25-epi-24-O-benzyl-globomycin | 694528-07-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 25-epi-24-O-benzyl-globomycin
• CAS: 694528-07-9
• 化学式: C₃₉H₆₃N₅O₉
• 分子量: 745.957
• InChiKey: LNXKCFDGGKVFDS-BRGLTHKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  53.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  192.47
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  25-epi-24-O-benzyl-globomycin 在 palladium dihydroxide 氢气 作用下， 生成 25-epi-globomycin
  参考文献：
  名称：

  Synthesis and antimicrobial activity of novel globomycin analogues

  摘要：

  Globomycin, 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. One of the analogues showed a more potent activity against Gram-negative bacteria than globomycin and also exhibited antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00432-3
• 作为产物：
  描述：

  N-((2R,3R)-3-hydroxy-2-methylnonanoyl)-N-Me-L-Leu-L-Ile-L-Ser(Bn)-OAllyl 在 吗啉 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 碳酸二异丙酯 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 生成 25-epi-24-O-benzyl-globomycin
  参考文献：
  名称：

  Synthesis and antimicrobial activity of novel globomycin analogues

  摘要：

  Globomycin, 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. One of the analogues showed a more potent activity against Gram-negative bacteria than globomycin and also exhibited antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00432-3

文献信息

• Structure–activity relationships of globomycin analogues as antibiotics
  作者：Toshihiro Kiho、Mizuka Nakayama、Kayo Yasuda、Shunichi Miyakoshi、Masatoshi Inukai、Hiroshi Kogen

  DOI：10.1016/j.bmc.2003.10.055

  日期：2004.1

  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.