposed thiol groups in Trigonopsis variabilisD-amino acid oxidase using poly(ethylene glycol) maleimide and its effect on activity and stability of the enzyme. Slavica, A., Dib, I., Nidetzky, B. Biotechnol. Bioeng. (2007) [Pubmed]
  22. Local administration of antioxidants to the inner ear. Kinetics and distribution(1). Laurell, G., Teixeira, M., Sterkers, O., Bagger-Sjöbäck, D., Eksborg, S., Lidman, O., Ferrary, E. Hear. Res. (2002) [Pubmed]
  23. Amino acids dilate resistance blood vessels of the perfused rat mesentery. al-Swayeh, O.A., Moore, P.K. J. Pharm. Pharmacol. (1989) [Pubmed]
  24. Different effects of sulfur amino acids on prolidase and prolinase activity in normal and prolidase-deficient human erythrocytes. Uramatsu, M., Liu, G., Uramatsu, S., Zhang, M., Wang, W., Nakayama, K., Manabe, M., Kodama, H. Clin. Chim. Acta (2007) [Pubmed]
  25. Human methionine aminopeptidase type 2 in complex with L- and D-methionine. Nonato, M.C., Widom, J., Clardy, J. Bioorg. Med. Chem. Lett. (2006) [Pubmed]
  26. Methionine and glutamine transport systems in D-methionine utilising revertants of Salmonella typhimurium. Poland, J., Ayling, P.D. Mol. Gen. Genet. (1984) [Pubmed]
  27. Simultaneous detection of both nitric oxide and reactive oxygen species in guinea pig vestibular sensory cells. Takumida, M., Anniko, M. ORL J. Otorhinolaryngol. Relat. Spec. (2002) [Pubmed]
  28. D-Amino acid dehydrogenase of Escherichia coli K12: positive selection of mutants defective in enzyme activity and localization of the structural gene. Wild, J., Klopotowski, T. Mol. Gen. Genet. (1981) [Pubmed]
  29. A novel alpha-proton exchange reaction catalyzed by Escherichia coli methionyl-tRNA synthetase. Williams, J.S., Rosevear, P.R. Biochemistry (1991) [Pubmed]
  30. Uptake of 11C-L- and D-methionine in brain tumors. Meyer, G.J., Schober, O., Hundeshagen, H. European journal of nuclear medicine. (1985) [Pubmed]
  31. Effects of equimolar doses of L-methionine, D-methionine and L-methionine-dl-sulfoxide on plasma and urinary amino acid levels in normal adult humans. Stegink, L.D., Bell, E.F., Filer, L.J., Ziegler, E.E., Andersen, D.W., Seligson, F.H. J. Nutr. (1986) [Pubmed]
  32. D-methionine utilization in young miniature pigs, adult rabbits, and adult dogs. Cho, E.S., Andersen, D.W., Filer, L.J., Stegink, L.D. JPEN. Journal of parenteral and enteral nutrition. (1980) [Pubmed]
  33. Effects of D-methionine-containing solution on tumor cell growth in vitro. Sasamura, T., Matsuda, A., Kokuba, Y. Arzneimittel-Forschung. (1999) [Pubmed]
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