Literature DB >> 28989201

Identification of an unexpected shunt pathway product provides new insights into tirandamycin biosynthesis.

Xingwang Zhang1, Zhong Li1,2, Lei Du1,2, George E Chlipala3, Patricia C Lopez3, Wei Zhang1, David H Sherman3, Shengying Li1.   

Abstract

Tirandamycin K (7), the first linear 7,13;9,13-diseco-tirandamycin derivative, was isolated from the tamI (encoding the TamI P450 monooxygenase) disruption mutant strain (ΔtamI) of marine Streptomyces sp. 307-9. Its chemical structure with relative and absolute configurations was elucidated by a combination of extensive spectroscopic analyses and biosynthetic inferences. Structural elucidation of this unusual compound provides new insights into tirandamycin biosynthesis. Moreover, examination of the biological activity of 7 confirms the essential function of the bicyclic ketal ring for antibiotic activities of tirandamycins.

Entities:  

Keywords:  Biosynthesis; Natural product; Streptomyces; Tetramic acid; Tirandamycin

Year:  2016        PMID： 28989201      PMCID： PMC5628624          DOI： 10.1016/j.tetlet.2016.11.080

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  22 in total

1.  Deciphering biosynthesis of the RNA polymerase inhibitor streptolydigin and generation of glycosylated derivatives.

Authors:  Carlos Olano; Cristina Gómez; María Pérez; Martina Palomino; Antonio Pineda-Lucena; Rodrigo J Carbajo; Alfredo F Braña; Carmen Méndez; José A Salas
Journal:  Chem Biol       Date:  2009-10-30

2.  Dihydromaltophilin; a novel fungicidal tetramic acid containing metabolite from Streptomyces sp.

Authors:  P R Graupner; S Thornburgh; J T Mathieson; E L Chapin; G M Kemmitt; J M Brown; C E Snipes
Journal:  J Antibiot (Tokyo)       Date:  1997-12       Impact factor: 2.649

3.  The structure of a ketoreductase determines the organization of the beta-carbon processing enzymes of modular polyketide synthases.

Authors:  Adrian T Keatinge-Clay; Robert M Stroud
Journal:  Structure       Date:  2006-03-23       Impact factor: 5.006

4.  Characterization of TrdL as a 10-hydroxy dehydrogenase and generation of new analogues from a tirandamycin biosynthetic pathway.

Authors:  Xuhua Mo; Hongbo Huang; Junying Ma; Zhongwen Wang; Bo Wang; Si Zhang; Changsheng Zhang; Jianhua Ju
Journal:  Org Lett       Date:  2011-04-01       Impact factor: 6.005

5.  Tirandamycins from Streptomyces sp. 17944 inhibiting the parasite Brugia malayi asparagine tRNA synthetase.

Authors:  Zhiguo Yu; Sanja Vodanovic-Jankovic; Nathan Ledeboer; Sheng-Xiong Huang; Scott R Rajski; Michael Kron; Ben Shen
Journal:  Org Lett       Date:  2011-03-15       Impact factor: 6.005

6.  Tirandamycin, an inhibitor of bacterial ribonucleic acid polymerase.

Authors:  F Reusser
Journal:  Antimicrob Agents Chemother       Date:  1976-10       Impact factor: 5.191

7.  Defining the mode of action of tetramic acid antibacterials derived from Pseudomonas aeruginosa quorum sensing signals.

Authors:  Colin A Lowery; Junguk Park; Christian Gloeckner; Michael M Meijler; Ryan S Mueller; Helena I Boshoff; Ricky L Ulrich; Clifton E Barry; Douglas H Bartlett; Vladimir V Kravchenko; Gunnar F Kaufmann; Kim D Janda
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

8.  Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation.

Authors:  Steven Tuske; Stefan G Sarafianos; Xinyue Wang; Brian Hudson; Elena Sineva; Jayanta Mukhopadhyay; Jens J Birktoft; Olivier Leroy; Sajida Ismail; Arthur D Clark; Chhaya Dharia; Andrew Napoli; Oleg Laptenko; Jookyung Lee; Sergei Borukhov; Richard H Ebright; Eddy Arnold
Journal:  Cell       Date:  2005-08-26       Impact factor: 41.582

9.  Medium optimization of Streptomyces sp. 17944 for tirandamycin B production and isolation and structural elucidation of tirandamycins H, I and J.

Authors:  Mostafa E Rateb; Zhiguo Yu; Yijun Yan; Dong Yang; Tingting Huang; Sanja Vodanovic-Jankovic; Michael A Kron; Ben Shen
Journal:  J Antibiot (Tokyo)       Date:  2013-05-29       Impact factor: 2.649
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  2 in total

1.  Identification of nocamycin biosynthetic gene cluster from Saccharothrix syringae NRRL B-16468 and generation of new nocamycin derivatives by manipulating gene cluster.

Authors:  Xuhua Mo; Chunrong Shi; Chun Gui; Yanjiao Zhang; Jianhua Ju; Qingji Wang
Journal:  Microb Cell Fact       Date:  2017-06-09       Impact factor: 5.328

Review 2.  The Biological and Chemical Diversity of Tetramic Acid Compounds from Marine-Derived Microorganisms.

Authors:  Minghua Jiang; Senhua Chen; Jing Li; Lan Liu
Journal:  Mar Drugs       Date:  2020-02-15       Impact factor: 5.118
  2 in total

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