N-{3-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]propyl}-Nα-{8-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]-5-aza-1,4-dioxooctyl}-Nε-(benzyloxycarbonyl)-L-lysinamide | 797761-57-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-{3-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]propyl}-Nα-{8-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]-5-aza-1,4-dioxooctyl}-Nε-(benzyloxycarbonyl)-L-lysinamide
• 英文别名: N-{3-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]propyl}-N^α-{8-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]-5-aza-1,4-dioxooctyl}-N^ε-(benzyloxycarbonyl)-L-lysinamide
• CAS: 797761-57-0
• 化学式: C₅₂H₈₄N₆O₂₇
• 分子量: 1225.26
• InChiKey: WKPHDIUDXSOKML-QWZWDNERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.07
• 重原子数：
  85.0
• 可旋转键数：
  32.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  500.43
• 氢给体数：
  18.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 N-{3-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]propyl}-Nα-{8-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]-5-aza-1,4-dioxooctyl}-Nε-(benzyloxycarbonyl)-L-lysinamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 以92%的产率得到N-{3-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]propyl}-N^α-{8-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]-5-aza-1,4-dioxooctyl}-L-lysinamide, monoacetic acid
  参考文献：
  名称：

  Glycoinsulins:  Dendritic Sialyloligosaccharide-Displaying Insulins Showing a Prolonged Blood-Sugar-Lowering Activity

  摘要：

  Mono-, di-, and trisialyloligosaccharides were introduced to mutant insulins through enzymatic reactions. Sugar chains were sialylated by alpha2,6-sialyltransferase (alpha2,6-SiaT) via an accessible glutamine residue at the N-terminus of the B-chain attached by transglutaminase (TGase). Sia2,6-di-LacNAc-Ins(B-F1Q) and Sia2,6-tri-LacNAc-Ins(B-F1Q), displaying two and three sialyl-N-acetyllactosamines, respectively, were administered to hyperglycemic mice. Both branched glycoinsulins showed prolonged glucose-lowering effects compared to native or lactose-carrying insulins, showing that sialic acid is important in obtaining a prolonged effect. Sia2,6-tri-LacNAc-lns(B-F1Q), in particular, induced a significant delay in the recovery of glucose levels.

  DOI：

  10.1021/ja046426l
• 作为产物：
  描述：

  Nα-(3-carboxy-1-oxopropyl)-Nε-(benzyloxycarbonyl)-L-lysine 在 吡啶 、 β-1,4-galactosyltransferase 、 三乙胺 、 N,N-二异丙基乙胺 、 manganese(ll) chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 70.0h， 生成 N-{3-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]propyl}-Nα-{8-[2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyloxyl]-5-aza-1,4-dioxooctyl}-Nε-(benzyloxycarbonyl)-L-lysinamide
  参考文献：
  名称：

  Glycoinsulins:  Dendritic Sialyloligosaccharide-Displaying Insulins Showing a Prolonged Blood-Sugar-Lowering Activity

  摘要：

  Mono-, di-, and trisialyloligosaccharides were introduced to mutant insulins through enzymatic reactions. Sugar chains were sialylated by alpha2,6-sialyltransferase (alpha2,6-SiaT) via an accessible glutamine residue at the N-terminus of the B-chain attached by transglutaminase (TGase). Sia2,6-di-LacNAc-Ins(B-F1Q) and Sia2,6-tri-LacNAc-Ins(B-F1Q), displaying two and three sialyl-N-acetyllactosamines, respectively, were administered to hyperglycemic mice. Both branched glycoinsulins showed prolonged glucose-lowering effects compared to native or lactose-carrying insulins, showing that sialic acid is important in obtaining a prolonged effect. Sia2,6-tri-LacNAc-lns(B-F1Q), in particular, induced a significant delay in the recovery of glucose levels.

  DOI：

  10.1021/ja046426l