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Enantioselective synthesis of ( S )‐2‐amino‐4‐phenylbutanoic acid by the hydantoinase method
Author(s) -
Lo HsuehHsia,
Kao ChaoHung,
Lee DongSheng,
Yang TengKuei,
Hsu WenHwei
Publication year - 2003
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10281
Subject(s) - chemistry , enantioselective synthesis , imidazolidine , substrate (aquarium) , biocatalysis , amino acid , high performance liquid chromatography , stereochemistry , catalysis , chromatography , organic chemistry , biochemistry , reaction mechanism , oceanography , geology
Biosynthesis of ( S )‐(+)‐2‐amino‐4‐phenylbutanoic acid ( 1 ) was performed by nonenantioselective hydantoinase and L ‐ N ‐carbamoylase using racemic 5‐[2‐phenylethyl]‐imidazolidine‐2,4‐dione ( rac ‐ 2 ) as a substrate. The compounds involved in this biocatalysis process could be simultaneously resolved by high‐performance liquid chromatography using Chirobiotic T column with a mobile phase of EtOH/H 2 O = 10/90 at pH 4.2–4.5. To our knowledge, this is the first report of the successful production of 1 by the combination of recombinant hydantoinase and L ‐ N ‐carbamoylase. Chirality 15:699–702, 2003. © 2003 Wiley‐Liss, Inc.