HYBRID LIPOSOMES COUPLED TO STERIC CONTROL WITH HIGH ENANTIOSELECTIVITY

Citation
K. Goto et al., HYBRID LIPOSOMES COUPLED TO STERIC CONTROL WITH HIGH ENANTIOSELECTIVITY, Journal of organic chemistry, 60(11), 1995, pp. 3342-3346
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
60
Issue
11
Year of publication
1995
Pages
3342 - 3346
Database
ISI
SICI code
0022-3263(1995)60:11<3342:HLCTSC>2.0.ZU;2-D
Abstract
With respect to the hydrolysis of enantiomeric substrates (p-nitrophen yl N-dodecanoyl-D(L)phenylalaninate; C-12-D(L)-Phe-PNP) by the tripept ide catalyst loxycarbonyl)-L-phenylalanyl-L-histidyl-L-leucine; Z-PheH isLeu), a remarkably high enantioselectivity (k(a/obsd)(L)/k(a/obsd)(D ) = 28) along with marked rate-enhancement of the hydrolytic cleavage of C-12-D(L)-Phe-PNP was obtained with specific coaggregates of 32 mol % L-alpha-dipalmitoylphosphatidylcholine (DPPC) and 68 mol % 1,1,3,3- tetramethylbutyl)phenyl]-omega-hydroxypoly (oxy-1,2-ethanediyl)(Triton X-100). Tile enantioselectivity was maximized at the phase transition temperature (T-e) in the 65 mol % DPPC/35 mol % TrixonX-100 and 32 mol % DPPC/68 mol % TritonX-100 coaggregate systems. The hydrophobicity a nd fluidity of the coaggregates can apparently be changed around T-e o n tile basis of isokinetic temperature and fluorescence parameter stud ies.