Literature DB >> 22807264

Precursor-directed syntheses and biological evaluation of new elansolid derivatives.

Heinrich Steinmetz1, Wiebke Zander, Muftah A M Shushni, Rolf Jansen, Klaus Gerth, Richard Dehn, Gerald Dräger, Andreas Kirschning, Rolf Müller.   

Abstract

The antibiotic elansolid C1 (8) was isolated from Chitinophaga sancti strain FxGBF13 after fermentation in the presence of anthranilic acid. Remarkably, 8 was also obtained by addition of anthranilic acid to a crude fermentation extract containing the macrolide elansolid A2 (1*). This Michael-type conjugate addition allowed us to generate 21 new derivatives of elansolid C1 (9-29) by using various nucleophiles. Biological activities of all derivatives were evaluated against Staphylococcus aureus, Micrococcus luteus, and the mouse cell line L929.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 22807264     DOI： 10.1002/cbic.201200228

Source DB:  PubMed          Journal:  Chembiochem        ISSN： 1439-4227            Impact factor:   3.164


  9 in total

1.  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

2.  Precursor-Directed Generation of Amidine Containing Ammosamide Analogs: Ammosamides E-P.

Authors:  Ende Pan; Nathaniel W Oswald; Aaron G Legako; Janie M Life; Bruce A Posner; John B Macmillan
Journal:  Chem Sci       Date:  2013-01       Impact factor: 9.825

3.  Discoipyrroles A-D: isolation, structure determination, and synthesis of potent migration inhibitors from Bacillus hunanensis.

Authors:  Youcai Hu; Malia B Potts; Dominic Colosimo; Mireya L Herrera-Herrera; Aaron G Legako; Muhammed Yousufuddin; Michael A White; John B MacMillan
Journal:  J Am Chem Soc       Date:  2013-08-28       Impact factor: 15.419

4.  Discovery, Characterization, and Analogue Synthesis of Bohemamine Dimers Generated by Non-enzymatic Biosynthesis.

Authors:  Peng Fu; Aaron Legako; Scott La; John B MacMillan
Journal:  Chemistry       Date:  2016-02-02       Impact factor: 5.236

5.  Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids.

Authors:  Yijun Yan; Jing Yang; Zhiyin Yu; Mingming Yu; Ya-Tuan Ma; Li Wang; Can Su; Jianying Luo; Geoffrey P Horsman; Sheng-Xiong Huang
Journal:  Nat Commun       Date:  2016-10-07       Impact factor: 14.919

6.  Total synthesis of elansolids B1 and B2.

Authors:  Liang-Liang Wang; Andreas Kirschning
Journal:  Beilstein J Org Chem       Date:  2017-06-28       Impact factor: 2.883

7.  Optimization of the biotechnological production of a novel class of anti-MRSA antibiotics from Chitinophaga sancti.

Authors:  Amelie Beckmann; Stephan Hüttel; Viktoria Schmitt; Rolf Müller; Marc Stadler
Journal:  Microb Cell Fact       Date:  2017-08-17       Impact factor: 5.328

8.  Molecular basis of dimer formation during the biosynthesis of benzofluorene-containing atypical angucyclines.

Authors:  Chunshuai Huang; Chunfang Yang; Wenjun Zhang; Liping Zhang; Bidhan Chandra De; Yiguang Zhu; Xiaodong Jiang; Chunyan Fang; Qingbo Zhang; Cheng-Shan Yuan; Hung-Wen Liu; Changsheng Zhang
Journal:  Nat Commun       Date:  2018-05-25       Impact factor: 14.919

9.  Detailed Mechanistic Study of the Non-enzymatic Formation of the Discoipyrrole Family of Natural Products.

Authors:  Dominic A Colosimo; John B MacMillan
Journal:  J Am Chem Soc       Date:  2016-02-11       Impact factor: 15.419
  9 in total

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