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Lipase-Catalyzed Enantiomer Separation of 3-Hydroxy-4-(tosyloxy)butanenitrile: Synthesis of (R)-GABOB (=(3R)-4-Amino-3-hydroxybutanoic Acid) and (R)-Carnitine Hydrochloride (=(2R)-3-Carboxy-2-hydroxy-N,N,N-trimethylpropan-1-aminium Chloride)

✍ Scribed by Ahmed Kamal; G. B. Ramesh Khanna; Tadiparthi Krishnaji

Publisher: John Wiley and Sons
Year: 2007
Tongue: German
Weight: 88 KB
Volume: 90
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200790180

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✦ Synopsis

Abstract

Enzymatic resolution of racemic 3‐hydroxy‐4‐(tosyloxy)butanenitrile ((±)‐5) by using various lipases in different solvents were studied. The obtained optically pure (3__R__)‐3‐(acetyloxy)‐4‐(tosyloxy)butanenitrile ((R)‐6), upon treatment with aqueous ammonia followed by conc. HCl solution, provided (R)‐GABOB (=(3__R__)‐4‐amino‐3‐hydroxybutanoic acid; (R)‐1). Similarly, reaction of (R)‐6 with aqueous trimethylamine solution followed by conc. HCl solution provided (R)‐carnitine hydrochloride (=(2__R__)‐3‐carboxy‐2‐hydroxy‐N,N,N‐trimethylpropan‐1‐aminium chloride; (R)‐2⋅HCl) in an expeditious manner.

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