2-甲基异冰片醇生物合成的立体化学过程。
The stereochemical course of 2-methylisoborneol biosynthesis.
作者信息
Gu Binbin, Hou Anwei, Dickschat Jeroen S
机构信息
Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany.
出版信息
Beilstein J Org Chem. 2022 Jul 8;18:818-824. doi: 10.3762/bjoc.18.82. eCollection 2022.
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 ()-2-Me-LPP is the on-pathway intermediate, while a minor formation of 2-methylisoborneol from ()-2-Me-LPP may be explained by isomerization to 2-Me-GPP and then to ()-2-Me-LPP.
以夏普莱斯环氧化反应作为关键步骤，通过在手性固定相上进行高效液相色谱分离对映体富集的中间体，对2-甲基里哪醇二磷酸酯（2-Me-LPP）的两种对映体进行了对映选择性合成。它们与2-甲基异冰片合酶（2MIBS）的酶促转化表明，（+）-2-Me-LPP是途径中的中间体，而由（-）-2-Me-LPP少量生成2-甲基异冰片可通过异构化为2-Me-GPP然后再异构化为（+）-2-Me-LPP来解释。
Zotero 插件