5-aminopentyl β-D-galactopyranosyl-(1→3)-2-deoxy-2-acetoamido-β-D-galactopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside | 1363157-95-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-aminopentyl β-D-galactopyranosyl-(1→3)-2-deoxy-2-acetoamido-β-D-galactopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside
• 英文别名: 5-aminopentyl (β-D-galactopyranosyl)-(1->3)-(2-acetamido-2-O-deoxy-β-D-glucopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside
• CAS: 1363157-95-2
• 化学式: C₃₁H₅₆N₂O₂₁
• 分子量: 792.786
• InChiKey: RFRUHGLADOXIMT-YAOHVLBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.45
• 重原子数：
  54.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  371.72
• 氢给体数：
  14.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  CMP-Neu5Ac 、 5-aminopentyl β-D-galactopyranosyl-(1→3)-2-deoxy-2-acetoamido-β-D-galactopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside 在 α(2,3)-sialyltransferase from Pasturella multocida 、 alkaline phosphatase 作用下， 以 aq. buffer 为溶剂， 反应 15.5h， 以79%的产率得到(2S,4S,5R,6R)-5-acetamido-2-[(2R,3R,4S,5S,6R)-2-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-(5-aminopentoxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
  参考文献：
  名称：

  Combination of automated solid-phase and enzymatic oligosaccharide synthesis provides access to α(2,3)-sialylated glycans

  摘要：

  一种合成策略结合了自动化固相化学合成和酶促唾液酸化，用于制备α（2,3）-唾液酸化的糖基。

  DOI：

  10.1039/c5cc01368b
• 作为产物：
  描述：

  5-azidopentyl (4,6-di-O-benzyl-β-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-O-deoxy-β-D-glucopyranosyl)-(1->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 甲酸 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以93%的产率得到5-aminopentyl β-D-galactopyranosyl-(1→3)-2-deoxy-2-acetoamido-β-D-galactopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside
  参考文献：
  名称：

  Acyl and Silyl Group Effects in Reactivity-Based One-Pot Glycosylation: Synthesis of Embryonic Stem Cell Surface Carbohydrates Lc₄ and IV²Fuc-Lc₄

  摘要：

  Relative reactivity evaluations showed the graded arming of toluenyl thioglucosides by variously positioned silyl groups but not by their acyl counterparts. These findings were applied in reactivity-based one-pot assembly of linker-attached Lc(4) and IV(2)Fuc-Lc(4), which are components of human embryonic stem cell surface. The sugar-galectin-1 binding was also examined.

  DOI：

  10.1021/ja300284x

文献信息

• Automated Glycan Assembly of Complex Oligosaccharides Related to Blood Group Determinants
  作者：Heung Sik Hahm、Chien-Fu Liang、Chian-Hui Lai、Richard J. Fair、Frank Schuhmacher、Peter H. Seeberger

  DOI：10.1021/acs.joc.6b00554

  日期：2016.7.15

  Lactotetraosyl (Lc4) and neo-lactotetraosyl (nLc4) are backbones that are common to many glycans. Using automated glycan assembly, these common core structures were constructed and elaborated to access synthetically challenging glycans of biological relevance. The incorporation of alpha-fucoses is demonstrated for H-type I and II; alpha(1,3)-galactose epitopes were prepared, and the pentasaccharide HNK-1 required incorporation of a 3-O-sulfate. In addition to preparing the target structures, essential insights were gained regarding the relationships of glycosylating agents and nucleophiles as well as the linker stability.