Chemical Racemization of Methyl L-β-Acetylthioisobutyrate

Methyl L-β-acetylthioisobutyrate was racemized with 1,8-diazabicyclo-[5.4.0]-undecene-7 as a catalyst. Methyl methacrylate and thioacetic acid were identified as the intermediates of the reaction. Thioacetic acid was relatively unstable and susceptible to decomposition during the racemization proces...

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Bibliographic Details
Published inBioscience, biotechnology, and biochemistry Vol. 57; no. 1; pp. 17 - 19
Main Authors Sakimae, Akihiro, Kobayashi, Yoshimasa, Ohsuga, Naoto, Numazawa, Ryozo, Ohnishi, Hisao
Format Journal Article
LanguageEnglish
Published Tokyo Taylor & Francis 01.01.1993
Japan Society for Bioscience Biotechnology and Agrochemistry
Subjects
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Racemization
Catalytic reaction
Aliphatic compound
Thioester
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Summary:Methyl L-β-acetylthioisobutyrate was racemized with 1,8-diazabicyclo-[5.4.0]-undecene-7 as a catalyst. Methyl methacrylate and thioacetic acid were identified as the intermediates of the reaction. Thioacetic acid was relatively unstable and susceptible to decomposition during the racemization process. The addition of excess methyl mechacrylate to the reaction mixture prevented a decrease of the racemate. The racemized ester was confirmed to be usable as a substrate for the enzymatic production of D-β-acetylthioisobutyric acid.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0916-8451
1347-6947
DOI:10.1271/bbb.57.17