Literature DB >> 24166888

Stereospecific biosynthesis of β-methyltryptophan from (L)-tryptophan features a stereochemical switch.

Yi Zou1, Qi Fang, Haixing Yin, Zutao Liang, Dekun Kong, Linquan Bai, Zixin Deng, Shuangjun Lin.   

Abstract

Make the switch: The three-enzyme cassette MarG/H/I is responsible for stereospecific biosynthesis of β-methyltryptophan from L-tryptophan (1). MarG/I convert 1 into (2S,3R)-β-methyltryptophan, while MarG/I combined with MarH convert 1 into (2S,3S)-β-methyltryptophan. MarH serves as a stereochemical switch by catalyzing the stereoinversion of the β-stereocenter.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  biosynthesis; cupin proteins; epimerases; reaction mechanism; β-methylamino acids

Mesh：

Substances：

Year:  2013        PMID： 24166888     DOI： 10.1002/anie.201306255

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  7 in total

1.  Synthesis of β-Branched Tryptophan Analogues Using an Engineered Subunit of Tryptophan Synthase.

Authors:  Michael Herger; Paul van Roye; David K Romney; Sabine Brinkmann-Chen; Andrew R Buller; Frances H Arnold
Journal:  J Am Chem Soc       Date:  2016-07-01       Impact factor: 15.419

2.  Xantholipin B produced by the stnR inactivation mutant Streptomyces flocculus CGMCC 4.1223 WJN-1.

Authors:  Sifan Wu; Tingting Huang; Dan Xie; Jing Wo; Xiaozheng Wang; Zixin Deng; Shuangjun Lin
Journal:  J Antibiot (Tokyo)       Date:  2016-06-22       Impact factor: 2.649

3.  In vitro reconstitution of indolmycin biosynthesis reveals the molecular basis of oxazolinone assembly.

Authors:  Yi-Ling Du; Lona M Alkhalaf; Katherine S Ryan
Journal:  Proc Natl Acad Sci U S A       Date:  2015-02-17       Impact factor: 11.205

4.  Tryptophan Synthase Uses an Atypical Mechanism To Achieve Substrate Specificity.

Authors:  Andrew R Buller; Paul van Roye; Javier Murciano-Calles; Frances H Arnold
Journal:  Biochemistry       Date:  2016-12-13       Impact factor: 3.162

Review 5.  Tryptophan Synthase: Biocatalyst Extraordinaire.

Authors:  Ella Watkins-Dulaney; Sabine Straathof; Frances Arnold
Journal:  Chembiochem       Date:  2020-09-22       Impact factor: 3.164

6.  Identification of (2S,3S)-β-Methyltryptophan as the Real Biosynthetic Intermediate of Antitumor Agent Streptonigrin.

Authors:  Dekun Kong; Yi Zou; Zhang Zhang; Fei Xu; Nelson L Brock; Liping Zhang; Zixin Deng; Shuangjun Lin
Journal:  Sci Rep       Date:  2016-02-05       Impact factor: 4.379

7.  Draft Genome Sequence of Streptomyces sp. B9173, a Producer of Indole Diketopiperazine Maremycins.

Authors:  Fang Luo; Yi Zou; Tingting Huang; Shuangjun Lin
Journal:  Genome Announc       Date:  2017-06-01
  7 in total

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