Biosynthesis of Polycyclic Natural Products from Conjugated Polyenes via Tandem Isomerization and Pericyclic Reactions

We report biosynthetic pathways that can synthesize and transform conjugated octaenes and nonaenes to complex natural products. The biosynthesis of (−)-PF1018 involves an enzyme PfB that can control the regio-, stereo-, and periselectivity of multiple reactions starting from a conjugated octaene. Us...

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Published inJournal of the American Chemical Society Vol. 145; no. 25; pp. 13520 - 13525
Main Authors Niwa, Kanji, Ohashi, Masao, Xie, Kaili, Chiang, Chen-Yu, Jamieson, Cooper S., Sato, Michio, Watanabe, Kenji, Liu, Fang, Houk, K. N., Tang, Yi
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 28.06.2023
Subjects
Biological Products - metabolism
biosynthesis
Cyclization
enzymes
Isomerism
isomerization
lead
Polyenes
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Summary:We report biosynthetic pathways that can synthesize and transform conjugated octaenes and nonaenes to complex natural products. The biosynthesis of (−)-PF1018 involves an enzyme PfB that can control the regio-, stereo-, and periselectivity of multiple reactions starting from a conjugated octaene. Using PfB as a lead, we discovered a homologous enzyme, BruB, that facilitates diene isomerization, tandem 8π-6π-electrocyclization, and a 1,2-divinylcyclobutane Cope rearrangement to generate a new-to-nature compound.
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.3c02380