Guenin R, Schneider C H
Immunobiology. 1985 Dec;170(5):412-8. doi: 10.1016/S0171-2985(85)80065-6.
N-[6-(DNCP-amino)hexanoyl]-beta-D-glucopyranosylamine was synthesized and was found to be unable to elicit DNCP-specific passive cutaneous anaphylaxis in the guinea pig. This contrasts with the considerable anaphylactogenicity of N1,N5-bis[2-deoxy-beta-D-glucopyranos-2-yl]-N2-[N3-DNCP-beta -alanyl]glutaminamide which likewise carries a single DNCP haptenic group but a larger carbohydrate moiety, comprised of two glucopyranosylamine groups instead of one. It is concluded that monovalent anaphylactogens, carrying in addition to the haptenic part a carbohydrate auxiliary group, generally require carbohydrate moieties larger than a single monosaccharide unit in order to be effective. Metabolic glucuronic acid conjugation will, therefore, not transform an inactive monovalent hapten into an anaphylactogen when only one glucuronic acid residue is attached.
合成了N-[6-(二硝基氯苯氨基)己酰基]-β-D-吡喃葡萄糖胺，发现其不能在豚鼠中引发二硝基氯苯特异性被动皮肤过敏反应。这与N1,N5-双[2-脱氧-β-D-吡喃葡萄糖-2-基]-N2-[N3-二硝基氯苯-β-丙氨酰]谷氨酰胺的显著过敏原性形成对比，该化合物同样带有单个二硝基氯苯半抗原基团，但碳水化合物部分更大，由两个吡喃葡萄糖胺基团而非一个组成。得出的结论是，除半抗原部分外还带有碳水化合物辅助基团的单价过敏原，通常需要碳水化合物部分大于单个单糖单元才能有效。因此，当仅连接一个葡萄糖醛酸残基时，代谢性葡萄糖醛酸结合不会将无活性的单价半抗原转化为过敏原。
