(2-{[5-(4-{2-[bis(2-{[2-(1-thio-β-D-galactopyranosyl)ethanoyl]amino}ethyl)amino]ethylcarbamoyl}propylsulfanyl)ethanoyl]amino}ethyl)(2-{[2-(1-thio-β-D-galactopyranosyl)ethanoyl]amino}ethyl)(2-tert-butoxycarbonylaminoethyl)amine | 690632-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-{[5-(4-{2-[bis(2-{[2-(1-thio-β-D-galactopyranosyl)ethanoyl]amino}ethyl)amino]ethylcarbamoyl}propylsulfanyl)ethanoyl]amino}ethyl)(2-{[2-(1-thio-β-D-galactopyranosyl)ethanoyl]amino}ethyl)(2-tert-butoxycarbonylaminoethyl)amine
• CAS: 690632-57-6
• 化学式: C₄₇H₈₆N₈O₂₂S₄
• 分子量: 1243.5
• InChiKey: SHSPDHDDIGBUBV-IIUWTYDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.19
• 重原子数：
  81.0
• 可旋转键数：
  36.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  460.76
• 氢给体数：
  18.0
• 氢受体数：
  28.0

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 (2-{[5-(4-{2-[bis(2-{[2-(1-thio-β-D-galactopyranosyl)ethanoyl]amino}ethyl)amino]ethylcarbamoyl}propylsulfanyl)ethanoyl]amino}ethyl)(2-{[2-(1-thio-β-D-galactopyranosyl)ethanoyl]amino}ethyl)(2-tert-butoxycarbonylaminoethyl)amine 以 二氯甲烷 为溶剂， 反应 2.0h， 以94%的产率得到
  参考文献：
  名称：

  Glycodendriproteins:  A Synthetic Glycoprotein Mimic Enzyme with Branched Sugar-Display Potently Inhibits Bacterial Aggregation

  摘要：

  The continuing ability of bacteria to resist current antibiotic treatments highlights the need for alternative strategies for inhibiting their pathogenicity. Bacterial attachment is a major factor in infectivity and virulence. This key binding phase of bacteria to any potential host is mediated by adhesin proteins and so these present an attractive therapeutic target for antiinfective blocking strategies. However, the natural ligands to adhesins are large, typically complex molecules that are difficult to mimic with small molecules. We describe here a method that creates precise synthetic mimics of glycoproteins that are designed to bind adhesins. By using protein-degrading enzymes as the basis for these mimics we have created large-molecule protein ligands that inhibit aggregation of pathogenic bacteria at levels greater than a million-fold higher than small-molecule inhibitors of adhesins.

  DOI：

  10.1021/ja031698u
• 作为产物：
  描述：

  bis-{N-[2-(1-thio-β-D-galactopyranosyl)ethanoyl]aminoethyl}-{N-tert-butylcarbamoylaminoethyl}amine 在 碳酸氢钠 、 三氟乙酸 、 1,4-二巯基-2,3-丁二醇 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2-{[5-(4-{2-[bis(2-{[2-(1-thio-β-D-galactopyranosyl)ethanoyl]amino}ethyl)amino]ethylcarbamoyl}propylsulfanyl)ethanoyl]amino}ethyl)(2-{[2-(1-thio-β-D-galactopyranosyl)ethanoyl]amino}ethyl)(2-tert-butoxycarbonylaminoethyl)amine
  参考文献：
  名称：

  Glycodendriproteins:  A Synthetic Glycoprotein Mimic Enzyme with Branched Sugar-Display Potently Inhibits Bacterial Aggregation

  摘要：

  The continuing ability of bacteria to resist current antibiotic treatments highlights the need for alternative strategies for inhibiting their pathogenicity. Bacterial attachment is a major factor in infectivity and virulence. This key binding phase of bacteria to any potential host is mediated by adhesin proteins and so these present an attractive therapeutic target for antiinfective blocking strategies. However, the natural ligands to adhesins are large, typically complex molecules that are difficult to mimic with small molecules. We describe here a method that creates precise synthetic mimics of glycoproteins that are designed to bind adhesins. By using protein-degrading enzymes as the basis for these mimics we have created large-molecule protein ligands that inhibit aggregation of pathogenic bacteria at levels greater than a million-fold higher than small-molecule inhibitors of adhesins.

  DOI：

  10.1021/ja031698u