Synthesis of Optically Active α-Hydroxy Acids by Kinetic Resolution Through Lipase-Catalyzed Enantioselective Acetylation

Autor:	Waldemar Adam, Michael Lazarus, Hans-Ulrich Humpf, Alexandra Schmerder, Chantu R. Saha-Möller, Peter Schreier
Rok vydání:	1998
Předmět:	Enantioselective acetylation Circular dichroism biology Stereochemistry Chemistry Organic Chemistry Optically active Catalysis Kinetic resolution Biocatalysis Acetylation biology.protein Organic chemistry Physical and Theoretical Chemistry Lipase
Zdroj:	Scopus-Elsevier
ISSN:	1099-0690 1434-193X
DOI:	10.1002/(sici)1099-0690(199809)1998:9<2013::aid-ejoc2013>3.0.co;2-s
Popis:	The lipase-catalyzed acetylation of a broad spectrum of racemic 2-hydroxy acids 1 to their 2-acetoxy acids 2 was shown to proceed with high enantioselectivity. Thus, the microbial lipases, in particular from Candidaantarctica and Burkholderiaspecies, are convenient biocatalysts for the synthesis of optically active 2-hydroxy acids in excellent enantioselectivity (ee values up to > 99%). The absolute configurations of the 2-hydroxy acids 1 were assigned by comparison of the gas-chromatographic data with that of literature-known reference compounds, or by means of the exciton-coupled circular dichroism method (ECCD) on their bichromophoric 2-naphthoate 9-anthrylmethyl derivatives 3. These results establish that (S)-2-hydroxy acids 1 were preferentially acetylated by microbial lipases.
Databáze:	OpenAIRE
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