Fujiwara T, Aspinall G O, Hunter S W, Brennan P J
Carbohydr Res. 1987 Jun 1;163(1):41-52. doi: 10.1016/0008-6215(87)80163-5.
O-(3,6-Di-O-methyl-beta-D-glucopyranosyl)-(1----4)-O-(2,3-di-O-methyl- alpha-L-rhamnopyranosyl)-(1----2)-3-O-methyl-L-rhamnopyranose, the haptenic trisaccharide of the Mycobacterium leprae-specific phenolic glycolipid I (PGL-I) antigen, and related trisaccharides, were synthesized by allylation of O-2 of benzyl 4-O-benzyl-alpha-L-rhamnopyranoside using phase-transfer catalysis, methylation of the product, deallylation, and coupling to O-(2,4-di-O-acetyl-3,6-di-O-methyl-beta-D-glucopyranosyl)-(1----4)-2,3- di-O-methyl-L-rhamnopyranosyl bromide or related disaccharides. Anomeric mixtures of the trisaccharide derivatives were separated by preparative t.l.c., deacetylated, and hydrogenolyzed, to give the pure trisaccharides. It had already been demonstrated that only those trisaccharides containing an intact, terminal 3,6-di-O-methyl-beta-D-glucopyranosyl unit are effective in inhibiting the specific binding between PGL-I and anti-PGL-I immunoglobulin M antibodies in human lepromatous leprosy sera.
O-(3,6-二-O-甲基-β-D-吡喃葡萄糖基)-(1→4)-O-(2,3-二-O-甲基-α-L-吡喃鼠李糖基)-(1→2)-3-O-甲基-L-吡喃鼠李糖，即麻风分枝杆菌特异性酚糖脂I（PGL-I）抗原的半抗原三糖，以及相关三糖，通过使用相转移催化对苄基4-O-苄基-α-L-吡喃鼠李糖苷的O-2进行烯丙基化、产物的甲基化、脱烯丙基化，以及与O-(2,4-二-O-乙酰基-3,6-二-O-甲基-β-D-吡喃葡萄糖基)-(1→4)-2,3-二-O-甲基-L-吡喃鼠李糖基溴或相关二糖偶联来合成。三糖衍生物的异头物混合物通过制备薄层层析分离、脱乙酰化并进行氢解，以得到纯三糖。已经证明，只有那些含有完整末端3,6-二-O-甲基-β-D-吡喃葡萄糖基单元的三糖能够有效抑制人瘤型麻风血清中PGL-I与抗PGL-I免疫球蛋白M抗体之间的特异性结合。
