Literature DB >> 23866020

Biocatalytic synthesis of pikromycin, methymycin, neomethymycin, novamethymycin, and ketomethymycin.

Douglas A Hansen1, Christopher M Rath, Eli B Eisman, Alison R H Narayan, Jeffrey D Kittendorf, Jonathan D Mortison, Yeo Joon Yoon, David H Sherman.   

Abstract

A biocatalytic platform that employs the final two monomodular type I polyketide synthases of the pikromycin pathway in vitro followed by direct appendage of D-desosamine and final C-H oxidation(s) in vivo was developed and applied toward the synthesis of a suite of 12- and 14-membered ring macrolide natural products. This methodology delivered both compound classes in 13 steps (longest linear sequence) from commercially available (R)-Roche ester in >10% overall yields.

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Year:  2013        PMID： 23866020      PMCID： PMC3771335          DOI： 10.1021/ja404134f

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  40 in total

1.  Total synthesis of pikromycin.

Authors:  Hong-Se Oh; Han-Young Kang
Journal:  J Org Chem       Date:  2011-12-30       Impact factor: 4.354

2.  Efficient, chemoenzymatic process for manufacture of the Boceprevir bicyclic [3.1.0]proline intermediate based on amine oxidase-catalyzed desymmetrization.

Authors:  Tao Li; Jack Liang; Alexandre Ambrogelly; Tim Brennan; Guy Gloor; Gjalt Huisman; James Lalonde; Azzeddine Lekhal; Ben Mijts; Sheela Muley; Lisa Newman; Matt Tobin; George Wong; Aleksey Zaks; Xiyun Zhang
Journal:  J Am Chem Soc       Date:  2012-03-28       Impact factor: 15.419

Review 3.  Assembly-line enzymology for polyketide and nonribosomal Peptide antibiotics: logic, machinery, and mechanisms.

Authors:  Michael A Fischbach; Christopher T Walsh
Journal:  Chem Rev       Date:  2006-08       Impact factor: 60.622

4.  Preparation of L (+) beta-hydroxyisobutyric acid by bacterial oxidation of isobutyric acid.

Authors:  C T Goodhue; J R Schaeffer
Journal:  Biotechnol Bioeng       Date:  1971-03       Impact factor: 4.530

5.  Pseudoephenamine: a practical chiral auxiliary for asymmetric synthesis.

Authors:  Marvin R Morales; Kevin T Mellem; Andrew G Myers
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-27       Impact factor: 15.336

6.  Identification of DEBS 1, DEBS 2 and DEBS 3, the multienzyme polypeptides of the erythromycin-producing polyketide synthase from Saccharopolyspora erythraea.

Authors:  P Caffrey; D J Bevitt; J Staunton; P F Leadlay
Journal:  FEBS Lett       Date:  1992-06-15       Impact factor: 4.124

7.  Biochemical investigation of pikromycin biosynthesis employing native penta- and hexaketide chain elongation intermediates.

Authors:  Courtney C Aldrich; Brian J Beck; Robert A Fecik; David H Sherman
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

8.  Total synthesis of 10-deoxymethynolide and narbonolide.

Authors:  Richeng Xuan; Hong-Se Oh; Younghoon Lee; Han-Young Kang
Journal:  J Org Chem       Date:  2008-01-19       Impact factor: 4.354

9.  Development of an efficient, scalable, aldolase-catalyzed process for enantioselective synthesis of statin intermediates.

Authors:  William A Greenberg; Alexander Varvak; Sarah R Hanson; Kelvin Wong; Hongjun Huang; Pei Chen; Mark J Burk
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-06       Impact factor: 11.205

10.  The methymycin/pikromycin pathway: a model for metabolic diversity in natural product biosynthesis.

Authors:  Jeffrey D Kittendorf; David H Sherman
Journal:  Bioorg Med Chem       Date:  2008-11-05       Impact factor: 3.641
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  26 in total

1.  Development of a Genetically Encoded Biosensor for Detection of Polyketide Synthase Extender Units in Escherichia coli.

Authors:  Edward Kalkreuter; Aaron M Keeler; Alexandra A Malico; Kyle S Bingham; Anuran K Gayen; Gavin J Williams
Journal:  ACS Synth Biol       Date:  2019-05-28       Impact factor: 5.110

2.  Probing Selectivity and Creating Structural Diversity Through Hybrid Polyketide Synthases.

Authors:  Aaron A Koch; Jennifer J Schmidt; Andrew N Lowell; Douglas A Hansen; Katherine M Coburn; Joseph A Chemler; David H Sherman
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-05       Impact factor: 15.336

3.  Use of a biosynthetic intermediate to explore the chemical diversity of pseudo-natural fungal polyketides.

Authors:  Teigo Asai; Kento Tsukada; Satomi Ise; Naoki Shirata; Makoto Hashimoto; Isao Fujii; Katsuya Gomi; Kosuke Nakagawara; Eiichi N Kodama; Yoshiteru Oshima
Journal:  Nat Chem       Date:  2015-08-03       Impact factor: 24.427

4.  Biosynthetic Cyclization Catalysts for the Assembly of Peptide and Polyketide Natural Products.

Authors:  Maria L Adrover-Castellano; Jennifer J Schmidt; David H Sherman
Journal:  ChemCatChem       Date:  2021-01-28       Impact factor: 5.686

5.  Resistance to ketolide antibiotics by coordinated expression of rRNA methyltransferases in a bacterial producer of natural ketolides.

Authors:  Mashal M Almutairi; Sung Ryeol Park; Simon Rose; Douglas A Hansen; Nora Vázquez-Laslop; Stephen Douthwaite; David H Sherman; Alexander S Mankin
Journal:  Proc Natl Acad Sci U S A       Date:  2015-10-05       Impact factor: 11.205

6.  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

7.  Chemoenzymatic Total Synthesis and Structural Diversification of Tylactone-Based Macrolide Antibiotics through Late-Stage Polyketide Assembly, Tailoring, and C-H Functionalization.

Authors:  Andrew N Lowell; Matthew D DeMars; Samuel T Slocum; Fengan Yu; Krithika Anand; Joseph A Chemler; Nisha Korakavi; Jennifer K Priessnitz; Sung Ryeol Park; Aaron A Koch; Pamela J Schultz; David H Sherman
Journal:  J Am Chem Soc       Date:  2017-06-05       Impact factor: 15.419

8.  Inversion of Extender Unit Selectivity in the Erythromycin Polyketide Synthase by Acyltransferase Domain Engineering.

Authors:  Irina Koryakina; Christian Kasey; John B McArthur; Andrew N Lowell; Joseph A Chemler; Shasha Li; Douglas A Hansen; David H Sherman; Gavin J Williams
Journal:  ACS Chem Biol       Date:  2016-11-29       Impact factor: 5.100

9.  Investigating the reactivities of a polyketide synthase module through fluorescent click chemistry.

Authors:  Amanda Jane Hughes; Matthew R Tibby; Drew T Wagner; Johnathan N Brantley; Adrian T Keatinge-Clay
Journal:  Chem Commun (Camb)       Date:  2013-11-06       Impact factor: 6.222

10.  Evolution of Efficient Modular Polyketide Synthases by Homologous Recombination.

Authors:  Joseph A Chemler; Ashootosh Tripathi; Douglas A Hansen; Mark O'Neil-Johnson; Russell B Williams; Courtney Starks; Sung Ryeol Park; David H Sherman
Journal:  J Am Chem Soc       Date:  2015-08-13       Impact factor: 15.419
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