Epoxide hydrolases linalool

Optically pure trans- and czs-linalool oxides, constituents of several plants and fruits, are among the main aroma components of oolong and black tea. These compounds were prepared from 2,3-epoxylinalyl acetate (9) (Scheme 17) [102]. The key step consist of a separation of the diastereomeric mixture of 9 by employing an epoxide hydrolase preparation derived from Rhodococcus sp. NCIMB 11216, yielding the product diol and remaining epoxide in excellent diastereomeric excess (de>98%). Further follow-up chemistry gave both linalool... 

Scheme 17. Synthesis of cis- and frans-linalool oxide using bacterial epoxide hydrolase...

Mischitz, M. and Faber, K. (1996) Chemo-enzymatic s5mthesis of (2R,5S)- and (2R,5R)-5-(1-hydroxy-1-methylethyl)-2-vinyl-tetrahydrofuran ("linalool oxide") preparative application of a highly selective bacterial epoxide hydrolase. Synlett, 978-980. 

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