Intermediates Released from a Polyether-Producing Polyketide Synthase Provide Insight into the Mechanism of Oxidative Cyclization

Stereochemistry resolved: The introduction of hybrid polyketide synthases in Streptomyces cinnamonensis has shown that the E forms of a tetraketide and pentaketide are intermediates in the biosynthesis of the antibiotic ionophore monensin A (see structure). Furthermore, the trans double bond present...

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Published inAngewandte Chemie (International ed.) Vol. 42; no. 37; pp. 4475 - 4478
Main Authors Hughes-Thomas, Zoë A., Stark, Christian B. W., Böhm, Ines U., Staunton, James, Leadlay, Peter F.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 29.09.2003
WILEY‐VCH Verlag
Wiley
Subjects
antibiotics
Chemistry
Chemistry, Multidisciplinary
configuration determination
Cyclization
Ionophores - chemistry
Ionophores - metabolism
Molecular Structure
Monensin - biosynthesis
Monensin - chemistry
Multienzyme Complexes - metabolism
natural products
oxidation
Oxidation-Reduction
Physical Sciences
polyethers
Science & Technology
DOMAIN
SPECIFICITY
MODE
oxidation
configuration determination
MONENSIN BIOSYNTHETIC-PATHWAY
natural products
polyethers
ORIGIN
THIOESTERASE
OXYGEN-ATOMS
antibiotics
MOLECULAR-OXYGEN
POLYCYCLIZATION
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Summary:Stereochemistry resolved: The introduction of hybrid polyketide synthases in Streptomyces cinnamonensis has shown that the E forms of a tetraketide and pentaketide are intermediates in the biosynthesis of the antibiotic ionophore monensin A (see structure). Furthermore, the trans double bond present in these intermediates has been identified as one of the targets for the epoxidase that initiates oxidative cyclization.
Bibliography:istex:553F9D306146211B2073ABFE3EE631D22C16FB99
ArticleID:ANIE200351375
ark:/67375/WNG-26ZDGSND-7
This research was supported by the Biotechnology and Biological Sciences Research Council (BBSRC). We gratefully acknowledge the support of a studentship from the BBSRC (to Z.A.H.-T.), the support of I.U.B. through a grant from Glaxo Group Research, Stevenage, UK (to P.F.L. and J.S.), and a grant from Roche Pharmaceuticals (Basel) and an EU Marie Curie Postdoctoral Training Fellowship (to C.B.W.S.).
This research was supported by the Biotechnology and Biological Sciences Research Council (BBSRC). We gratefully acknowledge the support of a studentship from the BBSRC (to Z.A.H.‐T.), the support of I.U.B. through a grant from Glaxo Group Research, Stevenage, UK (to P.F.L. and J.S.), and a grant from Roche Pharmaceuticals (Basel) and an EU Marie Curie Postdoctoral Training Fellowship (to C.B.W.S.).
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200351375