Literature DB >> 11429866

Highly enantioselective and regioselective biocatalytic azidolysis of aromatic epoxides.

J H Spelberg1, J E van Hylckama Vlieg, L Tang, D B Janssen, R M Kellogg.   

Abstract

[figure: see text] The halohydrin dehalogenase from Agrobacterium radiobacter AD1 catalyzed the highly enantioselective and beta-regioselective azidolysis of (substituted) styrene oxides. By means of kinetic resolutions the remaining epoxide and the formed azido alcohol could be obtained in very high ee. In a large scale conversion, the decrease in yield and selectivity due to the uncatalyzed chemical side reaction could be overcome by slow addition of azide.

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Year:  2001        PMID： 11429866     DOI： 10.1021/ol0067540

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

Review 1.  Recent developments of the quantum chemical cluster approach for modeling enzyme reactions.

Authors:  Per E M Siegbahn; Fahmi Himo
Journal:  J Biol Inorg Chem       Date:  2009-05-13       Impact factor: 3.358

Review 2.  Expanding the enzyme universe: accessing non-natural reactions by mechanism-guided directed evolution.

Authors:  Hans Renata; Z Jane Wang; Frances H Arnold
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-03       Impact factor: 15.336

Review 3.  Enzymatic chemistry of cyclopropane, epoxide, and aziridine biosynthesis.

Authors:  Christopher J Thibodeaux; Wei-chen Chang; Hung-wen Liu
Journal:  Chem Rev       Date:  2011-10-21       Impact factor: 60.622

4.  Key residues for controlling enantioselectivity of Halohydrin dehalogenase from Arthrobacter sp. strain AD2, revealed by structure-guided directed evolution.

Authors:  Lixia Tang; Xuechen Zhu; Huayu Zheng; Rongxiang Jiang; Maja Majeric Elenkov
Journal:  Appl Environ Microbiol       Date:  2012-02-10       Impact factor: 4.792

5.  Structure and mechanism of a bacterial haloalcohol dehalogenase: a new variation of the short-chain dehydrogenase/reductase fold without an NAD(P)H binding site.

Authors:  R M de Jong; J J W Tiesinga; H J Rozeboom; K H Kalk; L Tang; D B Janssen; B W Dijkstra
Journal:  EMBO J       Date:  2003-10-01       Impact factor: 11.598

6.  Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols via regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water.

Authors:  Hai-Yang Wang; Kun Huang; Melvin De Jesús; Sandraliz Espinosa; Luis E Piñero-Santiago; Charles L Barnes; Margarita Ortiz-Marciales
Journal:  Tetrahedron Asymmetry       Date:  2016-02-15

7.  Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from Ilumatobacter coccineus: a biocatalytic approach to 2-azido-2-aryl-1-ols.

Authors:  Miao An; Wanyi Liu; Xiaoying Zhou; Ran Ma; Huihui Wang; Baodong Cui; Wenyong Han; Nanwei Wan; Yongzheng Chen
Journal:  RSC Adv       Date:  2019-05-24       Impact factor: 3.361

8.  Enhancing the biocatalytic manufacture of the key intermediate of atorvastatin by focused directed evolution of halohydrin dehalogenase.

Authors:  Yu Luo; Yangzi Chen; Hongmin Ma; ZhenHua Tian; Yeqi Zhang; Jian Zhang
Journal:  Sci Rep       Date:  2017-02-06       Impact factor: 4.379
  8 in total

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