Biosynthesis of the Myxobacterial Antibiotic Corallopyronin A
Abstract Corallopyronin A is a myxobacterial compound with potent antibacterial activity. Feeding experiments with labelled precursors resulted in the deduction of all biosynthetic building blocks for corallopyronin A and revealed an unusual feature of this metabolite: its biosynthesis from two chai...
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crwiley:10.1002/cbic.201000085 2024-09-15T18:01:39+00:00 Biosynthesis of the Myxobacterial Antibiotic Corallopyronin A Erol, Özlem Schäberle, Till F. Schmitz, Alexander Rachid, Shwan Gurgui, Cristian El Omari, Mustafa Lohr, Friederike Kehraus, Stefan Piel, Jörn Müller, Rolf König, Gabriele M. 2010 http://dx.doi.org/10.1002/cbic.201000085 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcbic.201000085 https://onlinelibrary.wiley.com/doi/full/10.1002/cbic.201000085 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor ChemBioChem volume 11, issue 9, page 1253-1265 ISSN 1439-4227 1439-7633 journal-article 2010 crwiley https://doi.org/10.1002/cbic.201000085 2024-08-27T04:27:38Z Abstract Corallopyronin A is a myxobacterial compound with potent antibacterial activity. Feeding experiments with labelled precursors resulted in the deduction of all biosynthetic building blocks for corallopyronin A and revealed an unusual feature of this metabolite: its biosynthesis from two chains, one solely PKS‐derived and the other NRPS/PKS‐derived. The starter molecule is believed to be carbonic acid or its monomethyl ester. The putative corallopyronin A biosynthetic gene cluster is a trans‐AT‐type mixed PKS/NRPS gene cluster, containing a β‐branching cassette. Striking features of this gene cluster are a NRPS‐like adenylation domain that is part of a PKS‐type module and is believed to be responsible for glycine incorporation, as well as split modules with individual domains occurring on different genes. It is suggested that CorB is a trans‐acting ketosynthase and it is proposed that it catalyses the Claisen condensation responsible for the interconnection of the two chains. Additionally, the stereochemistry of corallopyronin A was deduced by a combination of a modified Mosher's method and ozonolysis with subsequent chiral GC analyses. Article in Journal/Newspaper Carbonic acid Wiley Online Library ChemBioChem 11 9 1253 1265 |
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Wiley Online Library |
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English |
description |
Abstract Corallopyronin A is a myxobacterial compound with potent antibacterial activity. Feeding experiments with labelled precursors resulted in the deduction of all biosynthetic building blocks for corallopyronin A and revealed an unusual feature of this metabolite: its biosynthesis from two chains, one solely PKS‐derived and the other NRPS/PKS‐derived. The starter molecule is believed to be carbonic acid or its monomethyl ester. The putative corallopyronin A biosynthetic gene cluster is a trans‐AT‐type mixed PKS/NRPS gene cluster, containing a β‐branching cassette. Striking features of this gene cluster are a NRPS‐like adenylation domain that is part of a PKS‐type module and is believed to be responsible for glycine incorporation, as well as split modules with individual domains occurring on different genes. It is suggested that CorB is a trans‐acting ketosynthase and it is proposed that it catalyses the Claisen condensation responsible for the interconnection of the two chains. Additionally, the stereochemistry of corallopyronin A was deduced by a combination of a modified Mosher's method and ozonolysis with subsequent chiral GC analyses. |
format |
Article in Journal/Newspaper |
author |
Erol, Özlem Schäberle, Till F. Schmitz, Alexander Rachid, Shwan Gurgui, Cristian El Omari, Mustafa Lohr, Friederike Kehraus, Stefan Piel, Jörn Müller, Rolf König, Gabriele M. |
spellingShingle |
Erol, Özlem Schäberle, Till F. Schmitz, Alexander Rachid, Shwan Gurgui, Cristian El Omari, Mustafa Lohr, Friederike Kehraus, Stefan Piel, Jörn Müller, Rolf König, Gabriele M. Biosynthesis of the Myxobacterial Antibiotic Corallopyronin A |
author_facet |
Erol, Özlem Schäberle, Till F. Schmitz, Alexander Rachid, Shwan Gurgui, Cristian El Omari, Mustafa Lohr, Friederike Kehraus, Stefan Piel, Jörn Müller, Rolf König, Gabriele M. |
author_sort |
Erol, Özlem |
title |
Biosynthesis of the Myxobacterial Antibiotic Corallopyronin A |
title_short |
Biosynthesis of the Myxobacterial Antibiotic Corallopyronin A |
title_full |
Biosynthesis of the Myxobacterial Antibiotic Corallopyronin A |
title_fullStr |
Biosynthesis of the Myxobacterial Antibiotic Corallopyronin A |
title_full_unstemmed |
Biosynthesis of the Myxobacterial Antibiotic Corallopyronin A |
title_sort |
biosynthesis of the myxobacterial antibiotic corallopyronin a |
publisher |
Wiley |
publishDate |
2010 |
url |
http://dx.doi.org/10.1002/cbic.201000085 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcbic.201000085 https://onlinelibrary.wiley.com/doi/full/10.1002/cbic.201000085 |
genre |
Carbonic acid |
genre_facet |
Carbonic acid |
op_source |
ChemBioChem volume 11, issue 9, page 1253-1265 ISSN 1439-4227 1439-7633 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/cbic.201000085 |
container_title |
ChemBioChem |
container_volume |
11 |
container_issue |
9 |
container_start_page |
1253 |
op_container_end_page |
1265 |
_version_ |
1810438749615554560 |