N-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,5-dioxopyrrol-1-yl)acetamide | 333384-36-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,5-dioxopyrrol-1-yl)acetamide
• CAS: 333384-36-4
• 化学式: C₁₄H₁₉N₃O₈
• 分子量: 357.32
• InChiKey: PVSBPZSBWYXPDJ-ODTJPNJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  166
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  谷胱甘肽 、 N-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,5-dioxopyrrol-1-yl)acetamide 以 水 为溶剂， 生成 (2S)-5-[[(2R)-3-[1-[2-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-oxoethyl]-2,5-dioxopyrrolidin-3-yl]sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-2-amino-5-oxopentanoic acid
  参考文献：
  名称：

  Chemoselective ligation of maleimidosugars to peptides/protein for the preparation of neoglycopeptides/neoglycoprotein

  摘要：

  Two types of maleimidosugars as thiol-selective carbohydrates, 1-maleimidosugars and acetyl-linked maleimidosugars, were efficiently synthesized. They were coupled to glutathione, Fas peptide and bovine serium albumin (BSA) to prepare the corresponding glycosylated peptides and a protein via stable thioether linkages in a chemoselective manner. (C) 2001 Elsevier Science Ltd. All lights reserved.

  DOI：

  10.1016/s0040-4039(00)02286-3
• 作为产物：
  描述：

  D-GlcNAc 在 碳酸氢铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 N-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,5-dioxopyrrol-1-yl)acetamide
  参考文献：
  名称：

  Chemoselective ligation of maleimidosugars to peptides/protein for the preparation of neoglycopeptides/neoglycoprotein

  摘要：

  Two types of maleimidosugars as thiol-selective carbohydrates, 1-maleimidosugars and acetyl-linked maleimidosugars, were efficiently synthesized. They were coupled to glutathione, Fas peptide and bovine serium albumin (BSA) to prepare the corresponding glycosylated peptides and a protein via stable thioether linkages in a chemoselective manner. (C) 2001 Elsevier Science Ltd. All lights reserved.

  DOI：

  10.1016/s0040-4039(00)02286-3