2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl fluoride | 107715-16-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl fluoride
• 英文别名: 2,3,6-Tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-glucopyranosyl fluoride；Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]a-Glc1F；(2R,3R,4S,5R,6R)-2-fluoro-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxane
• CAS: 107715-16-2
• 化学式: C₆₁H₆₃FO₁₀
• 分子量: 975.164
• InChiKey: OZAZEKZMSIQRJB-VVDHWLILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  72
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  溴甲苯 、 α-lactosyl fluoride 在 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Alkylation of Glycosyl Fluorides

  摘要：

  据报告，在温和的碱性条件下，未保护的糖基氟化物可以直接烷基化，且不影响其异构体。因此，在路易斯酸催化糖基化反应中应用的过烷基化糖基氟化物，现在可以通过两个简单的步骤从起始糖有效制备。

  DOI：

  10.1055/s-1988-27486

文献信息

• Convergent Synthesis of Homogeneous Glc₁Man₉GlcNAc₂-Protein and Derivatives as Ligands of Molecular Chaperones in Protein Quality Control
  作者：Mohammed N. Amin、Wei Huang、Rahman M. Mizanur、Lai-Xi Wang

  DOI：10.1021/ja204831z

  日期：2011.9.14

  A detailed understanding of the molecular mechanism of chaperone-assisted protein quality control is often hampered by the lack of well-defined homogeneous glycoprotein probes. We describe here a highly convergent chemoenzymatic synthesis of the monoglucosylated glycoforms of bovine ribonuclease (RNase) as specific ligands of lectin-like chaperones calnexin (CNX) and calreticulin (CRT) that are known to recognize the monoglucosylated high-mannose oligosaccharide component of glycoproteins in protein folding. The synthesis of a selectively modified glycoform Gal(1)Glc(1)Man(9)GlcNAc(2)-RNase was accomplished by chemical synthesis of a large N-glycan oxazoline and its subsequent enzymatic ligation to GlcNAc-RNase under the catalysis of a glycosynthase. Selective removal of the terminal galactose by a beta-galactosidase gave the Glc(1)Man(9)GlcNAc(2)-RNase glycoform in excellent yield. CD spectroscopic analysis and RNA-hydrolyzing assay indicated that the synthetic RNase glycoforms maintained essentially the same global conformations and were fully active as the natural bovine ribonudease B. SPR binding studies revealed that the Glc(1)Man(9)GlcNAc(2)-RNase had high affinity to lectin CRT, while the synthetic Man(9)GlcNAc(2)-RNase glycoform and natural RNase B did not show CRT-binding activity. These results confirmed the essential role of the glucose moiety in the chaperone molecular recognition. Interestingly, the galactose-masked glycoform Gal(1)Glc(1)Man(9)GlcNAc(2)-RNase also showed significant affinity to lectin CRT, suggesting that a galactose beta-1,4-linked to the key glucose moiety does not significantly block the lectin binding. These synthetic homogeneous glycoprotein probes should be valuable for a detailed mechanistic study on how molecular chaperones work in concert to distinguish between misfolded and folded glycoproteins in the protein quality control cycle.
• US4803263A
  申请人：——

  公开号：US4803263A

  公开（公告）日：1989-02-07
• Alkylation of Glycosyl Fluorides
  作者：Joachim Thiem、Matthias Wiesner

  DOI：10.1055/s-1988-27486

  日期：——

  A direct alkylation of unprotected glycosyl fluorides under mild basic conditions without affecting the anomeric group is reported. Thus peralkylated glycosyl fluorides, applied in Lewis acid catalyzed glycosylations, are now effectively available from the starting sugar in two simple steps.

  据报告，在温和的碱性条件下，未保护的糖基氟化物可以直接烷基化，且不影响其异构体。因此，在路易斯酸催化糖基化反应中应用的过烷基化糖基氟化物，现在可以通过两个简单的步骤从起始糖有效制备。