N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine succinimido ester | 131080-79-0

• 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: N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine succinimido ester
• 英文别名: (2,5-dioxopyrrolidin-1-yl) (2S)-5-[acetyl(phenylmethoxy)amino]-2-[[(2S)-5-[acetyl(phenylmethoxy)amino]-2-[[(2S)-5-[acetyl(phenylmethoxy)amino]-2-(phenylmethoxycarbonylamino)pentanoyl]amino]pentanoyl]amino]pentanoate
• CAS: 131080-79-0
• 化学式: C₅₄H₆₅N₇O₁₄
• 分子量: 1036.15
• InChiKey: VENPWNFTPDGJHP-QQVWZEJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  75.0
• 可旋转键数：
  30.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  248.83
• 氢给体数：
  3.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine succinimido ester 在 palladium on activated charcoal 氢气 、 potassium hydrogencarbonate 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 <<4(S)-methyl-3(S)-<(N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-phenylglycyl)amino>-2-oxo-1-azetidinyl>oxy>acetic acid
  参考文献：
  名称：

  Synthesis and siderophore and antibacterial activity of N5-acetyl-N5-hydroxyl-L-ornithine derived siderophore-.beta.-lactam conjugates: iron transport mediated drug delivery

  摘要：

  N5-Acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithine, the functionally instrumental component of the albomycins and ferrichromes, has been incorporated as a ''carrier'' substructure into both carbacephalosporin and oxamazin type beta-lactam antibiotics. The previously synthesized protected version of this tripeptide (14) was coupled with various beta-lactam analogues 17, 19, 24, and 25 to give protected conjugates 21, 22, 26, and 27. Final deprotection by hydrogenolysis provided the deprotected siderophore-beta-lactam antibiotic conjugates 1-4. The growth-promoting ability of each has been evaluated using either the siderophore-deficient mutant Shigella flexneri SA 100 or S. flexneri SA240 (SA 100 iucD:Tn5). Measurement of the growth-promoting activity using two isogenic Escherichia coli strains differing only in the presence or absence of fhuA (hydroxamate ferrichrome receptor) suggests uptake by the hydroxamate iron-transport system. The antibacterial activity of these conjugates has been investigated, and the potential for use of the ferrichrome iron-transport system as a means of drug delivery is discussed.

  DOI：

  10.1021/jm00107a014
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 (N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl)-(N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine succinimido ester
  参考文献：
  名称：

  Synthesis and siderophore and antibacterial activity of N5-acetyl-N5-hydroxyl-L-ornithine derived siderophore-.beta.-lactam conjugates: iron transport mediated drug delivery

  摘要：

  N5-Acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithine, the functionally instrumental component of the albomycins and ferrichromes, has been incorporated as a ''carrier'' substructure into both carbacephalosporin and oxamazin type beta-lactam antibiotics. The previously synthesized protected version of this tripeptide (14) was coupled with various beta-lactam analogues 17, 19, 24, and 25 to give protected conjugates 21, 22, 26, and 27. Final deprotection by hydrogenolysis provided the deprotected siderophore-beta-lactam antibiotic conjugates 1-4. The growth-promoting ability of each has been evaluated using either the siderophore-deficient mutant Shigella flexneri SA 100 or S. flexneri SA240 (SA 100 iucD:Tn5). Measurement of the growth-promoting activity using two isogenic Escherichia coli strains differing only in the presence or absence of fhuA (hydroxamate ferrichrome receptor) suggests uptake by the hydroxamate iron-transport system. The antibacterial activity of these conjugates has been investigated, and the potential for use of the ferrichrome iron-transport system as a means of drug delivery is discussed.

  DOI：

  10.1021/jm00107a014