Microbial synthesis of chiral intermediates for β-3-receptor agonists
摘要：
Chiral intermediates were prepared by biocatalytic processes for the chemical synthesis of β-3-receptor agonists. These include: (i) the microbial reduction of 4-benzyloxy-3-methanesulfonylamino-2′-bromoacetophenone 1 to the corresponding ( R )-alcohol 2 by Spingomonas paucimobilis SC 16113. In the biotransformation process, a reaction yield of >85% and an optical purity of 99.5% were obtained for the desired ( R )-alcohol 2 ; (ii) the enzymatic resolution of racemic α-methyl phenylalanine amide, 3 , and α-methyl-4-hydroxy-phenylalanine amide, 5 , by amidase from Mycobacterium neoaurum ATCC 25795 to prepare the corresponding ( S )-amino acids 4 and 6 . Reaction yields of 49.9 and 49 M% (theoretical maximum yield 50 M%) and optical purities of 99 and 94% were obtained for the desired ( S )-amino acids 4 and 6 , respectively; (iii) the asymmetric hydrolysis of methyl-(4-methoxyphenyl)-propanedioic acid, ethyl diester, 7 , to the corresponding ( S )-monoester 8 by pig liver esterase. A reaction yield of 96 M% and an optical purity of 96% were obtained for ( S )-monoester 8 when reactions were carried out in a biphasic system containing 10% ethanol at 10°C.
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关键词：
Asymmetric hydrolysis biocatalysis chiral intermediates pig liver esterase β-3-receptor agonist resolution using amidase stereoselective reduction
DOI：
10.1007/s11746-998-0081-0
被引量：
年份：
1998
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