The stereochemical course of 2-methylisoborneol biosynthesis

被引：3
|
作者：
Gu, Binbin [1 ]
Hou, Anwei [1 ]
Dickschat, Jeroen S. [1 ]
机构：
[1] Univ Bonn, Kekule Inst Organ Chem & Biochem, Gerhard Domagk Str 1, D-53121 Bonn, Germany
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 18卷
关键词：
biosynthesis; enantioselective synthesis; enzyme mechanisms; gas chromatography; terpenoids; OFF-FLAVOR; STREPTOMYCES-COELICOLOR; VOLATILE METABOLITES; ODOR; METHYLISOBORNEOL; COMPONENTS; SECONDARY; ALCOHOLS; GEOSMIN;
D O I：
10.3762/bjoc.18.82
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：818 / 824
页数：7
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