Issue 9, 2008
From the journal:

Organic & Biomolecular Chemistry

Enzymatic resolution and evaluation of enantiomers of cis-5′-hydroxythalidomide†

Takeshi Yamamoto,a   Norio Shibata,*a   Masayuki Takashima,a   Shuichi Nakamura,a   Takeshi Toru,a   Nozomu Matsunagab  and  Hideaki Harab  

* Corresponding authors

a Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan
E-mail: nozshiba@nitech.ac.jp
Fax: +81-52-735-5442
Tel: +81-52-735-5442

b Department of Biofunctional Evaluation, Molecular Pharmacology, Gifu Pharmaceutical University, Mitahora-higashi, Gifu 502-8585, Japan

Abstract

The straightforward synthesis of both enantiomers of cis-5′-hydroxythalidomide, a major metabolite of thalidomide, has been accomplished by enzymatic kinetic resolution of a racemic substrate catalyzed by Pseudomonas stutzeri lipase TL. cis-5′-Hydroxythalidomide shows resistance to racemization (and epimerization) at physiological pH. A tube formation assay to assess the ability to inhibit angiogenesis revealed that cis-5′-hydroxythalidomides are inactive.

Graphical abstract: Enzymatic resolution and evaluation of enantiomers of cis-5′-hydroxythalidomide

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Article information

DOI
https://doi.org/10.1039/B802459F
Article type
Communication
Submitted
13 Feb 2008
Accepted
18 Mar 2008
First published
28 Mar 2008

Org. Biomol. Chem., 2008,6, 1540-1543

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Enzymatic resolution and evaluation of enantiomers of cis-5′-hydroxythalidomide

T. Yamamoto, N. Shibata, M. Takashima, S. Nakamura, T. Toru, N. Matsunaga and H. Hara, Org. Biomol. Chem., 2008, 6, 1540 DOI: 10.1039/B802459F

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