benzyl β-D-galactopyranosyl-(1->2)-[(β-D-galactopyranosyl-(1->3)]-β-D-galactopyranosyl-(1->6)-[β-D-galactofuranosyl-(1->4)]-2-acetamido-2-deoxy-α-D-glucopyranoside | 904297-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl β-D-galactopyranosyl-(1->2)-[(β-D-galactopyranosyl-(1->3)]-β-D-galactopyranosyl-(1->6)-[β-D-galactofuranosyl-(1->4)]-2-acetamido-2-deoxy-α-D-glucopyranoside
• CAS: 904297-06-9
• 化学式: C₃₉H₆₁NO₂₆
• 分子量: 959.904
• InChiKey: NJJHSVRBXTXIIY-PTIICVJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.56
• 重原子数：
  66.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  424.85
• 氢给体数：
  16.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  benzyl β-D-galactopyranosyl-(1->2)-[(β-D-galactopyranosyl-(1->3)]-β-D-galactopyranosyl-(1->6)-[β-D-galactofuranosyl-(1->4)]-2-acetamido-2-deoxy-α-D-glucopyranoside 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 5.0 ℃ 、202.65 kPa 条件下， 反应 21.0h， 生成 β-D-galactopyranosyl-(1->2)-[(β-D-galactopyranosyl-(1->3)]-β-D-galactopyranosyl-(1->6)-[β-D-galactofuranosyl-(1->4)]-2-acetamido-2-deoxy-D-glucitol
  参考文献：
  名称：

  Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase

  摘要：

  The mucin-like glycoproteins of Trypanosoma cruzi have novel O-linked oligosaccharides that are acceptors of sialic acid in the trans-sialidase (TcTS) reaction. The transference of sialic acid from host glycoconjugates to the mucins is involved in infection and pathogenesis. The synthesis of the pentasaccharide, beta-D-Galp-(1 -> 2)-[beta-D-Galp-(1 -> 43)]-beta-D-Galp-(1 -> 6)-[beta-D-Galf-(1 -> 4)]-D-GlcpNAc and the corresponding alditol, previously isolated by reductive beta-elimination of the mucins, is described. The key step was the 6-O-glycosylation of a easily accessible derivative of beta-D-Galf-(1 -> 4)-D-GlcpNAc with a beta-D-Galp-(1 -> 2)-[beta-D-Galp-(1 -> 3)]-D-Galp donor using the trichloroacetimidate method. The P-linkage was diastereoselectively obtained by the nitrile effect. The pentasaccharide is the major oligosaccharide in the mucins of T. cruzi, G strain and presents two terminal beta-D-Galp residues for possible sialylation by TcTS. A preparative sialylation reaction was performed with its benzyl glycoside and the sialylated product was isolated and characterized. NMR spectroscopic analysis showed that selective monosialylation occurred at the terminal (1 -> 3) linked galactopyranose. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.033
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到benzyl β-D-galactopyranosyl-(1->2)-[(β-D-galactopyranosyl-(1->3)]-β-D-galactopyranosyl-(1->6)-[β-D-galactofuranosyl-(1->4)]-2-acetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase

  摘要：

  The mucin-like glycoproteins of Trypanosoma cruzi have novel O-linked oligosaccharides that are acceptors of sialic acid in the trans-sialidase (TcTS) reaction. The transference of sialic acid from host glycoconjugates to the mucins is involved in infection and pathogenesis. The synthesis of the pentasaccharide, beta-D-Galp-(1 -> 2)-[beta-D-Galp-(1 -> 43)]-beta-D-Galp-(1 -> 6)-[beta-D-Galf-(1 -> 4)]-D-GlcpNAc and the corresponding alditol, previously isolated by reductive beta-elimination of the mucins, is described. The key step was the 6-O-glycosylation of a easily accessible derivative of beta-D-Galf-(1 -> 4)-D-GlcpNAc with a beta-D-Galp-(1 -> 2)-[beta-D-Galp-(1 -> 3)]-D-Galp donor using the trichloroacetimidate method. The P-linkage was diastereoselectively obtained by the nitrile effect. The pentasaccharide is the major oligosaccharide in the mucins of T. cruzi, G strain and presents two terminal beta-D-Galp residues for possible sialylation by TcTS. A preparative sialylation reaction was performed with its benzyl glycoside and the sialylated product was isolated and characterized. NMR spectroscopic analysis showed that selective monosialylation occurred at the terminal (1 -> 3) linked galactopyranose. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.033