Schnabel E
Hoppe Seylers Z Physiol Chem. 1976 Dec;357(10):1365-77.
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.
庚赖氨酸被合成为一种具有青霉素酰基特异性的人工抗原的非免疫原性载体。合成是通过常规技术，经由不同路线，通过适当保护的中间体的缩合来进行的。使用苄氧羰基对α-氨基进行中间体保护，同时使用叔丁氧羰基和叔丁酯对末端α-氨基、ε-氨基和末端羧基进行永久性封闭，可获得最佳结果。根据莱文和雷德蒙德的方法，庚赖氨酸以及赖氨酸在pH 10.6 - 11.6的水溶液中与苄青霉素、α-氨基苄青霉素和叔丁氧羰基-α-氨基苄青霉素反应（以防止青霉素的α-氨基发生反应）。产物通过酸沉淀或对水透析后冻干进行分离。通过元素分析、青霉素马来酸酯试验和核磁共振光谱估计，缀合物中的青霉素酰基含量相当高：5 - 7个残基/摩尔。
