[Hydrolysis of the amidine analogs of penicillins].
The products of the hydrolytic degradation of 6-beta-(hexahydro-IH-azepenyl-1)methylenamino) penicillanic acid, 6-beta-(N,N-dimethylformamidino-N1)-penicillanic acid and 6-beta-(morpholinyl-1)methylenamino penicillanic acid were identified with the method of thin-layer chromatography and paper electrophoresis in neutral, acid and alkaline solutions and in the presence of penicillinase. The data of the study showed that acid hydrolysis of the amidine analogues of penicillins resulted in cleavage of the beta-lactame cycle and formation of the respective penicillanic acids. In the alkaline medium the secondary amine (hexamethylenimine, dimethylamine, morpholine) was cleaved from the antibiotic side chain and the resulting N-formyl-6-aminopenicillanic acid was further cleaved up to peniciec acid. The beta-lactame cycle of the antibiotics was cleaved under the effect of penicillinase and the resulting penicilloinic acids degraded into peniciec acid, N-formylpeniciec acid and secondary amines. In the nutral solution the antibiotics were transformed into N-formyl-6-aminopenicillanic acid and penicilloinic acids at the first stage of the hydrolysis followed by their further degradation with formation of N-formylpeniciec acid, peniciec acid and secondary amines.
D000578:Amidines / Q000032:analysis / Q000378:metabolism*; D001407:Bacillus / Q000201:enzymology; D002855:Chromatography, Thin Layer; D004590:Electrophoresis, Paper; D006868:Hydrolysis; D066298:In Vitro Techniques; D010405:Penicillinase / Q000378:metabolism; D010406:Penicillins / Q000032:analysis / Q000378:metabolism*; D013055:Spectrophotometry, Infrared
D000578:Amidines; D010406:Penicillins; D010405:Penicillinase
Gidroliz amidinovykh analogov penitsillinov.