Karelin A A, Tsvetkov Iu E, Kogan G, Bystritski S, Nifant'ev N E
Bioorg Khim. 2007 Jan-Feb;33(1):119-30. doi: 10.1134/s106816200701013x.
3-Aminopropyl glycosides of alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyra-nosyl-(1-->2)-alpha-D-mannopyranose, alpha-D-mannopyranosyl-(1-->3)-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(l -- 2)-alpha-D-mannopyranose, and alpha-D-mannopyranosyl-(1-->2)-[alpha-D-mannopyranosyl-(1-->3)]-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranose were efficiently synthesized starting from ethyl 2-O-acetyl(benzoyl)-3,4,6-tri-O-benzyl-l-thio-alpha-D-mannopyranoside, ethyl 4,6-di-O-benzyl-2-O-benzoyl-1-thio-alpha-D-mannopyranoside, ethyl 4,6-di-O-benzyl-2,3-di-O-benzoyl-l-thio-alpha-D-mannopyranoside, and 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl bromide. The oligosaccharide chains synthesized correspond to the three structural types of side chains of mannan from Candida albicans cell wall. A conjugate of the third pentasaccharide with bovine serum albumin was prepared using the squarate method.
α-D-甘露吡喃糖基-(1→2)-α-D-甘露吡喃糖基-(1→2)-α-D-甘露吡喃糖基-(1→2)-α-D-甘露吡喃糖、α-D-甘露吡喃糖基-(1→3)-α-D-甘露吡喃糖基-(1→2)-α-D-甘露吡喃糖基-(1→2)-α-D-甘露吡喃糖以及α-D-甘露吡喃糖基-(1→2)-[α-D-甘露吡喃糖基-(1→3)]-α-D-甘露吡喃糖基-(1→2)-α-D-甘露吡喃糖基-(1→2)-α-D-甘露吡喃糖的3-氨基丙基糖苷，以2-O-乙酰基（苯甲酰基）-3,4,6-三-O-苄基-α-D-甘露吡喃糖硫苷乙酯、4,6-二-O-苄基-2-O-苯甲酰基-α-D-甘露吡喃糖硫苷乙酯、4,6-二-O-苄基-2,3-二-O-苯甲酰基-α-D-甘露吡喃糖硫苷乙酯和2,3,4,6-四-O-苯甲酰基-α-D-甘露吡喃糖溴化物为起始原料高效合成。合成的寡糖链对应白色念珠菌细胞壁甘露聚糖侧链的三种结构类型。使用方酸法制备了第三种五糖与牛血清白蛋白的缀合物。
