2-(trimethylsilyl)ethyl (2-amino-2-deoxy-α-D-galactopyranosyl)-(1->4)-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl (2-amino-2-deoxy-α-D-galactopyranosyl)-(1->4)-β-D-galactopyranoside
• 英文别名: GalN(a1-4)Gal(b)-O-EtTMS；(2R,3R,4R,5R,6R)-5-amino-6-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-2-(hydroxymethyl)oxane-3,4-diol
• 化学式: C₁₇H₃₅NO₁₀Si
• 分子量: 441.551
• InChiKey: OBTZTNROAJWCCM-MJPBKBJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.07
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  184
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-(三甲基硅烷基)乙基beta-吡喃半乳糖苷 在 palladium on activated charcoal 吡啶 、 盐酸 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 甲醇 、 乙醇 、 丙酮 、 甲苯 为溶剂， -78.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 生成 2-(trimethylsilyl)ethyl (2-amino-2-deoxy-α-D-galactopyranosyl)-(1->4)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of some amino and carboxy analogs of galabiose; evaluation as inhibitors of the pilus protein PapGJ96 from Escherichia coli

  摘要：

  The 2'-amino-2'-deoxy, 6-amino-6-deoxy, and 6-carboxy analogs of the reference inhibitor 2-(trimethylsilyl)ethyl (alpha-D-galactopyranosyl)-(1-->4)-beta-D-galactopyranoside were synthesized and evaluated as inhibitors of the binding of the Escherichia coli-derived pilus protein PapG(J96), using an ELISA assay. The inhibitory efficiencies (K-rel; relative to the reference inhibitor) were: 157, 13, and < 8, respectively. The results support the previously proposed combining site model, where the protein carries a negatively charged amino acid residue near HO-2' and HO-6 of the galabioside. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00020-2