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Issue 9, 2008
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Enzymatic resolution and evaluation of enantiomers of cis-5′-hydroxythalidomide

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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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Publication details

The article was received on 13 Feb 2008, accepted on 18 Mar 2008 and first published on 28 Mar 2008


Article type: Communication
DOI: 10.1039/B802459F
Citation: 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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