Chiral instability at sulfur of S-adenosylmethionine
- 7 June 1983
- journal article
- research article
- Published by American Chemical Society (ACS) in Biochemistry
- Vol. 22 (12) , 2828-2832
- https://doi.org/10.1021/bi00281a009
Abstract
S-Adenosylmethionine, generated enzymically in chirally pure form (S configuration at sulfur), undergoes simultaneous irreversible conversion to 5''-deoxy-5''-(methylthio)adenosine and homoserine with a rate constnat of 6 .times. 10-6 s-1 at pH 7.5 and 37.degree. C and reversible conversion to an enzymically inactive stereoisomer (R configuration at sulfur) with a forward rate constant of 8 .times. 10-6 s-1 at pH 7.5 and 37.degree. C. These forms of instability require small turnover times and/or stabilization through macromolecular binding for S-adenosylmethionine, if organisms that utilize it are to avoid losses of metabolic energy.This publication has 12 references indexed in Scilit:
- Separation of rat liver methionine adenosyltransferase isozymes by hydrophobic chromatographyArchives of Biochemistry and Biophysics, 1980
- Mechanism of alkaline hydrolysis of S-adenosyl-L-methionine and related sulfonium nucleosidesJournal of the American Chemical Society, 1979
- Measurement of S-adenosyl-l-methionine levels by SP sephadex chromatographyAnalytical Biochemistry, 1978
- Determination of the absolute configuration at the sulfonium center of S-adenosylmethionine. Correlation with the absolute configuration of the diastereomeric S-carboxymethyl-(S)-methionine saltsJournal of the American Chemical Society, 1977
- New methods for preparation and analysis of S-adenosyl-(5′)-3-methylthiopropylamineAnalytical Biochemistry, 1977
- Regulation of transmethylation by an S-adenosylmethionine binding proteinBiochemical and Biophysical Research Communications, 1976
- Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 5. Role of the asymmetric sulfonium pole in the enzymic binding of S-adenosyl-L-methionineJournal of Medicinal Chemistry, 1976
- Enzymatic Cleavage of S-AdenosylmethionineJournal of Biological Chemistry, 1959
- THE STABILITY AND HYDROLYSIS OF S-ADENOSYL-METHIONINE; ISOLATION OF S-RIBOSYLMETHIONINEJournal of Biological Chemistry, 1958
- S-ADENOSYLMETHIONINE; A NEW INTERMEDIATE FORMED ENZYMATICALLY FROM l-METHIONINE AND ADENOSINETRIPHOSPHATEJournal of Biological Chemistry, 1953