N²-<(N²,N^im-di-tert-butyoxycarbonyl)-(S)-histydyl-(S)-norvalyl>, N³-(S)-2-bromosuccinamoyl,(S)-2,3-diaminopropanoic acid

• 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: N²-<(N²,N^im-di-tert-butyoxycarbonyl)-(S)-histydyl-(S)-norvalyl>, N³-(S)-2-bromosuccinamoyl,(S)-2,3-diaminopropanoic acid
• 英文别名: N²-[(N²,N^im-di-tert-butyoxycarbonyl)-(S)-histydyl-(S)-norvalyl], N³-(S)-2-bromosuccinamoyl,(S)-2,3-diaminopropanoic acid；(2S)-3-[[(2S)-4-amino-2-bromo-4-oxobutanoyl]amino]-2-[[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]imidazol-4-yl]propanoyl]amino]pentanoyl]amino]propanoic acid
• 化学式: C₂₈H₄₄BrN₇O₁₀
• 分子量: 718.602
• InChiKey: NOUUFKYRZNFFGP-VJANTYMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  250
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N²-<(N²,N^im-di-tert-butyoxycarbonyl)-(S)-histydyl-(S)-norvalyl>, N³-(S)-2-bromosuccinamoyl,(S)-2,3-diaminopropanoic acid 、 三氟乙酸 在 苯甲醚 作用下， 反应 2.0h， 以96%的产率得到(S)-2-{(S)-2-[(S)-2-Amino-3-(1H-imidazol-4-yl)-propionylamino]-pentanoylamino}-3-((S)-2-bromo-3-carbamoyl-propionylamino)-propionic acid; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Synthesis and biological activities of peptides containing N3-(S)-2-bromosuccinamoyl-(S)-2,3-diaminopropanoic acid

  摘要：

  A series of peptides with N-3-(S)-bromosuccinamoyl-(S)-2,3-diaminopropanoic acid, a novel selective inhibitor of glucosamine-6-phosphate synthase were synthesized and evaluated in vitro for antimicrobial activity against selected bacterial and fungal strains including dermatophytes. All the peptides were found to be active against a broad range of bacteria and fungi. Tripeptides exhibited remarkable anticandidal activity.

  DOI：

  10.1016/0223-5234(94)90127-9
• 作为产物：
  描述：

  N²-(S)-norvalyl, N³-(S)-2-bromosuccinamoyl,(S)-2,3-diaminopropanoic acid trifluoroacetate salt 、 2,5-二氧代-1-吡咯烷基N,1-二{[(2-甲基-2-丙基)氧基]羰基}-L-组氨酸酯 在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 以70%的产率得到N²-<(N²,N^im-di-tert-butyoxycarbonyl)-(S)-histydyl-(S)-norvalyl>, N³-(S)-2-bromosuccinamoyl,(S)-2,3-diaminopropanoic acid
  参考文献：
  名称：

  Synthesis and biological activities of peptides containing N3-(S)-2-bromosuccinamoyl-(S)-2,3-diaminopropanoic acid

  摘要：

  A series of peptides with N-3-(S)-bromosuccinamoyl-(S)-2,3-diaminopropanoic acid, a novel selective inhibitor of glucosamine-6-phosphate synthase were synthesized and evaluated in vitro for antimicrobial activity against selected bacterial and fungal strains including dermatophytes. All the peptides were found to be active against a broad range of bacteria and fungi. Tripeptides exhibited remarkable anticandidal activity.

  DOI：

  10.1016/0223-5234(94)90127-9

文献信息

• Synthesis and biological activities of peptides containing N3-(S)-2-bromosuccinamoyl-(S)-2,3-diaminopropanoic acid
  作者：R Andruszkiewicz、H Chmara、T Zieniawa、E Borowski

  DOI：10.1016/0223-5234(94)90127-9

  日期：1994.1

  A series of peptides with N-3-(S)-bromosuccinamoyl-(S)-2,3-diaminopropanoic acid, a novel selective inhibitor of glucosamine-6-phosphate synthase were synthesized and evaluated in vitro for antimicrobial activity against selected bacterial and fungal strains including dermatophytes. All the peptides were found to be active against a broad range of bacteria and fungi. Tripeptides exhibited remarkable anticandidal activity.