Literature DB >> 22519860

6-Deoxyerythronolide B synthase thioesterase-catalyzed macrocyclization is highly stereoselective.

Atahualpa Pinto1, Meng Wang, Mark Horsman, Christopher N Boddy.   

Abstract

Macrocyclic polyketide natural products are an indispensable source of therapeutic agents. The final stage of their biosynthesis, macrocyclization, is catalyzed regio- and stereoselectively by a thioesterase. A panel of substrates were synthesized to test their specificity for macrocyclization by the erythromycin polyketide synthase TE (DEBS TE) in vitro. It was shown that DEBS TE is highly stereospecific, successfully macrocyclizing a 14-member ring substrate with an R configured O-nucleophile, and highly regioselective, generating exclusively the 14-member lactone over the 12-member lactone.

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Year:  2012        PMID： 22519860     DOI： 10.1021/ol300707j

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


  10 in total

1.  Identification of a Thioesterase Bottleneck in the Pikromycin Pathway through Full-Module Processing of Unnatural Pentaketides.

Authors:  Douglas A Hansen; Aaron A Koch; David H Sherman
Journal:  J Am Chem Soc       Date:  2017-09-19       Impact factor: 15.419

Review 2.  Engineering polyketide synthases and nonribosomal peptide synthetases.

Authors:  Gavin J Williams
Journal:  Curr Opin Struct Biol       Date:  2013-07-06       Impact factor: 6.809

3.  Microwave-assisted synthesis of macrocycles via intramolecular and/or bimolecular Ullmann coupling.

Authors:  Li Shen; Charles J Simmons; Dianqing Sun
Journal:  Tetrahedron Lett       Date:  2012-06-06       Impact factor: 2.415

4.  A Versatile Chemoenzymatic Synthesis for the Discovery of Potent Cryptophycin Analogs.

Authors:  Jennifer J Schmidt; Yogan Khatri; Scott I Brody; Catherine Zhu; Halina Pietraszkiewicz; Frederick A Valeriote; David H Sherman
Journal:  ACS Chem Biol       Date:  2020-02-03       Impact factor: 5.100

5.  Cross-linking of a polyketide synthase domain leads to a recyclable biocatalyst for chiral oxygen heterocycle synthesis.

Authors:  Lisa Wagner; Theresa Roß; Tim Hollmann; Frank Hahn
Journal:  RSC Adv       Date:  2021-06-07       Impact factor: 3.361

6.  Iterative Mechanism of Macrodiolide Formation in the Anticancer Compound Conglobatin.

Authors:  Yongjun Zhou; Annabel C Murphy; Markiyan Samborskyy; Patricia Prediger; Luiz Carlos Dias; Peter F Leadlay
Journal:  Chem Biol       Date:  2015-06-18

Review 7.  Engineered polyketides: Synergy between protein and host level engineering.

Authors:  Jesus F Barajas; Jacquelyn M Blake-Hedges; Constance B Bailey; Samuel Curran; Jay D Keasling
Journal:  Synth Syst Biotechnol       Date:  2017-09-07

8.  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

9.  Macrodiolide Formation by the Thioesterase of a Modular Polyketide Synthase.

Authors:  Yongjun Zhou; Patrícia Prediger; Luiz Carlos Dias; Annabel C Murphy; Peter F Leadlay
Journal:  Angew Chem Weinheim Bergstr Ger       Date:  2015-03-06

10.  Complete genome sequence of producer of the glycopeptide antibiotic Aculeximycin Kutzneria albida DSM 43870T, a representative of minor genus of Pseudonocardiaceae.

Authors:  Yuriy Rebets; Bogdan Tokovenko; Igor Lushchyk; Christian Rückert; Nestor Zaburannyi; Andreas Bechthold; Jörn Kalinowski; Andriy Luzhetskyy
Journal:  BMC Genomics       Date:  2014-10-10       Impact factor: 3.969
  10 in total

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