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Enzymatic resolution of ( S )‐(+)‐Naproxen in a trapped aqueous–organic solvent biphase continuous reactor
Author(s) -
Xin JiaYing,
Li ShuBen,
Xu Yi,
Wang LaiLai
Publication year - 2000
Publication title -
biotechnology and bioengineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.136
H-Index - 189
eISSN - 1097-0290
pISSN - 0006-3592
DOI - 10.1002/(sici)1097-0290(20000405)68:1<78::aid-bit9>3.0.co;2-i
Subject(s) - continuous stirred tank reactor , chemistry , aqueous solution , hydrolysis , product inhibition , membrane reactor , aqueous two phase system , substrate (aquarium) , lipase , chromatography , naproxen , immobilized enzyme , organic chemistry , catalysis , enzyme , medicine , oceanography , non competitive inhibition , alternative medicine , pathology , geology
A trapped aqueous–organic biphase system for the continuous production of ( S )‐(+)‐2‐(6‐methoxy‐2‐naphthyl) propionic acid (Naproxen) has been developed. The process consists of a stereoselective hydrolysis of the racemic Naproxen methyl ester by Candida rugosa lipase in a trapped aqueous–organic biphase system. The reaction has been carried out in a laboratory‐scale continuous‐flow stirred tank reactor (CSTR). The staring material has been supplied in and remaining substrate recovered by organic phase. YWG‐C 6 H 5 , a poorly polar synthetic support, has been employed to immobilize the lipase and to restrict the aqueous phase. Lipase immobilized on YWG‐C 6 H 5 containing aqueous phase has been added into the CSTR to catalyze the hydrolysis. A dialysis membrane tube containing a continuous flow closed‐loop buffer has been applied in the CSTR for the extraction of product and recruiting of the aqueous part consumed. Various reaction conditions have been studied. The activity of immobilized enzyme was effected by the polarity of support, the substrate concentration, logP value of organic phase and the product inhibition. At steady‐state operating conditions, an initial conversion of 35% has been obtained. The CSTR was allowed to operate continuously for 60 days at 30°C with a 30% loss of activity. The hydrolysis reaction yielded ( S )‐(+)‐Naproxen with >90% enantiomeric excess and overall conversion of 30%. © 2000 John Wiley & Sons, Inc. Biotechnol Bioeng 68:78‐83, 2000.