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Biocatalytic Route to Chiral Precursors of β-Substituted-γ-Amino Acids

Mukherjee, Herschel and Martinez, Carlos A. (2011) Biocatalytic Route to Chiral Precursors of β-Substituted-γ-Amino Acids. ACS Catalysis, 1 (9). pp. 1010-1013. ISSN 2155-5435. https://resolver.caltech.edu/CaltechAUTHORS:20110929-141345683

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Abstract

In this work, we utilized commercial lipases (from Thermomyces lanuginosa, Rhizopus delemar, and Mucor miehei) as biocatalysts for the efficient synthesis of precursors of β-substituted-γ-amino acids. This biocatalytic route provides a practical and efficient synthesis of a wide range of optically active compounds by accepting a number of aliphatic and aromatic 3-substituted-3-cyano-2-(ethoxycarbonyl)propanoic acid ethyl esters (2) without compromising enantioselectivity or yields. The resolution step allows for the nearly quantitative recovery of the unreacted enantiomer of R-(2) as well as the newly formed 3-substituted-3-cyano-2-(ethoxycarbonyl)propanoic acid (3) in high enantio and diastereoselectivity. The use of a facile thermal decarboxylation of (3) in aqueous solution to produce 3-substituted-3-cyanopropanoic acid ethyl esters (4) enable us to prepare a wide range of optically active precursors of β-Substituted-γ-Amino Acids.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/cs2002466 DOIUNSPECIFIED
http://pubs.acs.org/doi/full/10.1021/cs2002466PublisherUNSPECIFIED
Additional Information:© 2011 American Chemical Society. Received: May 16, 2011. Revised: June 8, 2011. Published: July 19, 2011. Special Issue: Biocatalysis and Biomimetic Catalysis for Sustainability. The authors gratefully acknowledge Dr. Rajesh Kumar for helpful corrections to the manuscript. The authors gratefully acknowledge Pfizer Global Research and Development for providing support to H.M. during a summer internship.
Funders:
Funding AgencyGrant Number
Pfizer Global Research and DevelopmentUNSPECIFIED
Subject Keywords:Lipase resolution, ester hydrolysis, β-Substituted-γ-Amino Acids
Issue or Number:9
Record Number:CaltechAUTHORS:20110929-141345683
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20110929-141345683
Official Citation: Biocatalytic Route to Chiral Precursors of β-Substituted-γ-Amino Acids Herschel Mukherjee and ,Carlos A. Martinez ACS Catalysis 2011 1 (9), 1010-1013
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:25503
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:30 Sep 2011 14:45
Last Modified:03 Oct 2019 03:06

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