Literature DB >> 18503202

Guadinomines, Type III secretion system inhibitors, produced by Streptomyces sp. K01-0509. II: physico-chemical properties and structure elucidation.

Masato Iwatsuki1, Ryuji Uchida, Hitomi Yoshijima, Hideaki Ui, Kazuro Shiomi, Yong-Pil Kim, Tomoyasu Hirose, Toshiaki Sunazuka, Akio Abe, Hiroshi Tomoda, Satoshi Omura.   

Abstract

The structures of guadinomines, new inhibitors of a bacterial Type III secretion system produced by Streptomyces sp. K01-0509, were elucidated by spectroscopic studies including various NMR experiments. Guadinomines A, B, C(1), C(2) and D consist of a carbamoylated cyclic guanidinyl moiety, an alkyl chain moiety and an L-Ala-L-Val moiety in common, while guadinomic acid is a smaller molecule consisting of a carbamoylated cyclic guanidinyl moiety and a hydroxyl hexanoate moiety.

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Year:  2008        PMID: 18503202     DOI: 10.1038/ja.2008.33

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN: 0021-8820            Impact factor:   2.649


  15 in total

Review 1.  The re-emergence of natural products for drug discovery in the genomics era.

Authors:  Alan L Harvey; RuAngelie Edrada-Ebel; Ronald J Quinn
Journal:  Nat Rev Drug Discov       Date:  2015-01-23       Impact factor: 84.694

2.  Cladomarine, a new anti-saprolegniasis compound isolated from the deep-sea fungus, Penicillium coralligerum YK-247.

Authors:  Konami Takahashi; Kazunari Sakai; Yuriko Nagano; Sakiko Orui Sakaguchi; Andre O Lima; Vivian H Pellizari; Masato Iwatsuki; Kiyotaka Takishita; Kenichi Nonaka; Katsunori Fujikura; Satoshi Ōmura
Journal:  J Antibiot (Tokyo)       Date:  2017-05-31       Impact factor: 2.649

3.  Total Synthesis of (+)-Guadinomic Acid via Hydroxyl-Directed Guanidylation.

Authors:  Bradley T Reid; Artur K Mailyan; Armen Zakarian
Journal:  J Org Chem       Date:  2018-06-22       Impact factor: 4.354

4.  The bacterial type III secretion system as a target for developing new antibiotics.

Authors:  Andrew C McShan; Roberto N De Guzman
Journal:  Chem Biol Drug Des       Date:  2015-01       Impact factor: 2.817

5.  Molecular insights into the biosynthesis of guadinomine: a type III secretion system inhibitor.

Authors:  Tracy C Holmes; Aaron E May; Kathia Zaleta-Rivera; J Graham Ruby; Peter Skewes-Cox; Michael A Fischbach; Joseph L DeRisi; Masato Iwatsuki; Satoshi Ōmura; Chaitan Khosla
Journal:  J Am Chem Soc       Date:  2012-10-10       Impact factor: 15.419

6.  Stereoselective Synthesis of Isoxazolidines via Copper-Catalyzed Alkene Diamination.

Authors:  Zainab M Khoder; Christina E Wong; Sherry R Chemler
Journal:  ACS Catal       Date:  2017-06-15       Impact factor: 13.084

7.  Substituted 2-imino-5-arylidenethiazolidin-4-one inhibitors of bacterial type III secretion.

Authors:  Toni Kline; Heather B Felise; Kathleen C Barry; Stona R Jackson; Hai V Nguyen; Samuel I Miller
Journal:  J Med Chem       Date:  2008-11-27       Impact factor: 7.446

8.  Small molecules aimed at type III secretion systems to inhibit bacterial virulence.

Authors:  Lun K Tsou; Paul D Dossa; Howard C Hang
Journal:  Medchemcomm       Date:  2013-01-01       Impact factor: 3.597

9.  Small-molecule type III secretion system inhibitors block assembly of the Shigella type III secreton.

Authors:  Andreas K J Veenendaal; Charlotta Sundin; Ariel J Blocker
Journal:  J Bacteriol       Date:  2008-11-07       Impact factor: 3.490

10.  Isolation of Salmonella mutants resistant to the inhibitory effect of Salicylidene acylhydrazides on flagella-mediated motility.

Authors:  Isabel Martinez-Argudo; Andreas K J Veenendaal; Xia Liu; A Dorothea Roehrich; Maria C Ronessen; Giulia Franzoni; Katerine N van Rietschoten; Yusuke V Morimoto; Yumiko Saijo-Hamano; Matthew B Avison; David J Studholme; Keiichi Namba; Tohru Minamino; Ariel J Blocker
Journal:  PLoS One       Date:  2013-01-02       Impact factor: 3.240

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