ISSN:
0025-116X
Keywords:
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
The enantioselective hydrolysis of dipeptide-type amino acid esters (Z-(L)-Ala-(L or D)-Ala-PNP (5a), Z-(L)-Ala-(L or D)-Leu-PNP (5b), and Z-(L)-Ala-(L or D)-Phe-PNP (5c)) by di- or tri-peptide nucleophiles (Z-(L)-Leu-(L)-His (2a), Z-(L)-Phe-(L)-His (2b), and Z-(L)-Leu-(L)-His (3)) in the bilayer vesicular aggregates of didodecyldimethylammonium bromide (6) resulted in the enantiomer rate ratio of LL/LD = 1, 1 to 18, the value of which was considerably higher than that (L/D = 1,0 to 4,6) in the hydrolysis of Z-(L or D)-Ala-PNP (4a), Z-(L or D)-Leu-PNP (4b), and Z-(L or D)-Phe-PNP (4c) by the identical vesicular system and that (L/D = 0,7 to 3,1) in the hydrolysis of the dipeptide substrates 5a - c by Z-(L)-His (1) and 6. The high enantioselectivity (LL/LD = 18) in the hydrolysis of 5c by the system of 2a and 6 was enhanced to be LL/LD = 36 by lowering the temperature from 25 to 10°C.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/macp.1984.021850505
