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Methionine and derivatives: Exploring chirality at sulfur
Article first published online: 3 NOV 2006
DOI: 10.1002/bmb.2005.49403304274
Copyright © 2005 International Union of Biochemistry and Molecular Biology, Inc.
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How to Cite
Bentley, R. (2005), Methionine and derivatives: Exploring chirality at sulfur. Biochem. Mol. Biol. Educ., 33: 274–276. doi: 10.1002/bmb.2005.49403304274
Publication History
- Issue published online: 3 NOV 2006
- Article first published online: 3 NOV 2006
- Manuscript Revised: 27 JAN 2005
- Manuscript Received: 18 NOV 2004
REFERENCES
- 1, (2004) Environmental VOSCs–Formation and degradation of dimethyl sulfide, methanethiol and related materials, Chemosphere 55, 291–317.
- 2, (1982) Chiral organosulfur compounds, in Topics in Stereochemistry (N. L.Allinger, E. L.Eliel, S. H.Wilen, eds.) Vol. 13, pp. 333–468, Interscience, New York.
- 3, , (2003) Many paths to methyl transfer: A chronicle of convergence, Trends Biochem. Sci. 28, 329–335.
- 4, , , (1959) S-Adenosylmethionine: The relation of configuration at the sulfonium center to enzymatic activity, J. Am. Chem. Soc. 81, 3975–3980.
- 5, , , , (1977) Determination of the absolute configuration at the sulfonium center of S-adenosylmethionine. Correlation with the absolute configuration of the diastereomeric S-carboxymethyl-(S)-methionine salt, J. Am. Chem. Soc. 99, 7292–7300.
- 6(1986) Chromatographic analysis of the chiral and covalent instability of S-adenosylmethionine, Biochemistry 25, 4444–4449.
- 7, , , , , (2003) Synthetic decarboxylated S-adenosyl-l-methionine as a substrate for aminopropyltransferases, Biol. Pharm. Bull. 26, 1005–1008.
- 8, , (1984) Stereochemical course of the biosynthesis of 1-aminocyclopropane-1-carboxylate. I. Role of the asymmetric sulfonium pole and the α-amino acid center, Biochem. Biophys. Res. Comm. 121, 181–187.
- 9, (1989) Specificity of S-adenosyl-l-methionine in the inactivation and the labeling of 1-aminocyclopropane-1-carboxylate synthase isolated from tomato fruits, Arch. Biochem. Biophys. 271, 107–112.
- 10IUPAC-IUB Joint Commission on Biochemical Nomenclature (1984) Nomenclature and symbolism for amino acids and peptides. Recommendations 1983, Eur. J. Biochem. 138, 9–37.Direct Link:
- 11, (1966) The isolation of l-(+)-methionine sulfoxide from the blowfly, Phormia regina Meiger, Biochem. J. 100, 473–478.
- 12, (1965) The absolute configuration of methionine sulphoxide, Chem. Comm. 225–226.
- 13, , (2000) Oxidation of methionine in proteins: Roles in antioxidant defense and cellular regulation, IUBMB Life 50, 301–307.
- 14, , , (1999) Diastereoselective reduction of protein-bound methionine sulfoxide by methionine sulfoxide reductase, FEBS Lett. 247–250.
- 15, , , , , (2000) Identification and characterization of a putative active site for peptide methionine sulfoxide reductase (MsrA) and its substrate stereospecificity, J. Biol. Chem. 275, 14167–14172.
- 16, , , , , , , , , , (2002) High-quality life extension by the enzyme peptide methionine sulfoxide reductase, Proc. Natl. Acad. Sci. U.S.A. 99, 2748–2753.
- 17, (2004) Methionine sulfoxide reduction in mammals: Characterization of methionine-R-sulfoxide reductases, Mol. Cell. Biol. 15, 1055–1064.
- 18, , , , (2002) Selenoprotein R is a zinc-containing stereo-specific methionine sulfoxide reductase, Proc. Natl. Acad. Sci. U.S.A. 99, 4245–4250.
- 19, , , , , , (1993) Absolute configuration of l-methionine sulfoximine as a toxic principle in Cnestis palala (LOUR.) MERR, Chem. Pharm. Bull. 41, 388–390.
- 20, (1970) Crystal and molecular structure of (2S, SR)-methionine sulphoximine, J. Chem. Soc. B 694–699.
- 21, , , (2000) Structure-function relationships of glutamine synthetases, Biochim. Biophys. Acta 1477, 122–145.
- 22, , , (1982) On the binding of l-S- and l-R-diastereoisomers of the substrate analog l-methionine sulfoximine to glutamate synthetase from Escherichia coli, J. Biol. Chem. 257, 8238–8243.
- 23, , (1991) Analytical and preparative separation of the diastereoisomers of l-buthionine (SR)-sulfoximine, a potent inhibitor of glutathione biosynthesis, Anal. Biochem. 194, 268–277.
- 24, , (2003) A proton-pump inhibitor expedition: The case histories of omeprazole and esomeprazole, Nature Rev./Drug Disc. 2, 132–139.

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