| 804557-90-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• CAS: 804557-90-2
• 化学式: C₆₂H₈₃N₁₃O₁₃
• 分子量: 1218.42
• InChiKey: RDRTWVGQMIPJHV-CSSFAGKYSA-N

物化性质

• 沸点：
  1611.5±65.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.61
• 重原子数：
  88.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  414.64
• 氢给体数：
  13.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Nonanoic acid [(2R,3R,4R,5S,6R)-2-(2-azido-ethoxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-amide 、 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N-[(2R,3R,4R,5S,6R)-2-[2-[4-[[(3R,6S,9S,12S,15S,18S,21S,24R,27S,30S)-21-(2-amino-2-oxoethyl)-18-(3-amino-3-oxopropyl)-9-(3-aminopropyl)-3,27-dibenzyl-15-[(4-hydroxyphenyl)methyl]-6-(2-methylpropyl)-2,5,8,11,14,17,20,23,26,29-decaoxo-12-propan-2-yl-1,4,7,10,13,16,19,22,25,28-decazabicyclo[28.3.0]tritriacontan-24-yl]methyl]triazol-1-yl]ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]nonanamide
  参考文献：
  名称：

  A Chemoenzymatic Approach to Glycopeptide Antibiotics

  摘要：

  Many biologically active natural products are constrained by macrocyclization and modified with carbohydrates. These two types of modifications are essential for their biological activities. Here we report a chemoenzymatic approach to make carbohydrate-modified cyclic peptide antibiotics. Using a thioesterase domain from the decapeptide tyrocidine synthetase, 13 head-to-tail cyclized tyrocidine derivatives were obtained with one to three propargylglycines incorporated at positions 3-8. These cyclic peptides were then conjugated to 21 azido sugars via copper(I)-catalyzed cycloaddition. Antibacterial and hemolytic assays showed that the two best glycopeptides, Tyc4PG-14 and Tyc4PG-15, have a 6-fold better therapeutic index than the natural tyrocidine. We believe this method will also be useful for modifying other natural products to search for new therapeutics.

  DOI：

  10.1021/ja045147v
• 作为产物：
  描述：

  在 tyrocidine synthetase thioesterase domain 作用下， 以 various solvent(s) 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  A Chemoenzymatic Approach to Glycopeptide Antibiotics

  摘要：

  Many biologically active natural products are constrained by macrocyclization and modified with carbohydrates. These two types of modifications are essential for their biological activities. Here we report a chemoenzymatic approach to make carbohydrate-modified cyclic peptide antibiotics. Using a thioesterase domain from the decapeptide tyrocidine synthetase, 13 head-to-tail cyclized tyrocidine derivatives were obtained with one to three propargylglycines incorporated at positions 3-8. These cyclic peptides were then conjugated to 21 azido sugars via copper(I)-catalyzed cycloaddition. Antibacterial and hemolytic assays showed that the two best glycopeptides, Tyc4PG-14 and Tyc4PG-15, have a 6-fold better therapeutic index than the natural tyrocidine. We believe this method will also be useful for modifying other natural products to search for new therapeutics.

  DOI：

  10.1021/ja045147v