A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus

Beilstein Journal of Organic Chemistry

Laura zur Horst¹  Jan Rinkel¹  Jeroen S. Dickschat¹  Patrick Rabe¹ 

[1] Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany;

关键词: biosynthesis;    enzyme mechanisms;    isotopic labelling;    stereochemistry;    terpenes;   

DOI  :  10.3762/bjoc.12.225

来源: DOAJ

【 摘 要 】

The stereochemical course of the cyclisation reaction catalysed by the bacterial 1,8-cineol synthase from Streptomyces clavuligerus was investigated using stereospecifically deuterated substrates. In contrast to the well investigated plant enzyme from Salvia officinalis, the reaction proceeds via (S)-linalyl diphosphate and the (S)-terpinyl cation, while the final cyclisation reaction is in both cases a syn addition, as could be shown by incubation of (2-13C)geranyl diphosphate in deuterium oxide.

【 授权许可】

Unknown