Journal of Organic Chemistry p. 3342 - 3346 (1995)
Update date:2022-09-26
Topics:
Goto, Koichi
Matsumoto, Yoko
Ueoka, Ryuichi
With respect to the hydrolysis of enantiomeric substrates (p-nitrophenyl N-dodecanoyl-D(L)-phenylalaninate; C12-D(L)-Phe-PNP) by the tripeptide catalyst (N-(benzyloxycarbonyl)-L-phenylalanyl-L-histidyl-L-leucine; Z-PheHisLeu), a remarkably high enantioselectivity (kLa/obsd/kDa/obsd = 28) along with marked rate-enhancement of the hydrolytic cleavage of C12-D(L)-Phe-PNP was obtained with specific coaggregates of 32 mol percent L-α-dipalmitoylphosphatidylcholine (DPPC) and 68 mol percent α-<4-(1,1,3,3-tetramethylbutyl)phenyl>-ω-hydroxypoly(oxy-1,2-ethanediyl) (TritonX-100).The enantioselectivity was maximized at the phase transition temperature (Tc) in the 65 mol percent DPPC/35 mol percent TritonX-100 and 32 mol percent DPPC/68 mol percent TritonX-100 coaggregate systems.The hydrophobicity and fluidity of the coaggregates can apparently be changed around Tc on the basis of isokinetic temperature and fluorescence parameter studies.
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