Biocatalytic Route to Chiral Precursors of β-Substituted-γ-Amino Acids
- Creators
- Mukherjee, Herschel
- Martinez, Carlos A.
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.
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.Attached Files
Supplemental Material - cs2002466_si_001.pdf
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Additional details
- Eprint ID
- 25503
- Resolver ID
- CaltechAUTHORS:20110929-141345683
- Pfizer Global Research and Development
- Created
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2011-09-30Created from EPrint's datestamp field
- Updated
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2021-11-09Created from EPrint's last_modified field