N-((2R,3R)-3-[Boc-L-allo-Thr(TBS)-GlyO]-2-methylnonanoyl)-L-homo-Pro-L-allo-Ile-L-Ser(Bn)-OAllyl | 694528-01-3

• 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: N-((2R,3R)-3-[Boc-L-allo-Thr(TBS)-GlyO]-2-methylnonanoyl)-L-homo-Pro-L-allo-Ile-L-Ser(Bn)-OAllyl
• CAS: 694528-01-3
• 化学式: C₅₂H₈₇N₅O₁₂Si
• 分子量: 1002.37
• InChiKey: OHGIZBZTCMWORX-CPFNOSEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.27
• 重原子数：
  70.0
• 可旋转键数：
  28.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  217.0
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N-((2R,3R)-3-[Boc-L-allo-Thr(TBS)-GlyO]-2-methylnonanoyl)-L-homo-Pro-L-allo-Ile-L-Ser(Bn)-OAllyl 在 palladium dihydroxide 、 四(三苯基膦)钯 吗啉 、 四丁基氟化铵 、 氢气 、 溶剂黄146 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 78.0h， 生成 (6R,7R,13S,16S,19S,21aS)-19-((R)-sec-Butyl)-7-hexyl-13-((S)-1-hydroxy-ethyl)-16-hydroxymethyl-6-methyl-tetradecahydro-8-oxa-4a,11,14,17,20-pentaaza-benzocyclononadecene-5,9,12,15,18,21-hexaone
  参考文献：
  名称：

  Structure–activity relationships of globomycin analogues as antibiotics

  摘要：

  Globomycin (1a), a signal peptidase II inhibitor, and its derivatives show potent antibacterial activity against Gram-negative bacteria. The synthesis and antimicrobial activity of novel globomycin analogues are reported. The hydroxyl group in the L-Ser residue was essential for the antimicrobial activity and the length of the alkyl side chain greatly influenced the activity. In addition, derivatives that had a modified cyclic core exhibited weak activity. One of the analogues showed a wider antimicrobial spectrum, effective against not only Gram-negative but also Gram-positive bacteria. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.055
• 作为产物：
  描述：

  (S)-3-Benzyloxy-2-((2S,3R)-2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-propionic acid allyl ester 在 盐酸 、 4-二甲氨基吡啶 、 氰基磷酸二乙酯 、 camphor-10-sulfonic acid 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 N-((2R,3R)-3-[Boc-L-allo-Thr(TBS)-GlyO]-2-methylnonanoyl)-L-homo-Pro-L-allo-Ile-L-Ser(Bn)-OAllyl
  参考文献：
  名称：

  Structure–activity relationships of globomycin analogues as antibiotics

  摘要：

  Globomycin (1a), a signal peptidase II inhibitor, and its derivatives show potent antibacterial activity against Gram-negative bacteria. The synthesis and antimicrobial activity of novel globomycin analogues are reported. The hydroxyl group in the L-Ser residue was essential for the antimicrobial activity and the length of the alkyl side chain greatly influenced the activity. In addition, derivatives that had a modified cyclic core exhibited weak activity. One of the analogues showed a wider antimicrobial spectrum, effective against not only Gram-negative but also Gram-positive bacteria. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.055