ISSN:
0894-3230
Keywords:
Organic Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
The rate of intramolecular degradation of cephaclor, involving the attack of the amino group at C-17 (N-18) on the β-lactam carbonyl, was increased up to 50-fold by neutral (polyoxyethylene-23 lauryl ether; Brij) and zwitterionic [3-(N-dodecyl-N, N-dimethylammonium) propane 1-sulphonate; (SDP)] micelles. The rate of OH- attack on cephaclor was increased 2-3-fold by Brij and SDP micelles. In the absence of micelles the rate of intramolecular degradation of cephaclor increased by up to 2-fold by addition of organic solvents. Distance calculations, based on the crystal structure of the antibiotic, showed that the intramolecular degration can only proceed in a conformation involving a cis-amide bond (N-14 - C-15). Micellar catalysis of the intramolecular degradation process was proposed to be due to the stabilization of the reactive conformation.
Additional Material:
6 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/poc.610040105
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