HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS		QUICK SEARCH:   [advanced] Author: Keyword(s): Year:  Vol:  Page:

This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Citing Articles Citing Articles via Google Scholar Google Scholar Articles by Amster, J. Articles by Tanaka, K. Search for Related Content PubMed PubMed Citation Articles by Amster, J. Articles by Tanaka, K. Social Bookmarking                      What's this?

J. Biol. Chem., Vol. 255, Issue 1, 119-120, 01, 1980

Metabolism in rats in vivo of (2S)[3,3,3-2H3]isobutyrate. Identification of (2-pro-S)methyl group as the source of a proton in dehydrogenation

J Amster and K Tanaka

(2S)[3,3,3-2H3]Isobutyrate, sodium salt, was synthesized and administered intraperitoneally to normal rats. Urinary organic acids were analyzed by gas chromatography-mass spectrometry. 3- Hydroxyisobutyric acid excreted by the rats, analyzed as both a methyl and an isopropyl ester, was found to be enriched almost exclusively with two deuteriums in the hydroxymethyl moiety of the molecule. This result, together with our previous observation that deuterium of [2- 2H1]isobutyrate was lost before the formation of 3-hydroxyisobutyrate, indicates that isobutyric acid is dehydrogenated stereospecifically at the (2-pro-S)methyl and alpha-methine groups. The resulting methacrylate is then hydrated with hydrogen addition to the same side of the molecule as it was abstracted from to produce (S)(+)-3- hydroxyisobutyric acid.
CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    What's this?