Synthesis of (S)-alpha-amino oleic acid
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Updated: Oct 2, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Victoria Magrioti1, Violetta Constantinou-Kokotou
1Chemical Laboratories, Agricultural University of Athens, Greece.
Abstract:
An efficient synthesis of (S)-alpha-amino oleic acid was developed. The fully protected FA derivative was obtained in four steps starting from methyl (2S)-2-[bis(tert-butoxycarbonyl)amino]-5-oxopentanoate. These steps are (i) olefination of the starting aldehyde with the appropriate phosphonate anion, (ii) hydrogenation of the double bonds, (iii) controlled reduction of omega-ethyl ester to an aldehyde in the presence of alpha-methyl ester, and (iv) a Wittig reaction of the latter aldehyde with the suitable ylide. Free alpha-amino oleic acid was prepared after deprotection of the amino group followed by saponification in a total yield of 24%. N-tert-Butoxycarbonyl-protected amino oleic acid and the corresponding amino alcohol were prepared in high yield. The structures of the products have been established by various spectroscopic techniques.
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