Alkan S S, Bush M E, Nitecki D E, Goodman J W
J Exp Med. 1972 Aug 1;136(2):387-91. doi: 10.1084/jem.136.2.387.
The low molecular weight compound L-tyrosine-azobenzenearsonate (RAT) induces a cellular immune response in guinea pigs. The contribution of the side chain of tyrosine to the immunogenicity of RAT and the structural requirements at that position for immunogenicity were assessed by synthesizing a series of analogs of RAT containing modifications in the side chain of tyrosine and employing them as immunogens. Removal of either the carboxyl or amino group did not markedly affect immunogenicity, measured by the induction of delayed cutaneous sensitivity, whereas deletion of both completely abolished it. However, a charged group was not required since side chains containing a polar hydroxyl group could substitute for chains bearing an amino or carboxyl group. The size of the side chain exerted a pronounced influence; the charged or polar substituent had to be extended from the phenolic ring by at least two carbon atoms in order to confer immunogenicity.
低分子量化合物L-酪氨酸-偶氮苯胂酸盐（RAT）可在豚鼠中诱导细胞免疫反应。通过合成一系列酪氨酸侧链有修饰的RAT类似物并将其用作免疫原，评估了酪氨酸侧链对RAT免疫原性的贡献以及该位置产生免疫原性的结构要求。通过迟发型皮肤敏感性诱导来衡量，去除羧基或氨基均未显著影响免疫原性，而两者都缺失则完全消除了免疫原性。然而，并不需要带电荷基团，因为含有极性羟基的侧链可以替代带有氨基或羧基的链。侧链的大小产生了显著影响；带电荷或极性取代基必须从酚环延伸至少两个碳原子才能赋予免疫原性。
