Ding Y, Labbe J, Kanie O, Hindsgaul O
Department of Chemistry, University of Alberta, Edmonton, Canada.
Bioorg Med Chem. 1996 May;4(5):683-92. doi: 10.1016/0968-0896(96)00064-8.
A single reaction of an unprotected beta-D-GlcNAc glycoside with tetra-O-acetyl-alpha-D-galactopyranosyl trichloroacetimidate in dioxane, catalyzed by BF3-etherate, was shown to yield all six possible Gal-GlcNAc disaccharides. This result is surprising not only because significant amounts of alpha-linked disaccharides were formed, despite the presence of a participating group at O-2 of the glycosyl donor, but also because glycosylation of the primary OH-6 is not the dominant reaction. These results suggest 'random-glycosylation' to be a valid strategy for the rapid production of oligosaccharide libraries.
在二氧六环中，以三氟化硼乙醚络合物为催化剂，未保护的β-D-氨基葡萄糖苷与四-O-乙酰-α-D-吡喃半乳糖基三氯乙酰胺进行单反应，结果表明生成了所有六种可能的半乳糖-氨基葡萄糖二糖。这一结果令人惊讶，不仅是因为尽管糖基供体的O-2位存在参与基团，但仍形成了大量α-连接的二糖，还因为伯羟基-6的糖基化不是主要反应。这些结果表明“随机糖基化”是快速构建寡糖文库的有效策略。
