Moroder L, Gobbo M, Becker G, Wünsch E
Max-Planck-Institut für Biochemie, Abteilung Peptidchemie, Martinsried München.
Biol Chem Hoppe Seyler. 1989 Apr;370(4):365-75. doi: 10.1515/bchm3.1989.370.1.365.
N-Acetylmuramyl-dipeptide and tripeptide derivatives containing at the C-terminus a masked thiol function, i.e. the S-tert-butylthiocysteamine residue, were synthesized via direct condensation of N-acetylmuramic acid with the peptide moiety using the dicyclohexylcarbodiimide/N-hydroxysuccinimide procedure. Reduction with tributylphosphine in aqueous organic media generates the free thiol function for a selective conjugation of these immunomodulants with target molecules via unsymmetrical disulfide bridging with a second thiol group by the sulfenohydrazide procedure or via thio-ether linkage by the addition to maleimido--or aziridine-derivatives.
通过使用二环己基碳二亚胺/N-羟基琥珀酰亚胺方法，将N-乙酰胞壁酸与肽部分直接缩合，合成了在C端含有掩蔽硫醇功能（即S-叔丁基硫代半胱胺残基）的N-乙酰胞壁酰二肽和三肽衍生物。在水性有机介质中用三丁基膦还原可产生游离硫醇功能，以便通过亚磺酰肼法与第二个硫醇基团形成不对称二硫键桥联，或通过加成到马来酰亚胺或氮丙啶衍生物上形成硫醚键，将这些免疫调节剂与靶分子进行选择性缀合。
