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Lipase‐Catalyzed Enantiomer Separation of 3‐Hydroxy‐4‐(tosyloxy)butanenitrile: Synthesis of ( R )‐GABOB (=(3 R )‐4‐Amino‐3‐hydroxybutanoic Acid) and ( R )‐Carnitine Hydrochloride (=(2 R )‐3‐Carboxy‐2‐hydroxy‐ N , N , N ‐trimethylpropan‐1‐aminium Chloride)
Author(s) -
Kamal Ahmed,
Khanna G. B. Ramesh,
Krishnaji Tadiparthi
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790180
Subject(s) - chemistry , hydrochloride , aqueous solution , enantiomer , ammonia , chloride , catalysis , lipase , medicinal chemistry , trimethylamine , organic chemistry , stereochemistry , enzyme
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.