Synthese von Konjugaten des Heptalysins mit Penicillinen

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Abstract
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. The 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 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 dialyzation against water by lyophilization. The penicilloyl group content of the conjugates, as estimated from elemental analysis, penamaldate tests and the NMR spectra, was rather high: 5-7 residues/mol.

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