Lee R T, Lee Y C
Department of Biology, McCollum-Pratt Institute, Johns Hopkins University, Baltimore, Maryland 21218.
Carbohydr Res. 1994 Jan 3;251:69-79. doi: 10.1016/0008-6215(94)84276-0.
Syntheses of galactose derivatives that are useful in probing the binding specificity of galactose-specific lectins are reported. These include allyl 3-deoxy- and 4-deoxy-beta-D-xylo-hexopyranoside and several disaccharide glycosides having Gal(1-->2) and Gal(1-->3) linkages. The beta-linked Gal disaccharide isomers were produced using 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide as glycosyl donor and the 4,6-O-benzylidene derivatives of allyl beta-D-galactopyranoside, alpha-D-glucopyranoside, alpha-D-mannopyranoside, and 2-acetamido-2-deoxy-alpha-D-galactopyranoside as acceptors. Only the Gal(1-->3)-linked disaccharide was obtained when the benzylidene derivatives of the mannopyranoside and 2-acetamido-2-deoxygalactopyranoside were used. Attempts at the preparation of Gal(alpha, 1-->2)Gal and Gal(alpha, 1-->3)Gal disaccharide glycosides were made using the same strategy, but employing the 1-trichloro-acetimidate or 1-N-methylacetimidate of 2,3,4,6-tetra-O-benzyl-D-galactopyranose as the glycosyl donor. The latter imidate produced a mixture of Gal(alpha, 1-->2)Gal and Gal(alpha, 1-->3)Gal derivatives as major products, but the former gave the Gal(beta, 1-->2)Gal isomer as the major product.
报道了可用于探究半乳糖特异性凝集素结合特异性的半乳糖衍生物的合成。这些衍生物包括烯丙基3 - 脱氧 - 和4 - 脱氧 - β - D - 吡喃木糖己糖苷以及几种具有Gal(1→2)和Gal(1→3)连接的二糖糖苷。β - 连接的半乳糖二糖异构体是使用2,3,4,6 - 四 - O - 乙酰基 - α - D - 吡喃半乳糖基溴作为糖基供体，以及烯丙基β - D - 吡喃半乳糖苷、α - D - 吡喃葡萄糖苷、α - D - 吡喃甘露糖苷和2 - 乙酰氨基 - 2 - 脱氧 - α - D - 吡喃半乳糖苷的4,6 - O - 亚苄基衍生物作为受体来制备的。当使用甘露糖苷和2 - 乙酰氨基 - 2 - 脱氧半乳糖苷的亚苄基衍生物时，仅得到了Gal(1→3)连接的二糖。使用相同策略尝试制备Gal(α, 1→2)Gal和Gal(α, 1→3)Gal二糖糖苷，但使用2,3,4,6 - 四 - O - 苄基 - D - 吡喃半乳糖的1 - 三氯乙酰亚胺酯或1 - N - 甲基乙酰亚胺酯作为糖基供体。后一种亚胺酯产生了以Gal(α, 1→2)Gal和Gal(α, 1→3)Gal衍生物为主的混合物，但前一种得到了以Gal(β, 1→2)Gal异构体为主的产物。
