Stereoselective Enzymatic Synthesis of cis-Pellitorine, a Taste Active Alkamide Naturally Occurring in Tarragon

✍ Scribed by Jakob P. Ley; Jens-Michael Hilmer; Berthold Weber; Gerhard Krammer; Ian L. Gatfield; Heinz-Jürgen Bertram

• Book ID: 102176712
• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 120 KB
• Volume: 2004
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200400403

✦ Synopsis

Abstract

The alkamide cis‐pellitorine [(2__E__,4__Z__)‐N‐isobutyldeca‐2,4‐dienamide] that occurs naturally in tarragon was prepared in yields up to 80% by lipase‐catalyzed conversion of ethyl 2__E__,4__Z__‐decadienoate, the so‐called pear ester, and isobutylamine both with and without the use of cosolvents. Of 13 different commercial enzyme preparations tested (lipases, proteases, esterases), only the lipase type B from Candida antarctica has a suitable activity. The reaction of the different geometric isomers of ethyl 2,4‐decadienoate to the appropriate pellitorines shows a remarkable selectivity: the 2__E__,4__Z__ ester is converted between 1.4 and 3.9 times faster than the 2__E__,4__E__ isomer, and the relative yield of cis‐pellitorine compared with trans‐pellitorine is 5.7 to 16.3 times higher. In contrast to the better known trans‐pellitorine, which at 10 ppm is only slightly tingling and numbing, cis‐pellitorine shows very interesting pungent and warming sensations after tasting trials already in low concentrations of 10 ppm. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)