Literature DB >> 18421383

Enzymatic resolution and evaluation of enantiomers of cis-5'-hydroxythalidomide.

Takeshi Yamamoto1, Norio Shibata, Masayuki Takashima, Shuichi Nakamura, Takeshi Toru, Nozomu Matsunaga, Hideaki Hara.   

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.

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Year:  2008        PMID： 18421383     DOI： 10.1039/b802459f

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  6 in total

Review 1.  Current status of thalidomide and CC-5013 in the treatment of metastatic prostate cancer.

Authors:  Tristan M Sissung; Silja Thordardottir; Erin R Gardner; William D Figg
Journal:  Anticancer Agents Med Chem       Date:  2009-12       Impact factor: 2.505

2.  3-(2,6-Dioxopiperidin-3-yl)-3-aza-bicyclo-[3.2.0]heptane-2,4-dione.

Authors:  Yousef M Hijji; Ellis Benjamin; Earl Benjamin; Ray J Butcher; Jerry P Jasinski
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-01-28

3.  Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications.

Authors:  Mayaka Maeno; Etsuko Tokunaga; Takeshi Yamamoto; Toshiya Suzuki; Yoshiyuki Ogino; Emi Ito; Motoo Shiro; Toru Asahi; Norio Shibata
Journal:  Chem Sci       Date:  2014-10-30       Impact factor: 9.825

4.  Antiangiogenic Activity and in Silico Cereblon Binding Analysis of Novel Thalidomide Analogs.

Authors:  Megan L Peach; Shaunna L Beedie; Cindy H Chau; Matthew K Collins; Suzana Markolovic; Weiming Luo; David Tweedie; Christian Steinebach; Nigel H Greig; Michael Gütschow; Neil Vargesson; Marc C Nicklaus; William D Figg
Journal:  Molecules       Date:  2020-12-02       Impact factor: 4.411

5.  Enzymatic Synthesis and Molecular Modelling Studies of Rhamnose Esters Using Lipase from Pseudomonas stutzeri.

Authors:  Cecilia García-Oliva; Almudena Perona; Ángel Rumbero; Pilar Hoyos; María J Hernáiz
Journal:  Int J Mol Sci       Date:  2022-02-17       Impact factor: 5.923

6.  Understanding the Thalidomide Chirality in Biological Processes by the Self-disproportionation of Enantiomers.

Authors:  Etsuko Tokunaga; Takeshi Yamamoto; Emi Ito; Norio Shibata
Journal:  Sci Rep       Date:  2018-11-20       Impact factor: 4.379
  6 in total

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