Lemieux R U, LePendu J, Hindsgaul O
Jpn J Antibiot. 1979 Dec;32 Suppl:S21-31.
The coincidence of the presence of ABH active substances in the saliva of persons with those individuals who possess either LEWIS-d or LEWIS-b antigens on epithelial cells of their stomach tissues is examined in terms of the three-dimensional conformations of the oligosaccharide structures which form the ABH and LEWIS antigenic determinants. The H activity in saliva is normally established by examining the inhibition of the agglutination of human H red cells, which possess H (Type 2) determints at their surface, by the lectin Ulex europaeus. As was to be expected, the LEWIS-d (H-Type 1) (alpha LFuc (1 leads to 2) beta DGal (1 leads to 3) beta DGlcNAcOR, R = (CH2)8COOCH3) and LEWIS-b (alpha LFuc (1 leads to 2) beta DGal (1 leads to 3) [alpha LFuc (1 leads to 4)] beta DGlcNAcOR) determinants, obtained by chemical synthesis, do not bind Ulex. However, these structures in the de-N-acetylated form proved to do so as evidenced by their ability to inhibit the agglutination. These results together with results obtained in inhibition studies involving chemically modified H (Type 1) and H (Type 2) structures are rationalized in terms of conformational analysis and raise the possibility that the LEWIS-b and d antigens in saliva are present with the determinants in the amine form. The circumstantial evidence obtained in support of this possibility is, as yet, inconclusive. The main thrust of the paper is to indicate how modern conformational analysis may play an important role in the improvement of knowledge in carbohydrate-receptor site interaction.
根据构成ABH和LEWIS抗原决定簇的寡糖结构的三维构象,研究了胃组织上皮细胞上具有LEWIS-d或LEWIS-b抗原的个体唾液中ABH活性物质的存在情况。唾液中的H活性通常通过检测荆豆凝集素对人H红细胞凝集的抑制作用来确定,人H红细胞表面具有H(2型)决定簇。正如预期的那样,通过化学合成获得的LEWIS-d(H-1型)(α-L-岩藻糖(1→2)β-D-半乳糖(1→3)β-D-葡萄糖胺OR,R =(CH2)8COOCH3)和LEWIS-b(α-L-岩藻糖(1→2)β-D-半乳糖(1→3)[α-L-岩藻糖(1→4)]β-D-葡萄糖胺OR)决定簇不与荆豆结合。然而,去N-乙酰化形式的这些结构被证明可以结合,这可以通过它们抑制凝集的能力来证明。这些结果以及在涉及化学修饰的H(1型)和H(2型)结构的抑制研究中获得的结果,通过构象分析得到了合理的解释,并提出了唾液中的LEWIS-b和d抗原可能以胺形式存在决定簇的可能性。支持这种可能性的间接证据目前尚无定论。本文的主要目的是指出现代构象分析如何在改善碳水化合物-受体位点相互作用的知识方面发挥重要作用。