Neoglycolipid probes prepared via oxime ligation for microarray analysis of oligosaccharide-protein interactions

作者：Liu Yan; Feizi Ten^*; Carnpanero Rhodes Maria A; Childs Robert A; Zhang Yibing; Muiioy Barbara; Evans Philip G; O**orn Helen M I; Otto Diana; Crocker Paul R; Chai Wengang

来源：Chemistry & Biology, 2007, 14(7): 847-859.

DOI：10.1016/j.chembiol.2007.06.009

Neoglycolipid technology is the basis of a microarray platform for assigning oligosaccharide ligands for carbohydrate-binding proteins. The strategy for generating the neoglycolipid probes by reductive amination results in ring opening of the core monosaccharides. This often limits applicability to short-chain saccharides, although the majority of recognition motifs are satisfactorily presented with neoglycolipids of longer oligosaccharides. Here, we describe neoglycolipids prepared by oxime ligation. We provide evidence from NMR studies that a significant proportion of the oxime-linked core monosaccharide is in the ring-closed form, and this form selectively interacts with a carbohydrate-binding protein. By microarray analyses we demonstrate the effective presentation with oxime-linked neoglycolipids of (1) Lewis(x) trisaccharide to antibodies to Lewisx, (2) sialyllactose analogs to the sialic acid-binding receptors, siglecs, and (3) N-glycans to a plant lectin that requires an intact N-acetylglucosamine core.

• 出版日期2007-7
• 单位中国食品药品检定研究院