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Pyran Formation by an Atypical CYP‐Mediated Four‐Electron Oxygenation–Cyclization Cascade in an Engineered Aureothin Pathway
Author(s) -
Richter Martin,
Busch Benjamin,
Ishida Keishi,
Moore Bradley S.,
Hertweck Christian
Publication year - 2012
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201200406
Subject(s) - pyran , polyketide , chemistry , stereochemistry , ring (chemistry) , combinatorial chemistry , computer science , computational biology , biochemistry , biology , enzyme , biosynthesis , organic chemistry
Small changes, big effect: A new aureothin derivative, aureopyran, which features an unusual pyran backbone, was generated by simply altering the enzymatic methylation topology. The α‐pyrone ring hampers the correct placement of the polyketide backbone in the multifunctional cytochrome P450 monooxygenase AurH. Instead of a tetrahydrofuran ring, an oxo intermediate is formed that readily undergoes a rare electrocyclization reaction.