Literature DB >> 15355089

Epoxide hydrolase-catalyzed enantioselective synthesis of chiral 1,2-diols via desymmetrization of meso-epoxides. lzhao@diversa.com.

Lishan Zhao1, Bin Han, Zilin Huang, Mark Miller, Hongjun Huang, Dan S Malashock, Zuolin Zhu, Aileen Milan, Dan E Robertson, David P Weiner, Mark J Burk.   

Abstract

The discovery, from nature, of a diverse set of microbial epoxide hydrolases is reported. The utility of a library of epoxide hydrolases in the synthesis of chiral 1,2-diols via desymmetrization of a wide range of meso-epoxides, including cyclic as well as acyclic alkyl- and aryl-substituted substrates, is demonstrated. The chiral (R,R)-diols were furnished with high ee's and yields. The discovery of the first microbial epoxide hydrolases providing access to complementary (S,S)-diols is also described.

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Year:  2004        PMID: 15355089     DOI: 10.1021/ja0466210

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  9 in total

1.  Pseudomonas aeruginosa Cif defines a distinct class of α/β epoxide hydrolases utilizing a His/Tyr ring-opening pair.

Authors:  Christopher D Bahl; Dean R Madden
Journal:  Protein Pept Lett       Date:  2012-02       Impact factor: 1.890

2.  Effect of ionic liquids on epoxide hydrolase-catalyzed synthesis of chiral 1,2-diols.

Authors:  Cinzia Chiappe; Elsa Leandri; Bruce D Hammock; Christophe Morisseau
Journal:  Green Chem       Date:  2007       Impact factor: 10.182

3.  A broadly applicable and practical oligomeric (salen) Co catalyst for enantioselective epoxide ring-opening reactions.

Authors:  David E White; Pamela M Tadross; Zhe Lu; Eric N Jacobsen
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

4.  Diversity and biocatalytic potential of epoxide hydrolases identified by genome analysis.

Authors:  Bert van Loo; Jaap Kingma; Michael Arand; Marcel G Wubbolts; Dick B Janssen
Journal:  Appl Environ Microbiol       Date:  2006-04       Impact factor: 4.792

5.  Tungsten-catalyzed regio- and enantioselective aminolysis of trans-2,3-epoxy alcohols: an entry to virtually enantiopure amino alcohols.

Authors:  Chuan Wang; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-19       Impact factor: 15.336

6.  Active-Site Flexibility and Substrate Specificity in a Bacterial Virulence Factor: Crystallographic Snapshots of an Epoxide Hydrolase.

Authors:  Kelli L Hvorecny; Christopher D Bahl; Seiya Kitamura; Kin Sing Stephen Lee; Bruce D Hammock; Christophe Morisseau; Dean R Madden
Journal:  Structure       Date:  2017-04-06       Impact factor: 5.006

7.  New Thermophilic α/β Class Epoxide Hydrolases Found in Metagenomes From Hot Environments.

Authors:  Erica Elisa Ferrandi; Christopher Sayer; Simone Antonio De Rose; Elisa Guazzelli; Carlotta Marchesi; Vahid Saneei; Michail N Isupov; Jennifer A Littlechild; Daniela Monti
Journal:  Front Bioeng Biotechnol       Date:  2018-10-16

8.  Lipase Catalysed Kinetic Resolution of Racemic 1,2-Diols Containing a Chiral Quaternary Center.

Authors:  Gonzalo de Gonzalo
Journal:  Molecules       Date:  2018-06-29       Impact factor: 4.411

9.  Identification and catalytic properties of new epoxide hydrolases from the genomic data of soil bacteria.

Authors:  Gorjan Stojanovski; Dragana Dobrijevic; Helen C Hailes; John M Ward
Journal:  Enzyme Microb Technol       Date:  2020-05-12       Impact factor: 3.493

  9 in total

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