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Cover Feature: Flavin‐Dependent Monooxygenases NotI and NotI′ Mediate Spiro‐Oxindole Formation in Biosynthesis of the Notoamides (ChemBioChem 17/2020)
Author(s) -
Fraley Amy E.,
Tran Hong T.,
Kelly Samantha P.,
Newmister Sean A.,
Tripathi Ashootosh,
Kato Hikaru,
Tsukamoto Sachiko,
Du Lei,
Li Shengying,
Williams Robert M.,
Sherman David H.
Publication year - 2020
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.202000548
Subject(s) - oxindole , monooxygenase , chemistry , enantiomer , stereochemistry , enzyme , biosynthesis , cyclohexane , biochemistry , organic chemistry , catalysis , cytochrome p450
The notoamides are a fascinating class of anticancer natural products where two phylogenetically related fungal strains have evolved to generate enantiomeric (mirror image) terminal products. A study of the enzymes (NotI/NotI′) responsible for spirocycle formation revealed their differential flexibility in accepting the opposite substrate and catalyzing formation of the respective spiro‐oxindole product. The preferential conversion of (−)‐stephacidin A by both enzymes suggests an evolutionary divergence from a common ancestor that was selective for (+)‐notoamide B/A production. More information can be found in the full paper by R. M. Williams, D. H. Sherman, et al.