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)

被引：12
|
作者：
Kamal, Ahmed [1 ]
Khanna, G. B. Ramesh [1 ]
Krishnaji, Tadiparthi [1 ]
机构：
[1] Indian Inst Chem Technol, Div Organ Chem, Biotransformat Lab, Hyderabad 500007, Andhra Pradesh, India
来源：
HELVETICA CHIMICA ACTA | 2007年 / 90卷 / 09期
关键词：
D O I：
10.1002/hlca.200790180
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Enzymatic resolution of racemic 3-hydroxy-4-(tosyloxy)butanenitrile ((+/-)-5) by using various lipases in different solvents were studied. The obtained optically pure (3R)-3-(acetyloxy)-4-(tosyloxy)butanenitrile ((R)-6), upon treatment with aqueous ammonia followed by cone. HCl solution, provided (R)-GABOB (=(3R)-4-amino-3-hydroxybutanoic acid; (R)4). Similarly, reaction of (R)-6 with aqueous trimethylamine solution followed by conc. HCl solution provided (R)-carnitine hydrochloride (=(2R)-3-carboxy-2-hydroxy-N,N,N-trimethylpropan-1-aminium chloride; (R)-2 HCl) in an expeditious manner.
引用
收藏
页码：1723 / 1730
页数：8
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