Literature DB >> 31799975

General chemoenzymatic route to two-stereocenter triketides employing assembly line ketoreductases.

Zhicheng Zhang1, Alexis J Cepeda, Mireya L Robles, Melissa Hirsch, Kaan Kumru, Jina A Zhou, Adrian T Keatinge-Clay.   

Abstract

Modular polyketide synthases (PKSs) are enzymatic assembly lines that fuse carbon fragments into complex chiral products. Here, their synthetic logic is employed to chemoenzymatically generate two-stereocenter triketides. Each of the four stereoisomers was constructed in a stereocontrolled manner using C-acylation and two PKS ketoreductases possessing opposite stereoselectivities.

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Year:  2019        PMID: 31799975      PMCID: PMC7172026          DOI: 10.1039/c9cc07966a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  22 in total

Review 1.  Biosynthesis of polyketides by trans-AT polyketide synthases.

Authors:  Jörn Piel
Journal:  Nat Prod Rep       Date:  2010-05-12       Impact factor: 13.423

Review 2.  Biosynthesis of polyketides by trans-AT polyketide synthases.

Authors:  Eric J N Helfrich; Jörn Piel
Journal:  Nat Prod Rep       Date:  2016-02       Impact factor: 13.423

Review 3.  Combinatorial biosynthesis of reduced polyketides.

Authors:  Kira J Weissman; Peter F Leadlay
Journal:  Nat Rev Microbiol       Date:  2005-12       Impact factor: 60.633

Review 4.  The Uncommon Enzymology of Cis-Acyltransferase Assembly Lines.

Authors:  Adrian T Keatinge-Clay
Journal:  Chem Rev       Date:  2017-04-10       Impact factor: 60.622

5.  Stereodiverse Iterative Synthesis of 1,3-Polyol Arrays through Asymmetric Catalytic Hydrogenation. Formal Total Synthesis of (-)-Cyanolide A.

Authors:  Wen Che; Yu-Zhen Li; Jin-Chi Liu; Shou-Fei Zhu; Jian-Hua Xie; Qi-Lin Zhou
Journal:  Org Lett       Date:  2019-03-18       Impact factor: 6.005

6.  A close look at a ketosynthase from a trans-acyltransferase modular polyketide synthase.

Authors:  Darren C Gay; Glen Gay; Abram J Axelrod; Matthew Jenner; Christoph Kohlhaas; Annette Kampa; Neil J Oldham; Jörn Piel; Adrian T Keatinge-Clay
Journal:  Structure       Date:  2014-02-06       Impact factor: 5.006

7.  A tylosin ketoreductase reveals how chirality is determined in polyketides.

Authors:  Adrian T Keatinge-Clay
Journal:  Chem Biol       Date:  2007-08

8.  Structural Basis of Polyketide Synthase O-Methylation.

Authors:  Meredith A Skiba; Marissa M Bivins; John R Schultz; Steffen M Bernard; William D Fiers; Qingyun Dan; Sarang Kulkarni; Peter Wipf; William H Gerwick; David H Sherman; Courtney C Aldrich; Janet L Smith
Journal:  ACS Chem Biol       Date:  2018-12-03       Impact factor: 5.100

9.  A model of structure and catalysis for ketoreductase domains in modular polyketide synthases.

Authors:  Ralph Reid; Misty Piagentini; Eduardo Rodriguez; Gary Ashley; Nina Viswanathan; John Carney; Daniel V Santi; C Richard Hutchinson; Robert McDaniel
Journal:  Biochemistry       Date:  2003-01-14       Impact factor: 3.162

Review 10.  Stereocontrol within polyketide assembly lines.

Authors:  Adrian T Keatinge-Clay
Journal:  Nat Prod Rep       Date:  2016-02       Impact factor: 13.423

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