Universität zu Köln

Xu, Houchao ORCID: 0000-0002-4480-2035, Goldfuss, Bernd, Schnakenburg, Gregor and Dickschat, Jeroen S. (2022). The enzyme mechanism of patchoulol synthase. Beilstein J. Org. Chem., 18. S. 13 - 25. FRANKFURT AM MAIN: BEILSTEIN-INSTITUT. ISSN 1860-5397

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Abstract

Different mechanisms for the cyclisation of farnesyl pyrophosphate to patchoulol by the patchoulol synthase are discussed in the literature. They are based on isotopic labelling experiments, but the results from these experiments are contradictory. The present work reports on a reinvestigation of patchoulol biosynthesis by isotopic labelling experiments and computational chemistry. The results are in favour of a pathway through the neutral intermediates germacrene A and alpha-bulnesene that are both reactivated by protonation for further cyclisation steps, while previously discussed intra- and intermolecular hydrogen transfers are not supported. Furthermore, the isolation of the new natural product (2S,3S,7S,10R)-guaia-1,11-dien-10-ol from patchouli oil is reported.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Xu, Houchao UNSPECIFIED orcid.org/0000-0002-4480-2035 UNSPECIFIED Goldfuss, Bernd UNSPECIFIED UNSPECIFIED UNSPECIFIED Schnakenburg, Gregor UNSPECIFIED UNSPECIFIED UNSPECIFIED Dickschat, Jeroen S. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-667463
DOI:	10.3762/bjoc.18.2
Journal or Publication Title:	Beilstein J. Org. Chem.
Volume:	18
Page Range:	S. 13 - 25
Date:	2022
Publisher:	BEILSTEIN-INSTITUT
Place of Publication:	FRANKFURT AM MAIN
ISSN:	1860-5397
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language POGOSTEMON-CABLIN; SESQUITERPENES; BIOSYNTHESIS; ALCOHOL; CYCLASES Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/66746