ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
1,2- or 1,3-Hydride Shifts: What Controls Guaiane Biosynthesis?
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 22 citations in OpenAlex.
- Article
- Mechanistic Characterisation and Engineering of Sesterviolene Synthase from Streptomyces violens.Angewandte Chemie (International ed. in English) · 2023Article
- Germacrene B - a central intermediate in sesquiterpene biosynthesis.Beilstein journal of organic chemistry · 2023Review
- Hedycaryol - Central Intermediates in Sesquiterpene Biosynthesis, Part II.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- The enzyme mechanism of patchoulol synthase.Beilstein journal of organic chemistry · 2022Article
- Functional Switch and Ethyl Group Formation in the Bacterial Polytrichastrene Synthase from Chryseobacterium polytrichastri.Angewandte Chemie (International ed. in English) · 2021Article
- 1,2- or 1,3-Hydride Shifts: What Controls Guaiane Biosynthesis?Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
Corrections and comments
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Authors and funding
3 authors at 2 institutions in 1 country.
Funding
Abstract
A systematic computational study addressing the entire chemical space of guaianes in conjunction with an analysis of all known compounds shows that 1,3-hydride shifts are rare events in guaiane biosynthesis. As demonstrated here, 1,3-hydride shifts towards guaianes can only be realized for two stereochemically well defined out of numerous possible stereoisomeric skeletons. One example is given by the mechanism of guaia-4(15)-en-11-ol synthase from California poplar, an enzyme that yields guaianes with unusual stereochemical properties. The general results from DFT calculations were experimentally verified through isotopic-labeling experiments with guaia-4(15)-en-11-ol synthase.
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Registered trials
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