The stereochemical course of 2-methylisoborneol biosynthesis

Name: The stereochemical course of 2-methylisoborneol biosynthesis
Keywords: enzyme mechanisms, QD241-441, Letter, terpenoids, gas chromatography, Science, Q, Organic chemistry, enantioselective synthesis, biosynthesis

Binbin Gu; Anwei Hou; Jeroen S Dickschat

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Beilstein Journal of Organic Chemistry

Article . 2022 . Peer-reviewed

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Beilstein Journal of Organic Chemistry

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Other literature type . 2022

License: http://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (http://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0 (http://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.

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Beilstein Journal of Organic Chemistry

Article . 2022

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The stereochemical course of 2-methylisoborneol biosynthesis

descriptionPublicationkeyboard_double_arrow_right Article , Other literature type 08 Jul 2022 English Publisher:Beilstein InstitutJournal:Beilstein Journal of Organic Chemistry, volume 18, pages 818-824 (eissn: 1860-5397,

Copyright policy )Funded by:DFG | unidentified

Authors: Binbin Gu; Anwei Hou; Jeroen S Dickschat;

doi: 10.3762/bjoc.18.82

pmid: 35875708

pmc: PMC9273983

The stereochemical course of 2-methylisoborneol biosynthesis

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Abstract

Both enantiomers of 2-methyllinalyl diphosphate (2-Me-LPP) were synthesized enantioselectively using Sharpless epoxidation as a key step and purification of enantiomerically enriched intermediates through HPLC separation on a chiral stationary phase. Their enzymatic conversion with 2-methylisoborneol synthase (2MIBS) demonstrates that (R)-2-Me-LPP is the on-pathway intermediate, while a minor formation of 2-methylisoborneol from (S)-2-Me-LPP may be explained by isomerization to 2-Me-GPP and then to (R)-2-Me-LPP.

Related Organizations

University of Bonn
Germany
University of Bonn
Germany

Keywords

enzyme mechanisms, QD241-441, Letter, terpenoids, gas chromatography, Science, Q, Organic chemistry, enantioselective synthesis, biosynthesis

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