2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<6-O-acetyl-2-amino-2-deoxy-3-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1''<*>2'-lactam)-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranos)> | 168139-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<6-O-acetyl-2-amino-2-deoxy-3-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1''<*>2'-lactam)-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranos)>
• CAS: 168139-46-6
• 化学式: C₅₈H₈₅N₃O₃₃Si
• 分子量: 1380.4
• InChiKey: VWPNBUAFRGYPND-YXYDZTJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.56
• 重原子数：
  95.0
• 可旋转键数：
  27.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  450.44
• 氢给体数：
  3.0
• 氢受体数：
  33.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<6-O-acetyl-2-amino-2-deoxy-3-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1''<*>2'-lactam)-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranos)> 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2-(trimethylsilyl)ethyl 4-O-<2-amino-2-deoxy-3-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1''<*>2'-lactam)-4-O-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Ganglioside Lactams Corresponding to GM1-, GM2-, GM3-, and GM4-Ganglioside Lactones

  摘要：

  Ganglioside lactams are potentially useful analogs of ganglioside lactones, which are highly immunogenic derivatives of gangliosides. The lactam corresponding to the G(M3)-lactone saccharide has been synthesized by sialylation of a suitably protected lactose derivative carrying an azido group in the 2'-position, followed by reduction and ring closure to form G(M3)-lactam. Glycosylation in the 4-position of the central saccharide unit gave the G(M2)- and G(M1)- lactam saccharides. By a similar route, a 2-azido-Gal derivative was sialylated and treated as above to give the G(M4)-lactam saccharide. Deprotection gave the G(M2-4)-lactam saccharides in water soluble form, whereas attempted deprotection of the G(M1)-lactam caused its degradation. The G(M3)-lactam saccharide was coupled to ceramide, to afford the ganglioside lactam analog, and via a spacer to bovine serum albumin (BSA). The BSA conjugate was used as immunogen to raise monoclonal antibodies that cross-reacted with G(M3)-lactone. The antibodies were used in a histological staining of murine melanoma cells, clearly showing the presence of G(M3)-lactone on the cell surface. Keeping the G(M2-4)-lactam saccharides in D2O at 37 degrees C for 1 month caused marginal (0-11%) hydrolysis of the lactam ring.

  DOI：

  10.1021/ja00122a002
• 作为产物：
  描述：

  乙酸酐 、 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<6-O-acetyl-2-amino-2-deoxy-3-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1''<*>2'-lactam)-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranos)>
  参考文献：
  名称：

  Synthesis of Ganglioside Lactams Corresponding to GM1-, GM2-, GM3-, and GM4-Ganglioside Lactones

  摘要：

  Ganglioside lactams are potentially useful analogs of ganglioside lactones, which are highly immunogenic derivatives of gangliosides. The lactam corresponding to the G(M3)-lactone saccharide has been synthesized by sialylation of a suitably protected lactose derivative carrying an azido group in the 2'-position, followed by reduction and ring closure to form G(M3)-lactam. Glycosylation in the 4-position of the central saccharide unit gave the G(M2)- and G(M1)- lactam saccharides. By a similar route, a 2-azido-Gal derivative was sialylated and treated as above to give the G(M4)-lactam saccharide. Deprotection gave the G(M2-4)-lactam saccharides in water soluble form, whereas attempted deprotection of the G(M1)-lactam caused its degradation. The G(M3)-lactam saccharide was coupled to ceramide, to afford the ganglioside lactam analog, and via a spacer to bovine serum albumin (BSA). The BSA conjugate was used as immunogen to raise monoclonal antibodies that cross-reacted with G(M3)-lactone. The antibodies were used in a histological staining of murine melanoma cells, clearly showing the presence of G(M3)-lactone on the cell surface. Keeping the G(M2-4)-lactam saccharides in D2O at 37 degrees C for 1 month caused marginal (0-11%) hydrolysis of the lactam ring.

  DOI：

  10.1021/ja00122a002