Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Notes
Steric-Control for the Enantioselective Hydrolysis of Amino Acid Esters in Hybrid Membrane Systems
Osamu TanoueHideaki IchiharaKoichi GotoYoko MatsumotoRyuichi Ueoka
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2003 Volume 51 Issue 2 Pages 224-226

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Abstract
The enantioselective hydrolysis of the amino acid esters, p-nitrophenyl-N-dodecanoyl-D(L)-phenylalaninates (C12-D(L)-Phe-PNP) catalyzed by active tripeptide, N-(benzyloxycarbonyl)-L-phenylalanyl-L-histidyl-L-leucine (Z-PheHisLeu) in the presence of coaggregates (hybrid membranes) composed of native phospholipid, L-α-dimyristoylphosphatidylcholine (DMPC) and nonionic surfactant, polyoxyethylene (8) lauryl ether (C12(EO)8) was easily controlled by regulating the reaction temperature and changing the composition of coaggregates. Furthermore, excellent correlations were observed between the enantioselectivity in the hydrolysis of C12-D(L)-Phe-PNP catalyzed by Z-PheHisLeu in the presence of coaggregates and physical properties of hybrid membranes. It is assumed that catalytic activities of tripeptide catalyst in hybrid membranes should be regulated by changing the microenvironments of reaction fields.
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© 2003 The Pharmaceutical Society of Japan
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