carboxyeremomycin AA3,AA7-bis[N-(p-fluorobenzyl)amide] | 1163740-02-0

• 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
• 英文名称: carboxyeremomycin AA3,AA7-bis[N-(p-fluorobenzyl)amide]
• CAS: 1163740-02-0
• 化学式: C₈₇H₁₀₀ClF₂N₁₁O₂₅
• 分子量: 1773.26
• InChiKey: XMTHDDSVTQGKEX-ZSPBFEOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  126.0
• 可旋转键数：
  19.0
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  552.78
• 氢给体数：
  20.0
• 氢受体数：
  28.0

反应信息

• 作为产物：
  描述：

  4-氟苄胺盐酸盐 、 carboxyeremomycin 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 生成 carboxyeremomycin AA3,AA7-bis[N-(p-fluorobenzyl)amide]
  参考文献：
  名称：

  New derivatives of eremomycin containing 15N or F atoms for NMR study

  摘要：

  New semisynthetic derivatives of eremomycin containing N-15 or F atoms were obtained for studying the antibiotic-target interaction in intact cells of Gram-positive bacteria by REDOR NMR method. Interaction of the terminal carboxyl group of amino acid 7 (AA7) of eremomycin with amines in the presence of PyBOP and TBTU reagents resulted in the corresponding [N-15]-amide, p-fluorobenzylamide, p-fluorophenylpiperazide, and 6-N-(p-fluorobenzyl)aminohexylamide. A selective method of [N-15]-amidation of carboxyl group of amino acid 3 (AA3) of carboxyeremomycin was developed, and the amide of eremomycin containing [N-15] in AA3 amide group near the antibiotic binding pocket was obtained. Carboxyeremomycin bisamides substituted at AA3 and AA7 and containing two atoms of [N-15] or F were obtained from carboxyeremomycin and [N-15]NH4Cl or the corresponding p-fluorobenzylamine hydrochloride in the presence of PyBOP at pH similar to 8. The Edman degradation of eremomycin p-fluorobenzylamide gave de-(D-MeLeu)-eremomycin p-fluorobenzylamide, a hexapeptide derivative incapable of the antibiotic binding with -D-Ala-D-Ala fragment of growing cell wall peptidoglycan. Among the compounds studied, carboxyeremomycin bis-p-fluorobenzylamide showed the best activity against both the glycopeptides-sensitive and glycopeptides-resistant strains of staphylococci and enterococci.

  DOI：

  10.1134/s1068162008060162