Nα-(3-carboxy-1-oxopropyl)-Nε-(benzyloxycarbonyl)-L-lysine | 797761-53-6

• 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-lysine
• 英文别名: N^α-(3-carboxy-1-oxopropyl)-N^ε-(benzyloxycarbonyl)-L-lysine
• CAS: 797761-53-6
• 化学式: C₁₈H₂₄N₂O₇
• 分子量: 380.398
• InChiKey: HEBORUACFGFAMR-AWEZNQCLSA-N

物化性质

• 沸点：
  720.2±60.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  27.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  142.03
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  丁二酸酐 、 N6-Cbz-L-赖氨酸 以 甲醇 为溶剂， 反应 12.0h， 以86%的产率得到Nα-(3-carboxy-1-oxopropyl)-Nε-(benzyloxycarbonyl)-L-lysine
  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