[Synthesis of conjugates of heptalysine and penicillins (author's transl)].
Heptalysine was synthesized as a non-immunogenic carrier for artificial antigens with penicilloyl-group specificity. The synthesis was carried out by conventional techniques via different routes by condensation of appropriately protected intermediates. Best results were obtained with the use of the benzyloxycarbonyl group for intermediate protection of the alpha-amino-groups and the tert.-butyloxycarbonyl-group together with the tert.-butylester for permanent blockage of the terminal alpha-amino group, the epsilon-amino groups and the terminal carboxyl group. Heptalysine and also lysine were reacted with benzylpenicillin, alpha-aminobenzylpenicillin and tert.-butyloxycarbonyl-alpha aminobenzylpenicillin--to prevent the alpha-amino groups of penicillin from reacting--in aqueous solutions at pH 10.6-11.6 according to Levine and Redmond. The products were isolated after precipitation with acid or dialysation against water by lyophilisation. The penicilloyl group content of the conjugates as estimated from elemental analysis, penamaldate tests and the NMR spectra proved to be rather high: 5-7 residues/mol.
D055598:Chemical Phenomena; D002621:Chemistry; D008722:Methods; D010400:Penicillin G / Q000031:analogs & derivatives; D010406:Penicillins / Q000032:analysis / Q000138:chemical synthesis*; D010455:Peptides / Q000138:chemical synthesis*; D011107:Polylysine / Q000031:analogs & derivatives / Q000032:analysis / Q000138:chemical synthesis*
D010406:Penicillins; D010455:Peptides; D011107:Polylysine; D010400:Penicillin G
Synthese von Konjugaten des Heptalysins mit Penicillinen