L-Leu-L-allo-Ile-L-Ser(Bn)-OAllyl | 656256-27-8

• 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: L-Leu-L-allo-Ile-L-Ser(Bn)-OAllyl
• CAS: 656256-27-8
• 化学式: C₂₅H₃₉N₃O₅
• 分子量: 461.602
• InChiKey: ZCTNZOAIQIYPOH-GBAJDQEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  33.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  119.75
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  L-Leu-L-allo-Ile-L-Ser(Bn)-OAllyl 在 四(三苯基膦)钯 吗啉 、 4-二甲氨基吡啶 、 氰基磷酸二乙酯 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 溶剂黄146 、 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 为溶剂， 反应 36.0h， 生成 (S)-2-[(2S,3R)-2-((S)-2-{(2R,3R)-3-[2-((2S,3S)-2-Amino-3-hydroxy-butyrylamino)-acetoxy]-2-methyl-nonanoylamino}-4-methyl-pentanoylamino)-3-methyl-pentanoylamino]-3-benzyloxy-propionic acid; compound with trifluoro-acetic acid
  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-((S)-2-tert-butoxycarbonylamino-4-methyl-pentanoylamino)-3-methyl-pentanoylamino]-propionic acid allyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 以98%的产率得到L-Leu-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

文献信息

• Synthesis and antimicrobial activity of novel globomycin analogues
  作者：Toshihiro Kiho、Mizuka Nakayama、Kayo Yasuda、Shunichi Miyakoshi、Masatoshi Inukai、Hiroshi Kogen

  DOI：10.1016/s0960-894x(03)00432-3

  日期：2003.7

  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.