Literature DB >> 30353294

Dynamic kinetic resolution of Vince lactam catalyzed by γ-lactamases: a mini-review.

Shaozhou Zhu1, Guojun Zheng2.   

Abstract

γ-Lactamases are versatile enzymes used for enzymatic kinetic resolution of racemic Vince lactam (2-azabicyclo[2.2.1]hept-5-en-3-one) in the industry. Optically pure enantiomers and their hydrolytic products are widely employed as key chemical intermediates for developing a wide range of carbocyclic nucleoside medicines, including US FDA-approved drugs peramivir and abacavir. Owing to the broad applications in the healthcare industry, the resolution process of Vince lactam has witnessed tremendous progress during the past decades. Some of the most important advances are the enzymatic strategies involving γ-lactamases. The strong industrial demand drives the progress in various strategies for discovering novel biocatalysts. In the past few years, several new scientific breakthroughs, including the genome-mining strategy and elucidation of several crystal structures, boosted the research on γ-lactamases. So far, several families of γ-lactamases for resolution of Vince lactam have been discovered, and their number is continuously increasing. The purpose of this mini-review is to describe the discovery strategy and classification of these intriguing enzymes and to cover our current knowledge on their potential biological functions. Moreover, structural properties are described in addition to their possible catalytic mechanisms. Additionally, recent advances in the newest approaches, such as immobilization to increase stability, and other engineering efforts are introduced.

Entities:  

Keywords:  Abacavir; Acetamidase; Biocatalysis; Carbocyclic nucleosides; Enzymatic kinetic resolution; Formamidase; Gamma lactamase; Isochorismatase; Signature amidase; Vince lactam

Mesh:

Substances:

Year:  2018        PMID: 30353294     DOI: 10.1007/s10295-018-2093-6

Source DB:  PubMed          Journal:  J Ind Microbiol Biotechnol        ISSN: 1367-5435            Impact factor:   3.346


  61 in total

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Authors:  A Scotto d'Abusco; S Ammendola; R Scandurra; L Politi
Journal:  Extremophiles       Date:  2001-06       Impact factor: 2.395

2.  Regioselective hydroarylations and parallel kinetic resolution of Vince lactam.

Authors:  Adam S Kamlet; Cathy Préville; Kathleen A Farley; David W Piotrowski
Journal:  Angew Chem Int Ed Engl       Date:  2013-08-16       Impact factor: 15.336

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Authors:  Timo Davids; Marlen Schmidt; Dominique Böttcher; Uwe T Bornscheuer
Journal:  Curr Opin Chem Biol       Date:  2013-03-21       Impact factor: 8.822

Review 4.  Carbocyclic nucleosides (carbanucleosides) as new therapeutic leads.

Authors:  Stewart W Schneller
Journal:  Curr Top Med Chem       Date:  2002-10       Impact factor: 3.295

5.  Purification, cloning, and primary structure of a new enantiomer-selective amidase from a Rhodococcus strain: structural evidence for a conserved genetic coupling with nitrile hydratase.

Authors:  J F Mayaux; E Cerbelaud; F Soubrier; P Yeh; F Blanche; D Pétré
Journal:  J Bacteriol       Date:  1991-11       Impact factor: 3.490

6.  Studies on neplanocin A, new antitumor antibiotic. I. Producing organism, isolation and characterization.

Authors:  S Yaginuma; N Muto; M Tsujino; Y Sudate; M Hayashi; M Otani
Journal:  J Antibiot (Tokyo)       Date:  1981-04       Impact factor: 2.649

7.  Enzymatic preparation of optically pure (+)-2-azabicyclo[2.2.1]hept-5-en-3-one by (-)-γ-lactamase from Bradyrhizobium japonicum USDA 6.

Authors:  Shaozhou Zhu; Lu Ren; Songzhu Yu; Cuiyu Gong; Dawei Song; Guojun Zheng
Journal:  Bioorg Med Chem Lett       Date:  2014-09-02       Impact factor: 2.823

8.  Engineering the Enantioselectivity and Thermostability of a (+)-γ-Lactamase from Microbacterium hydrocarbonoxydans for Kinetic Resolution of Vince Lactam (2-Azabicyclo[2.2.1]hept-5-en-3-one).

Authors:  Shuaihua Gao; Shaozhou Zhu; Rong Huang; Hongxia Li; Hao Wang; Guojun Zheng
Journal:  Appl Environ Microbiol       Date:  2017-12-15       Impact factor: 4.792

9.  Structural insights into the γ-lactamase activity and substrate enantioselectivity of an isochorismatase-like hydrolase from Microbacterium hydrocarbonoxydans.

Authors:  Shuaihua Gao; Yu Zhou; Weiwei Zhang; Wenhe Wang; You Yu; Yajuan Mu; Hao Wang; Xinqi Gong; Guojun Zheng; Yue Feng
Journal:  Sci Rep       Date:  2017-03-15       Impact factor: 4.379

Review 10.  Enzymes from Extreme Environments and Their Industrial Applications.

Authors:  Jennifer A Littlechild
Journal:  Front Bioeng Biotechnol       Date:  2015-10-13
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2.  "Fishing and Hunting"-Selective Immobilization of a Recombinant Phenylalanine Ammonia-Lyase from Fermentation Media.

Authors:  Evelin Sánta-Bell; Zsófia Molnár; Andrea Varga; Flóra Nagy; Gábor Hornyánszky; Csaba Paizs; Diána Balogh-Weiser; László Poppe
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Review 3.  Nanoreactor Design Based on Self-Assembling Protein Nanocages.

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  3 in total

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