Enzymatic Resolution of (+/-)-Menthol Using Transesterification with Methyl (2R)-(+)-2-Chloropropanoate: A Biocatalyzed Reaction Studied by NMR Spectroscopy and Polarimetry for an Advanced Undergraduate Project in Modern Organic Chemistry

Autor:	C. Chon, C. Poiré, P. Hudhomme, C. Rabiller
Rok vydání:	1996
Předmět:	biology General Chemistry Transesterification Education Candida rugosa Kinetic resolution chemistry.chemical_compound chemistry Biocatalysis biology.protein Organic chemistry Stereoselectivity Organic synthesis Lipase Menthol
Zdroj:	Journal of Chemical Education. 73:93
ISSN:	1938-1328 0021-9584
DOI:	10.1021/ed073p93
Popis:	Lipase from Candida rugosa is used as an efficient biocatalyst for the kinetic resolution of (+/-)-Menthol. Methyl (2R)-(+)-2-chloropropanoate is chosen as an acyl donor for the transesterification reaction of menthol. Candida rugosa lipase catalyzes this transformation only with the (-)-menthol thus providing the corresponding 2-chloropropanoate with an excellent diastereomeric excess (>94%). This reaction is a part of an integrated laboratory project in stereoselective organic synthesis for advanced undergraduate students in the University of Nantes (France).
Databáze:	OpenAIRE
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