4-(((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)butanal | 1234547-17-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-(((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)butanal
• CAS: 1234547-17-1
• 化学式: C₁₆H₂₈O₁₂
• 分子量: 412.391
• InChiKey: ZQTXDRVWUWDVJF-FZVFFMNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.39
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  195.6
• 氢给体数：
  7.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  4-pentenyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside 在 二甲基硫 、 臭氧 作用下， 以 甲醇 为溶剂， 以100%的产率得到4-(((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)butanal
  参考文献：
  名称：

  Synthesis of Galabiose-chitosan Conjugate as Potent Inhibitor of Streptococcus suis Adhesion

  摘要：

  The aim of this work is to construct a safe and effective drug candidate against Streptococcus suis infection. A panel of chitosan-based polymer conjugates with branched galabiose (Gal alpha 1-4Gal) side chains was synthesized as inhibitors of S. suis adhesion. The synthesis was achieved by using an aldehyde-functionalized galabiose derivative to graft it onto chitosan amino groups. Structural compositions of the conjugates were verified by (1)H NMR spectroscopy and CHN elemental analyses. Potent inhibitory activities of the conjugates against S. suis adhesion to human erythrocytes were determined at low nanomolar concentration by HAI assay. An SPR study revealed a high affinity binding (K(d) = 39.6 nM) of the conjugate with BSI-B(4) lectin. By using biocompatible chitosan as the scaffold for presenting S. suis-specific galabiose units, as well as the concise route tailored for the conjugate syntheses, the present study provides a practical way for explorations of new anti-S. suis therapies.

  DOI：

  10.1021/bm100289v