[(2R,3S,4R,5R)-3,4,6-triacetyloxy-5-[3-(3-methyldiazirin-3-yl)propanoylamino]oxan-2-yl]methyl acetate | 1015698-40-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R,5R)-3,4,6-triacetyloxy-5-[3-(3-methyldiazirin-3-yl)propanoylamino]oxan-2-yl]methyl acetate
• CAS: 1015698-40-4
• 化学式: C₁₉H₂₇N₃O₁₀
• 分子量: 457.437
• InChiKey: UZYLHDJBFVVKBM-XWEABGILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5R)-3,4,6-triacetyloxy-5-[3-(3-methyldiazirin-3-yl)propanoylamino]oxan-2-yl]methyl acetate 在 碳酸氢铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 以77%的产率得到
  参考文献：
  名称：

  Synthesis of Cell-Permeable N-Acetylhexosamine 1-Phosphates

  摘要：

  DOI：

  10.1021/acs.joc.1c01781
• 作为产物：
  描述：

  3-甲基-3H-双吖丙啶-3-丙酸 在 4-二甲氨基吡啶 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 [(2R,3S,4R,5R)-3,4,6-triacetyloxy-5-[3-(3-methyldiazirin-3-yl)propanoylamino]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  A Traceless Staudinger Reagent To Deliver Diazirines

  摘要：

  A triarylphosphine reagent that reacts with organic azides to install amide-linked diazirines is reported. This traceless Staudinger reagent reacts with complex organic azides to yield amide-linked diazirines, thus expanding the scope of the utility of both azide and diazirine chemistry.

  DOI：

  10.1021/ol402404n

文献信息

• Photoactivatable Crosslinking Sugars for Capturing Glycoprotein Interactions
  作者：Yoshihito Tanaka、Jennifer J. Kohler

  DOI：10.1021/ja7109772

  日期：2008.3.1

  Carbohydrates are key mediators of cell-cell, cell-virus, and cell-ligand interactions. These interactions are often difficult to study because they are characterized by fast off rates and low affinities. Photoactivatable crosslinking sugars can be used to capture these transient interactions by forming a covalent bond between the carbohydrate and its binding partner. We designed and synthesized 'photo-sugars' that contain diazirine moieties on the N-acyl side chains. We demonstrated that these photo-sugars could be metabolically incorporated onto the surface of living cells. Upon UV irradiation, specific crosslinks were formed between glycoprotein binding partners. Importantly, photo-sugar incorporation competes efficiently with endogenous carbohydrate biosynthesis and is compatible with the sialic acid modifications, such as 9-O-acetylation, that regulate binding events.