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

✍ Scribed by Waldemar Adam; Michael Lazarus; Alexandra Schmerder; Hans-Ulrich Humpf; Chantu R. Saha-Möller; Peter Schreier

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 322 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199809)1998:9<2013::aid-ejoc2013>3.0.co;2-s

✦ Synopsis

The lipase-catalyzed acetylation of a broad spectrum of configurations of the 2-hydroxy acids 1 were assigned by comparison of the gas-chromatographic data with that of racemic 2-hydroxy acids 1 to their 2-acetoxy acids 2 was shown to proceed with high enantioselectivity. Thus, the literature-known reference compounds, or by means of the exciton-coupled circular dichroism method (ECCD) on their microbial lipases, in particular from Candida antarctica and Burkholderia species, are convenient biocatalysts for the bichromophoric 2-naphthoate 9-anthrylmethyl derivatives 3.

These results establish that (S)-2-hydroxy acids 1 were synthesis of optically active 2-hydroxy acids in excellent enantioselectivity (ee values up to Ͼ 99%). The absolute preferentially acetylated by microbial lipases.