☆ 4.5 Article

Synthesis of (R)-β-nitro alcohols catalyzed by R-selective hydroxynitrile lyase from Arabidopsis thaliana in the aqueous-organic biphasic system

JOURNAL OF BIOTECHNOLOGY (2011)

期刊

JOURNAL OF BIOTECHNOLOGY

卷 153, 期 3-4, 页码 153-159

出版社

ELSEVIER SCIENCE BV

DOI: 10.1016/j.jbiotec.2011.03.011

关键词

Hydroxynitrile lyase; Enzyme-catalyzed reaction; Carbon-carbon bond formation; Asymmetric Henry reaction; Optically active beta-nitro alcohol; Arabidopsis thaliana

类别

Biotechnology & Applied Microbiology

资金

Japan Society for the Promotion of Science (JSPS) [20380053]
Grants-in-Aid for Scientific Research [23248015, 20380053] Funding Source: KAKEN

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摘要

Both enantiomers of beta-nitro alcohols are versatile chiral building blocks. However, their synthesis using enzymes as catalysts has received little attention, with the exception of (S)-beta-nitro alcohols produced in a reaction catalyzed by an S-selective hydroxynitrile lyase (HNL) from Hevea brasiliensis (HbHNL). An R-selective HNL containing an alpha/beta-hydrolase fold from the noncyanogenic plant Arabidopsis thaliana (AtHNL) accepts nitromethane (MeNO2) as a donor in a reaction with aromatic aldehydes to yield (R)-beta-nitro alcohols (Henry reaction; nitro aldol reaction). This reaction proceeded in an aqueous-organic biphasic system. The organic solvent giving the highest enantioselectivity was n-butyl acetate (AcOBu) with an optimum aqueous phase content of 50% (v/v). This is the first example of the R-HNL-catalyzed synthesis of (R)-beta-nitro alcohols. (C) 2011 Elsevier B.V. All rights reserved.

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