Literature DB >> 16249083

Macrolactonization to 10-deoxymethynolide catalyzed by the recombinant thioesterase of the picromycin/methymycin polyketide synthase.

Weiguo He1, Jiaquan Wu, Chaitan Khosla, David E Cane.   

Abstract

The recombinant thioesterase (TE) domain of the picromycin/methymycin synthase (PICS) catalyzes the macrolactonization of 3, the N-acetylcysteamine thioester of seco-10-deoxymethynolide to generate 10-deoxymethynolide (1) with high efficiency. By contrast, 4, the 7-dihydro derivative of seco-thioester 3, undergoes exclusive hydrolysis by PICS TE to seco-acid 5. The recombinant TE domain of 6-deoxyerythronolide B synthase (DEBS TE) shows the same reaction specificity as PICS TE, but with significantly lower activity.

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Year:  2005        PMID： 16249083     DOI： 10.1016/j.bmcl.2005.09.077

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  5 in total

Review 1.  Structural insights into nonribosomal peptide enzymatic assembly lines.

Authors:  Alexander Koglin; Christopher T Walsh
Journal:  Nat Prod Rep       Date:  2009-05-22       Impact factor: 13.423

Review 2.  The type I fatty acid and polyketide synthases: a tale of two megasynthases.

Authors:  Stuart Smith; Shiou-Chuan Tsai
Journal:  Nat Prod Rep       Date:  2007-07-02       Impact factor: 13.423

3.  A thioesterase from an iterative fungal polyketide synthase shows macrocyclization and cross coupling activity and may play a role in controlling iterative cycling through product offloading.

Authors:  Meng Wang; Hui Zhou; Monica Wirz; Yi Tang; Christopher N Boddy
Journal:  Biochemistry       Date:  2009-07-14       Impact factor: 3.162

4.  Mechanism of thioesterase-catalyzed chain release in the biosynthesis of the polyether antibiotic nanchangmycin.

Authors:  Tiangang Liu; Xin Lin; Xiufen Zhou; Zixin Deng; David E Cane
Journal:  Chem Biol       Date:  2008-05

5.  A Single Active Site Mutation in the Pikromycin Thioesterase Generates a More Effective Macrocyclization Catalyst.

Authors:  Aaron A Koch; Douglas A Hansen; Vikram V Shende; Lawrence R Furan; K N Houk; Gonzalo Jiménez-Osés; David H Sherman
Journal:  J Am Chem Soc       Date:  2017-09-19       Impact factor: 15.419
  5 in total

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