2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranose | 684269-07-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranose
• 英文别名: Bz(-3)[Bz(-4)][Bz(-6)]Man2Ac(a1-2)[Bz(-3)][Bz(-4)][Bz(-6)]a-Man；[(2R,3R,4S,5S,6S)-5-[(2R,3S,4S,5R,6R)-3-acetyloxy-4,5-dibenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxy-3,4-dibenzoyloxy-6-hydroxyoxan-2-yl]methyl benzoate
• CAS: 684269-07-6
• 化学式: C₅₆H₄₈O₁₈
• 分子量: 1008.99
• InChiKey: PIPXLSCCXGQAKB-PCINIVGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  74.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  232.02
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  三氯乙腈 、 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以473 mg的产率得到2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  来自小孢子菌属植物的真菌细胞壁多糖的甘露糖三糖和四糖重复单元的简便合成

  摘要：

  摘要 三糖 α-D-吡喃甘露糖基-(1→2)-α-D-吡喃甘露糖基-(1→6)-α-D-吡喃甘露糖和四糖 α-D-吡喃甘露糖基-(1→2) 的简便合成-α-D-吡喃甘露糖基-(1→6)-α-D-吡喃甘露糖基-(1→6)-D-吡喃甘露糖是来自石膏小孢子菌和毛癣菌的真菌细胞壁多糖的重复单元，使用α-( 1→2)-连接的二糖亚胺酸酯作为供体。二糖亚氨酸酯由 3,4,6-tri-O-benzoyl-1,2-O-allyloxyethylidene-β-D-mannopyranose 的自缩合制备。

  DOI：

  10.1081/scc-120003613
• 作为产物：
  描述：

  phenyl 3,4,6-tri-O-benzoyl-1-thio-α-D-mannopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.5h， 生成 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranose
  参考文献：
  名称：

  Convergent Synthesis of Homogeneous Glc₁Man₉GlcNAc₂-Protein and Derivatives as Ligands of Molecular Chaperones in Protein Quality Control

  摘要：

  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.

  DOI：

  10.1021/ja204831z

文献信息

• Zhu; Kong, Synlett, 2000, # 12, p. 1783 - 1787
  作者：Zhu、Kong

  DOI：——

  日期：——