用于探索糖基转移酶底物特异性的Hexp-(1→4)-β-D-GlcpNAc-(1→2)-α-D-Manp-(1→O)(CH₂)₇CH₃探针的合成：第二部分，Hex = 3-O-甲基-β-D-半乳糖、3-脱氧-β-D-半乳糖、3-脱氧-3-氟-β-D-半乳糖、3-氨基-3-脱氧-β-D-半乳糖、β-D-古洛糖、α-L-阿洛糖或β-L-半乳糖。
Synthesis of Hexp-(1-->4)-beta-D-GlcpNAc-(1-->2)-alpha-D-Manp-(1-->O) (CH2)7 CH3 probes for exploration of the substrate specificity of glycosyltransferases: Part II, Hex = 3-O-methyl-beta-D-Gal, 3-deoxy-beta-D-Gal, 3-deoxy-3-fluoro-beta-D-Gal, 3-amino-3-deoxy-beta-D-Gal, beta-D-Gul, alpha-L-Alt, or beta-L-Gal.
作者信息
van Dorst J A, van Heusden C J, Tikkanen J M, Kamerling J P, Vliegenthart J F
机构信息
Department of Bio-Organic Chemistry, Utrecht University, The Netherlands.
出版信息
Carbohydr Res. 1997 Jan 17;297(3):209-27. doi: 10.1016/s0008-6215(96)00266-2.
Seven analogues of the trisaccharide beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->2)-alpha-D-Manp-(1-->O)(CH 2)7CH3 have been synthesized as potential substrates for glycosyltransferases involved in the chain-termination of N-acetyllactosamine-type N-glycans. These compounds include: 3-O-methyl-beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->2)-alpha-D-Manp -(1-->O) (CH2)7CH3, 3-deoxy-beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->2)-alpha-D-Manp-(1 -->O) (CH2)7CH3, 3-deoxy-3-fluoro-beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->2)-alpha-D-M anp- (1-->O)(CH2)7Ch3, 3-amino-3-deoxy-beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->2)-alpha-D-Ma np- (1-->O)(CH2)7CH3, beta-D-Gulp-(1-->4)-beta-D-GlcpNAc-(1-->2)-alpha-D-Manp-(1-- >O)(CH2)7CH3, beta-L-Galp-(1-->4)-beta-D-GlcpNAc-(1-->2)-alpha-D-Manp-(1-->O)(CH 2)7CH3, and alpha-L-Altp-(1-->4)-beta-D-GlcpNAc-(1-->2)-alpha-D-Manp-(1- ->O) (CH2)7CH3. All trisaccharides were obtained by condensation of suitably modified glycosyl donors based on imidates or thioglycosides with the same disaccharide acceptor, octyl 3,4,6-tri-O-benzyl-2-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D- glucopyranosyl)-alpha-D-mannopyranoside, followed by deprotection.
已合成了七种三糖β-D-半乳糖基-(1→4)-β-D-葡萄糖胺基-(1→2)-α-D-甘露糖基-(1→O)(CH₂)₇CH₃的类似物，作为参与N-乙酰乳糖胺型N-聚糖链终止的糖基转移酶的潜在底物。这些化合物包括：3-O-甲基-β-D-半乳糖基-(1→4)-β-D-葡萄糖胺基-(1→2)-α-D-甘露糖基-(1→O)(CH₂)₇CH₃、3-脱氧-β-D-半乳糖基-(1→4)-β-D-葡萄糖胺基-(1→2)-α-D-甘露糖基-(1→O)(CH₂)₇CH₃、3-脱氧-3-氟-β-D-半乳糖基-(1→4)-β-D-葡萄糖胺基-(1→2)-α-D-甘露糖基-(1→O)(CH₂)₇CH₃、3-氨基-3-脱氧-β-D-半乳糖基-(1→4)-β-D-葡萄糖胺基-(1→2)-α-D-甘露糖基-(1→O)(CH₂)₇CH₃、β-D-古洛糖基-(1→4)-β-D-葡萄糖胺基-(1→2)-α-D-甘露糖基-(1→O)(CH₂)₇CH₃、β-L-半乳糖基-(1→4)-β-D-葡萄糖胺基-(1→2)-α-D-甘露糖基-(1→O)(CH₂)₇CH₃和α-L-阿洛糖基-(1→4)-β-D-葡萄糖胺基-(1→2)-α-D-甘露糖基-(1→O)(CH₂)₇CH₃。所有三糖均通过基于亚氨酸酯或硫代糖苷的适当修饰的糖基供体与相同的二糖受体3,4,6-三-O-苄基-2-O-(3,6-二-O-苄基-2-脱氧-2-邻苯二甲酰亚胺基-β-D-吡喃葡萄糖基)-α-D-甘露吡喃糖苷缩合，然后脱保护得到。
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