sialyl Lewis X | 136514-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: sialyl Lewis X
• 英文别名: alpha-N-acetylneuraminic acid；sialyl Lewis(x)；(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-acetamido-6-hydroxy-2-(hydroxymethyl)-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 136514-66-4
• 化学式: C₃₁H₅₂N₂O₂₃
• 分子量: 820.753
• InChiKey: NIGUVXFURDGQKZ-UQTBNESHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.3
• 重原子数：
  56
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  403
• 氢给体数：
  15
• 氢受体数：
  23

反应信息

• 作为产物：
  描述：

  在 palladium dihydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 生成 sialyl Lewis X
  参考文献：
  名称：

  Azaglycosylation of complex stannyl alkoxides with glycal-derived iodo sulfonamides: a straightforward synthesis of sialyl-Lewis X antigen and other oligosaccharide domains

  摘要：

  DOI：

  10.1021/ja00047a078

文献信息

• Stereocontrolled synthesis of sialyl Lex, the oligosaccharide binding ligand to ELAM-1 (sialyl =N-acetylneuramin)
  作者：K. C. Nicolaou、C. W. Hummel、N. J. Bockovich、C.-H. Wong

  DOI：10.1039/c39910000870

  日期：——

  Sialyl Lex1 the oligosaccharide binding ligand to ELAM-1 is synthesized from building blocks 2–5via a short route featuring the principle of a neighbouring PhS group as an auxiliary to facilitate and stereochemically control the formation of the desired glycoside bond in the target molecule.

  唾液酸勒X 1寡糖结合配体到ELAM-1是由积木合成2 - 5经由设有一个相邻PHS团作为辅助的原理，以促进和立体化学控制期望的糖苷键的形成在目标上的短路线分子。
• Inhibitors of E-, P- and L-selectin binding
  申请人：The Scripps Research Institute

  公开号：US05830871A1

  公开（公告）日：1998-11-03

  Inhibitors of E-, P- and L-selectin binding are synthesized by an aldol addition reaction between a glycoside aldehyde precursor and dihydroxyacetone phosphate or a derivative thereof. The addition reaction is catalyzed by aldolase. The inhibitors exhibit an activity comparable to sialyl Lewis X with respect to the E-selectin binding assay and high activities in the P- and L-selectin binding assays. The inhibitors are employable for blocking neutrophil inflamatory conditions.

  E-, P- 和 L- 选择素结合的抑制剂是通过糖苷醛前体和二羟基丙酮磷酸盐或其衍生物之间的醛缩加反应合成的。醛缩加反应由醛缩酶催化。这些抑制剂在 E- 选择素结合试验中表现出与唾液酸 Lewis X 相当的活性，并且在 P- 和 L- 选择素结合试验中具有高活性。这些抑制剂可用于阻止中性粒细胞炎症病症。
• Azaglycosylation of complex stannyl alkoxides with glycal-derived iodo sulfonamides: a straightforward synthesis of sialyl-Lewis X antigen and other oligosaccharide domains
  作者：Samuel J. Danishefsky、Koshi Koseki、David A. Griffith、Jacquelyn Gervay、John M. Peterson、Frank E. McDonald、Takeshi Oriyama

  DOI：10.1021/ja00047a078

  日期：1992.10