Cyclization of (−)-Pregaliellalactone in the Fungus Galiella rufa

An intramolecular Diels–Alder reaction with inverse electron demand in a polyketide biosynthetic pathway is reported in which the rate of the cyclization is enhanced in vivo. Alive mycelia of the fungus Galiella rufa catalyze the cyclization of (−)‐pregaliellalactone (1) to (+)‐desoxygaliellalactone...

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Published inAngewandte Chemie International Edition Vol. 41; no. 12; pp. 2158 - 2160
Main Authors Johansson, Martin, Köpcke, Bärbel, Anke, Heidrun, Sterner, Olov
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 17.06.2002
WILEY‐VCH Verlag GmbH
Wiley
Subjects
Ascomycota - chemistry
biosynthesis
Chemical Sciences
Chemistry
Chemistry, Multidisciplinary
Cyclization
cycloaddition
enzyme catalysis
Kemi
Lactones - chemistry
Molecular Structure
natural products
Natural Sciences
Naturvetenskap
Physical Sciences
Science & Technology
SYNTHASE
natural products
enzyme catalysis
cycloaddition
biosynthesis
DIELS-ALDER REACTION
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Summary:An intramolecular Diels–Alder reaction with inverse electron demand in a polyketide biosynthetic pathway is reported in which the rate of the cyclization is enhanced in vivo. Alive mycelia of the fungus Galiella rufa catalyze the cyclization of (−)‐pregaliellalactone (1) to (+)‐desoxygaliellalactone (2), while dead mycelia have no effect. No rate increase was observed with the unnatural enantiomer (+)‐1.
Bibliography:istex:A6E444F6BA5C70C0038D1D4537345A2F71719B44
ark:/67375/WNG-ZCVKMMQC-6
ArticleID:ANIE2158
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/1521-3773(20020617)41:12<2158::AID-ANIE2158>3.0.CO;2-P