Preparation of both enantiomers of methyl 3-benzoyloxypentanoate by enzyme-catalysed hydrolysis of corresponding racemic nitrile and amide

Autor:	Hiromichi Ohta, Masahiro Yokoyama, Takeshi Sugai, Nori Imai
Rok vydání:	1996
Předmět:	Nitrile Chemistry Stereochemistry Process Chemistry and Technology Enantioselective synthesis Bioengineering Biochemistry Catalysis Amidase Kinetic resolution chemistry.chemical_compound Nitrile hydratase Amide Organic chemistry Enantiomer Enantiomeric excess
Zdroj:	Journal of Molecular Catalysis B: Enzymatic. 1:135-141
ISSN:	1381-1177
DOI:	10.1016/1381-1177(95)00021-6
Popis:	Rhodococcus rhodochrous IFO 15564 enantioselectively hydrolysed racemic 3-benzoyloxypentanenitrile and 3-benzoyloxypentanamide to afford ( R )-amide and ( S )-car☐ylic acid with high enantiomeric excess (> 90%). In this reaction, both enantiomers of the starting nitrile were converted to the amide by nitrile hydratase, and amidase-catalysed enantioselective hydrolysis of the amide was responsible for the kinetic resolution. The lack of enantioselectivity of the nittile hydratase toward the racemic nitrile forms a marked contrast to the case of previously reported highly enantioselective conversion of prochiral 3-benzoyloxypentanedinitrile by this enzyme. since ( R )-amide could be hydrolysed chemically to ( R )-car☐ylic acid without any loss of its ee, the present microbial kinetic resolution serves as an effective method for preparing both enantiomers of synthetically useful 3-hydroxypentanoic acid derivatives.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::1ee47e658ed5d902172e13fce5508d4e https://doi.org/10.1016/1381-1177(95)00021-6 Zobrazit plný text záznamu Full Text from ScienceDirect