8-methoxycarbonyloctyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->3)-2-deoxy-2-(methyl β-D-galactopyranosyluronamide)-β-D-glucopyranoside | 219727-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-methoxycarbonyloctyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->3)-2-deoxy-2-(methyl β-D-galactopyranosyluronamide)-β-D-glucopyranoside
• CAS: 219727-31-8
• 化学式: C₄₀H₆₈N₂O₂₆
• 分子量: 992.978
• InChiKey: NBMBZAQNURMDJB-MFTDDCBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.72
• 重原子数：
  68.0
• 可旋转键数：
  24.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  438.4
• 氢给体数：
  15.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  GDP-fucose 、 8-methoxycarbonyloctyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->3)-2-deoxy-2-(methyl β-D-galactopyranosyluronamide)-β-D-glucopyranoside 在 sodium cacodylate 、 manganese(ll) chloride 作用下， 以 水 为溶剂， 反应 24.0h， 以63%的产率得到8-methoxycarbonyloctyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->3)-[α-L-fucopyranosyl-(1->4)]-2-deoxy-2-(methyl β-D-galactopyranosyluronamide)-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosyltransferase catalyzed assemblage of sialyl-Lewisa-saccharopeptides

  摘要：

  A series of methyl hexopyranosiduronic acids are coupled to type I disaccharide amines to give 'trisaccharides' which have the natural N-acetyl group of the type I disaccharides replaced by uronic acids (--> saccharopeptides). These saccharopeptides are surprisingly good substrates for alpha-2,3-sialyltransferase and fucosyltransferase III. The enzymes transfer N-acetylneuraminic acid and fucose, respectively, onto these acceptor substrates, despite the far reaching alterations, regio- and stereospecifically in the expected manner to yield sialyl-Lewis(a)-saccharopeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00229-8
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 甲醇 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium methylate 、 O-Benzotriazol-1-yl-N,N,N',N'-bis(tetramethylene)uronium hexafluorophosphate 、 三乙胺 、 sodium bromide 、 manganese(ll) chloride 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 8-methoxycarbonyloctyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->3)-2-deoxy-2-(methyl β-D-galactopyranosyluronamide)-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosyltransferase catalyzed assemblage of sialyl-Lewisa-saccharopeptides

  摘要：

  A series of methyl hexopyranosiduronic acids are coupled to type I disaccharide amines to give 'trisaccharides' which have the natural N-acetyl group of the type I disaccharides replaced by uronic acids (--> saccharopeptides). These saccharopeptides are surprisingly good substrates for alpha-2,3-sialyltransferase and fucosyltransferase III. The enzymes transfer N-acetylneuraminic acid and fucose, respectively, onto these acceptor substrates, despite the far reaching alterations, regio- and stereospecifically in the expected manner to yield sialyl-Lewis(a)-saccharopeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00229-8