Literature DB >> 9343358

Synthesis of enantiopure epoxides through biocatalytic approaches.

A Archelas1, R Furstoss.   

Abstract

Enantiopure epoxides, as well as their corresponding vicinal diols, are valuable intermediates in fine organic synthesis, in particular for the preparation of biologically active compounds. The necessity of preparing such target molecules in an optically pure form has triggered much research, leading to the emergence of various new methods based on either conventional chemistry or enzymatically catalyzed reactions. In this review, we focus on the biocatalytic approaches, which include direct epoxidation of olefinic double bonds as well as indirect biocatalytic methods, and which allow for the synthesis of these important chiral building blocks in enantiomerically enriched or even enantiopure form.

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Year:  1997        PMID: 9343358     DOI: 10.1146/annurev.micro.51.1.491

Source DB:  PubMed          Journal:  Annu Rev Microbiol        ISSN: 0066-4227            Impact factor:   15.500


  9 in total

1.  Structure and reactivity of hydroxypropylphosphonic acid epoxidase in fosfomycin biosynthesis by a cation- and flavin-dependent mechanism.

Authors:  Karen McLuskey; Scott Cameron; Friedrich Hammerschmidt; William N Hunter
Journal:  Proc Natl Acad Sci U S A       Date:  2005-09-26       Impact factor: 11.205

2.  Enzymatic resolution of racemic phenyloxirane by a novel epoxide hydrolase from Aspergillus niger SQ-6 and its fed-batch fermentation.

Authors:  Yanbin Liu; Qian Sha; Sheng Wu; Jianjun Wang; Liu Yang; Wanru Sun
Journal:  J Ind Microbiol Biotechnol       Date:  2005-12-01       Impact factor: 3.346

3.  Cloning and molecular characterization of a soluble epoxide hydrolase from Aspergillus niger that is related to mammalian microsomal epoxide hydrolase.

Authors:  M Arand; H Hemmer; H Dürk; J Baratti; A Archelas; R Furstoss; F Oesch
Journal:  Biochem J       Date:  1999-11-15       Impact factor: 3.857

4.  Toluene monooxygenase-catalyzed epoxidation of alkenes.

Authors:  K McClay; B G Fox; R J Steffan
Journal:  Appl Environ Microbiol       Date:  2000-05       Impact factor: 4.792

5.  Expression, characterization, and improvement of a newly cloned halohydrin dehalogenase from Agrobacterium tumefaciens and its application in production of epichlorohydrin.

Authors:  Zhi-Qiang Liu; Ai-Cun Gao; Ya-Jun Wang; Yu-Guo Zheng; Yin-Chu Shen
Journal:  J Ind Microbiol Biotechnol       Date:  2014-04-29       Impact factor: 3.346

6.  Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis.

Authors:  Aaron L Featherston; Scott J Miller
Journal:  Bioorg Med Chem       Date:  2016-07-11       Impact factor: 3.641

7.  Screening enantioselective epoxide hydrolase activities from marine microorganisms: detection of activities in Erythrobacter spp.

Authors:  Young-Ok Hwang; Sung Gyun Kang; Jung-Hee Woo; Kye Kyung Kwon; Takako Sato; Eun Yeol Lee; Myong Soo Han; Sang-Jin Kim
Journal:  Mar Biotechnol (NY)       Date:  2008-01-24       Impact factor: 3.619

8.  Catalytic triad of microsomal epoxide hydrolase: replacement of Glu404 with Asp leads to a strongly increased turnover rate.

Authors:  M Arand; F Müller; A Mecky; W Hinz; P Urban; D Pompon; R Kellner; F Oesch
Journal:  Biochem J       Date:  1999-01-01       Impact factor: 3.857

Review 9.  Bio-click chemistry: a bridge between biocatalysis and click chemistry.

Authors:  Diego F Rodríguez; Yanina Moglie; César A Ramírez-Sarmiento; Sachin Kumar Singh; Kamal Dua; Flavia C Zacconi
Journal:  RSC Adv       Date:  2022-01-12       Impact factor: 3.361

  9 in total

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