N-(benzyloxycarbonyl)glycylglycylglycyl-L-serine methyl ester | 97347-10-9

• 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: N-(benzyloxycarbonyl)glycylglycylglycyl-L-serine methyl ester
• CAS: 97347-10-9
• 化学式: C₁₈H₂₄N₄O₈
• 分子量: 424.411
• InChiKey: PMWBYARQVKJEBZ-ZDUSSCGKSA-N

物化性质

• 沸点：
  847.7±65.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  172.16
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)glycylglycylglycyl-L-serine methyl ester 在 三乙胺 作用下， 以 甲醇 为溶剂， 以93.2%的产率得到N-(benzyloxycarbonyl)glycylglycylglycyl-L-serine
  参考文献：
  名称：

  Synthesis of N-glycopeptides and a neoglycoprotein

  摘要：

  O-(alpha-D-Glucopyranosyl)-(1----6)-O-beta-D-glucopyranosyl-(1----6)-1-N -(glycylglycylglycyl-L-seryl-L-leucyl-L-glutam-5-oyl)-alpha- D -glucopyranosylamine has been prepared, as a model of a derivative possibly present in the glomerular basement membrane of rats, by condensation of the corresponding L-glutamyl derivative of the trisaccharide with the pentapeptide in the presence of O,O-diethyl cyanophosphonate. Protective groups were removed by O-deacetylation, deethoxylation, and hydrogenolysis. The glutamyl derivative of the trisaccharide was also converted into the acyl azide which was condensed with bovine serum albumin to form a neoglycoprotein.

  DOI：

  10.1016/0008-6215(85)90014-x
• 作为产物：
  描述：

  N-benzyloxycarbonylglycylglycylglycyne methyl ester 在 氰基磷酸二乙酯 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 N-(benzyloxycarbonyl)glycylglycylglycyl-L-serine methyl ester
  参考文献：
  名称：

  Synthesis of N-glycopeptides and a neoglycoprotein

  摘要：

  O-(alpha-D-Glucopyranosyl)-(1----6)-O-beta-D-glucopyranosyl-(1----6)-1-N -(glycylglycylglycyl-L-seryl-L-leucyl-L-glutam-5-oyl)-alpha- D -glucopyranosylamine has been prepared, as a model of a derivative possibly present in the glomerular basement membrane of rats, by condensation of the corresponding L-glutamyl derivative of the trisaccharide with the pentapeptide in the presence of O,O-diethyl cyanophosphonate. Protective groups were removed by O-deacetylation, deethoxylation, and hydrogenolysis. The glutamyl derivative of the trisaccharide was also converted into the acyl azide which was condensed with bovine serum albumin to form a neoglycoprotein.

  DOI：

  10.1016/0008-6215(85)90014-x