Literature DB >> 15070349

The dynamic structure of jadomycin B and the amino acid incorporation step of its biosynthesis.

Uwe Rix1, Jianting Zheng, Lily L Remsing Rix, Lisa Greenwell, Keqian Yang, Jürgen Rohr.   

Abstract

Jadomycin B, an antifungal antibiotic with a unique 8H-benz[b]oxazolo[3,2-f]phenanthridine pentacyclic skeleton produced by the bacterium Streptomyces venezuelae ISP 5230, exists in a dynamic equilibrium of two diastereomers differing in the configuration of C-3a. Several novel jadomycins with various amino acid-derived 1-side chains could be generated, by replacing isoleucine in the production medium of S. venezuelae with other amino acids. These two findings led to the conclusion that a nonenzymatic reaction with the amino acid followed by a likewise nonenzymatic cyclization cascade are crucial for its late biosynthesis.

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Year:  2004        PMID: 15070349     DOI: 10.1021/ja031724o

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


  19 in total

1.  Cytotoxic activities of new jadomycin derivatives.

Authors:  Jian-Ting Zheng; Uwe Rix; Lixia Zhao; Cynthia Mattingly; Val Adams; Quan Chen; Jürgen Rohr; Ke-Qian Yang
Journal:  J Antibiot (Tokyo)       Date:  2005-06       Impact factor: 2.649

2.  Culture conditions improving the production of jadomycin B.

Authors:  David L Jakeman; Cathy L Graham; Wendy Young; Leo C Vining
Journal:  J Ind Microbiol Biotechnol       Date:  2006-03-28       Impact factor: 3.346

3.  Multi-oxygenase complexes of the gilvocarcin and jadomycin biosyntheses.

Authors:  Madan K Kharel; Lili Zhu; Tao Liu; Jürgen Rohr
Journal:  J Am Chem Soc       Date:  2007-03-09       Impact factor: 15.419

4.  Antimicrobial activities of jadomycin B and structurally related analogues.

Authors:  David L Jakeman; Srinivasulu Bandi; Cathy L Graham; Taryn R Reid; Jason R Wentzell; Susan E Douglas
Journal:  Antimicrob Agents Chemother       Date:  2008-12-15       Impact factor: 5.191

5.  Production of Stealthin C Involves an S-N-Type Smiles Rearrangement.

Authors:  Peng Wang; Gloria J Hong; Matthew R Wilson; Emily P Balskus
Journal:  J Am Chem Soc       Date:  2017-02-16       Impact factor: 15.419

6.  Functional analyses of oxygenases in jadomycin biosynthesis and identification of JadH as a bifunctional oxygenase/dehydrase.

Authors:  Yi-Hua Chen; Chen-Chen Wang; Lisa Greenwell; Uwe Rix; Dirk Hoffmeister; Leo C Vining; Jürgen Rohr; Ke-Qian Yang
Journal:  J Biol Chem       Date:  2005-04-06       Impact factor: 5.157

Review 7.  A comprehensive review of glycosylated bacterial natural products.

Authors:  Sherif I Elshahawi; Khaled A Shaaban; Madan K Kharel; Jon S Thorson
Journal:  Chem Soc Rev       Date:  2015-11-07       Impact factor: 54.564

Review 8.  Chalkophores.

Authors:  Grace E Kenney; Amy C Rosenzweig
Journal:  Annu Rev Biochem       Date:  2018-04-18       Impact factor: 23.643

9.  Elucidation of oxygenation steps during oviedomycin biosynthesis and generation of derivatives with increased antitumor activity.

Authors:  Felipe Lombó; Mohamed S Abdelfattah; Alfredo F Braña; José A Salas; Jürgen Rohr; Carmen Méndez
Journal:  Chembiochem       Date:  2009-01-26       Impact factor: 3.164

10.  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

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