Literature DB >> 25287333

Chemoenzymatic synthesis of spinosyn A.

Hak Joong Kim1, Sei-hyun Choi, Byung-sun Jeon, Namho Kim, Rongson Pongdee, Qingquan Wu, Hung-wen Liu.   

Abstract

Following the biosynthesis of polyketide backbones by polyketide synthases (PKSs), post-PKS modifications result in a significantly elevated level of structural complexity that renders the chemical synthesis of these natural products challenging. We report herein a total synthesis of the widely used polyketide insecticide spinosyn A by exploiting the prowess of both chemical and enzymatic methods. As more polyketide biosynthetic pathways are characterized, this chemoenzymatic approach is expected to become readily adaptable to streamlining the synthesis of other complex polyketides with more elaborate post-PKS modifications.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  biosynthesis; polyketide macrolides; post-polyketide synthase modifications; spinosyns; total synthesis

Mesh:

Substances:

Year:  2014        PMID: 25287333      PMCID: PMC4266379          DOI: 10.1002/anie.201407806

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


  24 in total

1.  Total synthesis of (-)-spinosyn A.

Authors:  Dustin J Mergott; Scott A Frank; William R Roush
Journal:  Proc Natl Acad Sci U S A       Date:  2004-06-01       Impact factor: 11.205

2.  The polyol domain of amphidinol 3. A stereoselective synthesis of the entire C(1)-C(30) sector.

Authors:  Leo A Paquette; Shuh-Kuen Chang
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

3.  In vitro characterization of the enzymes involved in TDP-D-forosamine biosynthesis in the spinosyn pathway of Saccharopolyspora spinosa.

Authors:  Lin Hong; Zongbao Zhao; Charles E Melançon; Hua Zhang; Hung-wen Liu
Journal:  J Am Chem Soc       Date:  2008-03-18       Impact factor: 15.419

4.  Molecular basis of Celmer's rules: stereochemistry of catalysis by isolated ketoreductase domains from modular polyketide synthases.

Authors:  Alexandros P Siskos; Abel Baerga-Ortiz; Shilpa Bali; Viktor Stein; Hassan Mamdani; Dieter Spiteller; Bojana Popovic; Jonathan B Spencer; James Staunton; Kira J Weissman; Peter F Leadlay
Journal:  Chem Biol       Date:  2005-10

5.  Biosynthesis of spinosyn in Saccharopolyspora spinosa: synthesis of permethylated rhamnose and characterization of the functions of SpnH, SpnI, and SpnK.

Authors:  Hak Joong Kim; Jess A White-Phillip; Yasushi Ogasawara; Nara Shin; Eta A Isiorho; Hung-Wen Liu
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

6.  Characterization of SpnQ from the spinosyn biosynthetic pathway of Saccharopolyspora spinosa: mechanistic and evolutionary implications for C-3 deoxygenation in deoxysugar biosynthesis.

Authors:  Lin Hong; Zongbao Zhao; Hung-wen Liu
Journal:  J Am Chem Soc       Date:  2006-11-08       Impact factor: 15.419

7.  The biosynthesis of spinosyn in Saccharopolyspora spinosa: synthesis of the cross-bridging precursor and identification of the function of SpnJ.

Authors:  Hak Joong Kim; Rongson Pongdee; Qingquan Wu; Lin Hong; Hung-wen Liu
Journal:  J Am Chem Soc       Date:  2007-11-07       Impact factor: 15.419

Review 8.  The biosynthetic logic of polyketide diversity.

Authors:  Christian Hertweck
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Improved procedure for the oxidative cleavage of olefins by OsO4-NaIO4.

Authors:  Wensheng Yu; Yan Mei; Ying Kang; Zhengmao Hua; Zhendong Jin
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

10.  Functional characterization and substrate specificity of spinosyn rhamnosyltransferase by in vitro reconstitution of spinosyn biosynthetic enzymes.

Authors:  Yi-Lin Chen; Yi-Hsine Chen; Yu-Chin Lin; Kuo-Chung Tsai; Hsien-Tai Chiu
Journal:  J Biol Chem       Date:  2009-01-06       Impact factor: 5.157

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  7 in total

Review 1.  Natural [4 + 2]-Cyclases.

Authors:  Byung-Sun Jeon; Shao-An Wang; Mark W Ruszczycky; Hung-Wen Liu
Journal:  Chem Rev       Date:  2016-12-01       Impact factor: 60.622

2.  Investigation of the mechanism of the SpnF-catalyzed [4+2]-cycloaddition reaction in the biosynthesis of spinosyn A.

Authors:  Byung-Sun Jeon; Mark W Ruszczycky; William K Russell; Geng-Min Lin; Namho Kim; Sei-Hyun Choi; Shao-An Wang; Yung-Nan Liu; John W Patrick; David H Russell; Hung-Wen Liu
Journal:  Proc Natl Acad Sci U S A       Date:  2017-09-05       Impact factor: 11.205

3.  Byproduct formation during the biosynthesis of spinosyn A and evidence for an enzymatic interplay to prevent its formation.

Authors:  Byung-Sun Jeon; Teng-Yi Huang; Mark W Ruszczycky; Sei-Hyun Choi; Namho Kim; Joseph Livy Franklin; Shang-Cheng Hung; Hung-Wen Liu
Journal:  Tetrahedron       Date:  2021-11-22       Impact factor: 2.388

4.  An unusual intramolecular trans-amidation.

Authors:  Heriberto Rivera; Sachin Dhar; James J La Clair; Shiou-Chuan Tsai; Michael D Burkart
Journal:  Tetrahedron       Date:  2016-06-23       Impact factor: 2.457

5.  Total Synthesis of (-)-Spinosyn A via Carbonylative Macrolactonization.

Authors:  Yu Bai; Xingyu Shen; Yong Li; Mingji Dai
Journal:  J Am Chem Soc       Date:  2016-08-17       Impact factor: 15.419

6.  The structure of SpnF, a standalone enzyme that catalyzes [4 + 2] cycloaddition.

Authors:  Christopher D Fage; Eta A Isiorho; Yungnan Liu; Drew T Wagner; Hung-wen Liu; Adrian T Keatinge-Clay
Journal:  Nat Chem Biol       Date:  2015-03-02       Impact factor: 15.040

7.  Computational Insights into an Enzyme-Catalyzed [4+2] Cycloaddition.

Authors:  Yiying Zheng; Walter Thiel
Journal:  J Org Chem       Date:  2017-11-29       Impact factor: 4.354

  7 in total

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