2-(3'-mercaptopropionylamido)ethyl β-D-galactopyranosyl-(1->3)-O-2-acetamido-2-deoxy-β-D-glucopyranoside | 189324-48-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3'-mercaptopropionylamido)ethyl β-D-galactopyranosyl-(1->3)-O-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[2-[(2R,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyethyl]-4-sulfanylbutanamide
• CAS: 189324-48-9
• 化学式: C₂₀H₃₆N₂O₁₂S
• 分子量: 528.578
• InChiKey: VCKUYVKXGZPDLZ-DWCRUEOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  218
• 氢给体数：
  9
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-巯基乙醇 、 2-(3'-mercaptopropionylamido)ethyl β-D-galactopyranosyl-(1->3)-O-2-acetamido-2-deoxy-β-D-glucopyranoside 在 Thiopyridyl-activated Thiopropyl Sepharose 6B gel 作用下， 以 水 、 重水 为溶剂， 反应 16.0h， 生成 N-{2-[(2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-4-(2-hydroxy-ethyldisulfanyl)-butyramide
  参考文献：
  名称：

  Solid-Phase Enzymatic Synthesis of a Lewis a Trisaccharide Using an Acceptor Reversibly Bound to Sepharose

  摘要：

  The disaccharide 2-aminoethyl O-beta-D-galactopyranosyl-(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyranoside was reacted with thiobutyrolactone to give a disaccharide with a thiol group on the aglycone. This disaccharide was reacted with activated Thiopropyl Sepharose, which gave a disaccharide bound to Sepharose via a disulphide bond. Enzymatic fucosylation, using GDP-fucose and partially purified human milk fucosyltransferase, gave a trisaccharide in good yield, which was cleaved from Sepharose by treatment with mercaptoethanol or dithiothreitol.

  DOI：

  10.1080/07328309708006516
• 作为产物：
  描述：

  N-[(4aR,6R,7R,8R,8aS)-6-(2-Azido-ethoxy)-8-((2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 在 palladium on activated charcoal 氢气 、 碳酸氢钠 、 1,4-二巯基-2,3-丁二醇 作用下， 以 乙醇 、 水 为溶剂， 生成 2-(3'-mercaptopropionylamido)ethyl β-D-galactopyranosyl-(1->3)-O-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Solid-Phase Enzymatic Synthesis of a Lewis a Trisaccharide Using an Acceptor Reversibly Bound to Sepharose

  摘要：

  The disaccharide 2-aminoethyl O-beta-D-galactopyranosyl-(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyranoside was reacted with thiobutyrolactone to give a disaccharide with a thiol group on the aglycone. This disaccharide was reacted with activated Thiopropyl Sepharose, which gave a disaccharide bound to Sepharose via a disulphide bond. Enzymatic fucosylation, using GDP-fucose and partially purified human milk fucosyltransferase, gave a trisaccharide in good yield, which was cleaved from Sepharose by treatment with mercaptoethanol or dithiothreitol.

  DOI：

  10.1080/07328309708006516