Nα-(3-carboxy-1-oxopropyl)-Nε-(benzyloxycarbonyl)-L-lysyl-L-glutamic acid tris(pentafluorophenyl)ester | 797761-61-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Nα-(3-carboxy-1-oxopropyl)-Nε-(benzyloxycarbonyl)-L-lysyl-L-glutamic acid tris(pentafluorophenyl)ester
• 英文别名: N^α-(3-carboxy-1-oxopropyl)-N^ε-(benzyloxycarbonyl)-L-lysyl-L-glutamic acid tris(pentafluorophenyl)ester
• CAS: 797761-61-6
• 化学式: C₄₁H₂₈F₁₅N₃O₁₀
• 分子量: 1007.66
• InChiKey: NVASNGYEZRXHJJ-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  69.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  175.43
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-aminopropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 、 Nα-(3-carboxy-1-oxopropyl)-Nε-(benzyloxycarbonyl)-L-lysyl-L-glutamic acid tris(pentafluorophenyl)ester 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以85%的产率得到N^α-[8-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxyl)-5-aza-1,4-dioxooctyl]-N^ε-(benzyloxycarbonyl)-L-lysyl-N-bis[3-(2-acetamido-3,4,6-tri-O-acetyl-β-D-glucopyranosyloxyl)propyl]-L-glutamamide
  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：

  N6-Cbz-L-赖氨酸 在 吡啶 、 N-羟基丁二酰亚胺 、 四(三苯基膦)钯 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 N-甲基苯胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.5h， 生成 Nα-(3-carboxy-1-oxopropyl)-Nε-(benzyloxycarbonyl)-L-lysyl-L-glutamic acid tris(pentafluorophenyl)ester
  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