The chemoenzymatic synthesis of(S)-13-hydroxyoctadeca-(9Z, 11E)-dienoic acid using the hydroxynitrile lyase from Hevea brasiliensis

✍ Scribed by Dean V. Johnson; Herfried Griengl

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 566 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)01023-x

✦ Synopsis

Absrruct: (S')-13-Hydroxyoctadeca-(9Z, I I,?)-dienoic acid (1) was synthesized in nine steps starting from (Q-2-octenal (2). The (S)-hydroxynitrile lyase cloned from Hewa brasiliensis, that has been overexpressed in Pi&a pastoris, was used to interconvert 2 into (S)-cyanohydrin 3, The subsequent butyrate 6 was rearranged using the palladium-his-(acetonitrile)-dichloride to give the unsaturated nitrile 7 which was fully elaborated to the hydroxy acid 1 in an overall 11% yield and with 99% e.e.