ArticleBeilstein journal of organic chemistry2019
Inherent atomic mobility changes in carbocation intermediates during the sesterterpene cyclization cascade.
Article in Beilstein journal of organic chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Research Progress on Fungal Sesterterpenoids Biosynthesis.Journal of fungi (Basel, Switzerland) · 2022Review
- Enantioselective Tail-to-Head Cyclizations Catalyzed by Dual-Hydrogen-Bond Donors.Journal of the American Chemical Society · 2020Article
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5 authors.
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Abstract
We previously showed that the regio- and stereoselectivity in terpene-forming reactions are determined by the conformations of the carbocation intermediates, which reflect the initial conformation of the substrate, geranylfarnesyl diphosphate (GFPP). However, it remains unclear how the initial conformation of GFPP is controlled, and which part(s) of the GFPP molecule are important for its fixation inside the substrate-binding pocket. Here, we present the first detailed analysis of the inherent atomic mobility in carbocation intermediates during sesterterpene biosynthesis. We identified two methyl groups as the least mobile of all the carbons of the carbocation intermediates in the first half of the cyclization cascade. Our analysis suggests that these two methyl groups are critical for the preorganization of GFPP in the biosynthetic pathways leading to sesterfisherol and quiannulatene.
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