Universität zu Köln

Xu, Houchao, Goldfuss, Bernd and Dickschat, Jeroen S. (2021). 1,2-or 1,3-Hydride Shifts: What Controls Guaiane Biosynthesis? Chem.-Eur. J., 27 (38). S. 9758 - 9763. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3765

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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.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Xu, Houchao UNSPECIFIED UNSPECIFIED UNSPECIFIED Goldfuss, Bernd UNSPECIFIED UNSPECIFIED UNSPECIFIED Dickschat, Jeroen S. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-569917
DOI:	10.1002/chem.202101371
Journal or Publication Title:	Chem.-Eur. J.
Volume:	27
Number:	38
Page Range:	S. 9758 - 9763
Date:	2021
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3765
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language SYNTHASE; CYCLASES; DIPHOSPHATE; MECHANISM Multiple languages Chemistry, Multidisciplinary Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/56991