One-pot synthesis of (R)-1-(1-naphthyl)ethanol by stereoinversion using Candida parapsilosis

Autor:	Linga Banoth, Suyog M. Amrutkar, Uttam Chand Banerjee
Rok vydání:	2013
Předmět:	Ethanol biology Organic Chemistry One-pot synthesis Substrate (chemistry) Nonactin Alcohol Candida parapsilosis biology.organism_classification Biochemistry chemistry.chemical_compound chemistry Biocatalysis Yield (chemistry) Drug Discovery Organic chemistry Nuclear chemistry
Zdroj:	Tetrahedron Letters. 54:3274-3277
ISSN:	0040-4039
Popis:	R)-1-(1-Naphthyl)ethanol is an essential chiral substrate for the synthesis of nonactin and dihydro-(1H)- quinoline-2-one derivatives. Stereoinversion of (S)-1-(1-naphthyl)ethanol to (R)-1-(1-naphthyl)ethanol by whole cell biocatalysis, using Candida parapsilosis, is reported here. Candida parapsilosis possesses a requisite redox system for the stereoinversion of secondary alcohol. The reaction conditions (tempera- ture, time, pH, organic solvent, etc.) significantly influenced the stereoinversion process. Optimum con- ditions were found to be the reaction temperature of 30 C, a cellmass concentration of 200 mg/mL, pH 7 (phosphate buffer, 50 mM), a shaking speed of 200 rpm, and a 12 h reaction time. Under these optimum conditions, (R)-1-(1-naphthyl)ethanol was obtained in 100% eeR and 88% yield.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::85d21492f96fe6b46b2718b4ca2f49ee https://doi.org/10.1016/j.tetlet.2013.04.051 Zobrazit plný text záznamu Full Text from ScienceDirect