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由(R)-柠檬烯通过化学酶法合成手性纯的(R)-和(S)-卡拉哈那烯醇。

Chemoenzymatic synthesis of homochiral (R)- and (S)-karahanaenol from (R)-limonene.

作者信息

Roy A

机构信息

Plantation Products and Flavor Technology Discipline, Central Food Technological Research Institute, Mysore 570 013, India.

出版信息

J Agric Food Chem. 1999 Dec;47(12):5209-10. doi: 10.1021/jf990531a.

DOI:10.1021/jf990531a
PMID:10606597
Abstract

Terpinolene oxide, a monoterpene belonging to the p-menthane group, is easily derived from naturally abundant (R)-limonene. It was isomerized with montmorillonite clay catalyst to karahanaenone (2,2, 5-trimethylcyclohept-4-en-1-one) by ring enlargement. The enantiomers of the corresponding alcohol, karahanaenol (2,2, 5-trimethylcyclohept-4-en-1- ol), known for their individual organoleptic properties, were resolved through Pseudomonas cepacia lipase mediated enantiospecific alcoholysis of its acetate derivative.

摘要

氧化萜品烯是一种属于对薄荷烷类的单萜,很容易从天然丰富的(R)-柠檬烯衍生而来。它在蒙脱石粘土催化剂作用下通过扩环异构化为卡拉花烯酮(2,2,5-三甲基环庚-4-烯-1-酮)。相应的醇卡拉花烯醇(2,2,5-三甲基环庚-4-烯-1-醇)的对映体因其各自的感官特性而闻名,通过洋葱假单胞菌脂肪酶介导的其乙酸酯衍生物的对映体特异性醇解得以拆分。

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