ISSN:
1434-193X
Keywords:
Lipase
;
2-Hydroxy acids
;
Kinetic resolution
;
Acetylation
;
Biocatalysis
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
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