N-[(2R,3R,4R,5S,6R)-2-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide | 333384-28-4

• 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)-2-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-(2,5-dioxopyrrol-1-yl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 333384-28-4
• 化学式: C₁₂H₁₆N₂O₇
• 分子量: 300.268
• InChiKey: VXSDLFUIONPTFK-NJOIIQIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(2R,3R,4R,5S,6R)-2-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide 、 Ac-VARLSCKSVNAQ-NH2 以 水 、 二甲基亚砜 为溶剂， 生成 (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2R)-3-[1-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,5-dioxopyrrolidin-3-yl]sulfanyl-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-methylbutanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]propanoyl]amino]-6-aminohexanoyl]amino]-3-hydroxypropanoyl]amino]-3-methylbutanoyl]amino]-4-amino-4-oxobutanoyl]amino]propanoyl]amino]pentanediamide
  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：

  2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖酰基叠氮化物 在 palladium on activated charcoal 4-二甲氨基吡啶 、 水 、 氢气 、 sodium methylate 、 六甲基二硅氮烷 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 N-[(2R,3R,4R,5S,6R)-2-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-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