A Sweet Origin for the Key Congocidine Precursor 4-Acetamidopyrrole-2-carboxylate

Feeding (Streptomyces) frenzy: Natural products belonging to the pyrrolamide family are defined by their pyrrole‐2‐carboxamide moiety. 4‐acetamidopyrrole‐2‐carboxylate is identified as the key pyrrolamide congocidine precursor (see scheme) through feeding studies using Streptomyces ambofaciens. The...

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Published inAngewandte Chemie (International ed.) Vol. 51; no. 30; pp. 7454 - 7458
Main Authors Lautru, Sylvie, Song, Lijiang, Demange, Luc, Lombès, Thomas, Galons, Hervé, Challis, Gregory L., Pernodet, Jean-Luc
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 23.07.2012
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Wiley-VCH Verlag
EditionInternational ed. in English
Subjects
Amides - chemistry
Amides - metabolism
Bacteriology
Biological Products - chemistry
Biological Products - metabolism
biosynthesis
Carbohydrates
Chemistry
Chemistry, Multidisciplinary
congocidine
Enzymes
Feeding
Life Sciences
Microbiology and Parasitology
Natural products
Netropsin - chemistry
Netropsin - metabolism
Origins
Pathways
Physical Sciences
Precursors
pyrrolamide
pyrrole
Pyrroles - chemical synthesis
Pyrroles - metabolism
Science & Technology
Streptomyces - chemistry
Streptomyces - enzymology
Streptomyces - metabolism
Sweets
SMALL MOLECULES
ESCHERICHIA-COLI
congocidine
COUMERMYCIN A
pyrrole
natural products
BIOSYNTHETIC GENE-CLUSTER
PSEUDOMONAS-FLUORESCENS
pyrrolamide
STREPTOMYCES-COELICOLOR PATHWAY
biosynthesis
UDP-N-ACETYLGLUCOSAMINE
INTERMEDIATE
PYRROLE MOIETY
METHYLENOMYCIN
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Summary:Feeding (Streptomyces) frenzy: Natural products belonging to the pyrrolamide family are defined by their pyrrole‐2‐carboxamide moiety. 4‐acetamidopyrrole‐2‐carboxylate is identified as the key pyrrolamide congocidine precursor (see scheme) through feeding studies using Streptomyces ambofaciens. The biosynthetic pathway of congocidine starts with the carbohydrate N‐acetylglucosamine and involves carbohydrate‐processing enzymes.
Bibliography:Pôle de Recherche et d'Enseignement Supérieur UniverSud Paris
European Union - No. CT-2004-0005224; No. CT-2005-029154
ArticleID:ANIE201201445
We would like to thank Dr. Christophe Corre for helpful discussions, Dr. Laurent Micouin for his help with the synthesis of the 4-acetamidopyrrole-2-methanol, and Dr. Cyrille Kouklovsky, Géraldine Le Goff, and Dr. Robert Thaï for their help with mass spectrometry. This work was supported in part by the European Union through the Integrated Project ActinoGEN (CT-2004-0005224) and the reintegration grant BOPA (CT-2005-029154), by the Pôle de Recherche et d'Enseignement Supérieur UniverSud Paris and by the Bettencourt Schueller Foundation.
Bettencourt Schueller Foundation
ark:/67375/WNG-T7VD2GKK-N
istex:32AB189D044B2BCA1E4B724A31E05BB7DDA556DF
We would like to thank Dr. Christophe Corre for helpful discussions, Dr. Laurent Micouin for his help with the synthesis of the 4‐acetamidopyrrole‐2‐methanol, and Dr. Cyrille Kouklovsky, Géraldine Le Goff, and Dr. Robert Thaï for their help with mass spectrometry. This work was supported in part by the European Union through the Integrated Project ActinoGEN (CT‐2004‐0005224) and the reintegration grant BOPA (CT‐2005‐029154), by the Pôle de Recherche et d’Enseignement Supérieur UniverSud Paris and by the Bettencourt Schueller Foundation.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201201445