O-α-D-glucopyranosyl-(1-6)-O-β-D-glucopyranosyl-(1-6)-1-N-(glycylglycylglycyl-L-seryl-L-leucyl-L-glutam-5-oyl)-α-D-glucopyranosylamine | 97347-04-1

• 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: O-α-D-glucopyranosyl-(1-6)-O-β-D-glucopyranosyl-(1-6)-1-N-(glycylglycylglycyl-L-seryl-L-leucyl-L-glutam-5-oyl)-α-D-glucopyranosylamine
• CAS: 97347-04-1
• 化学式: C₃₈H₆₅N₇O₂₄
• 分子量: 1003.97
• InChiKey: WTHUGSALEPIXSZ-OCZZUGOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11.9
• 重原子数：
  69.0
• 可旋转键数：
  25.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  506.6
• 氢给体数：
  19.0
• 氢受体数：
  24.0

反应信息

• 作为产物：
  描述：

  O-α-D-glucopyranosyl-(1-6)-O-β-D-glucopyranosyl-(1-6)-1-N--α-D-glucopyranosylamine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以82%的产率得到O-α-D-glucopyranosyl-(1-6)-O-β-D-glucopyranosyl-(1-6)-1-N-(glycylglycylglycyl-L-seryl-L-leucyl-L-glutam-5-oyl)-α-D-glucopyranosylamine
  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