benzyl <<4(S)-methyl-3(S)-<5-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-D-phenylglycyl>amino>-2-oxo-1-azetidinyl>oxy>acetate | 131080-82-5

• 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: benzyl <<4(S)-methyl-3(S)-<5-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-D-phenylglycyl>amino>-2-oxo-1-azetidinyl>oxy>acetate
• 英文别名: benzyl [(4(S)-methyl-3(S)-{[N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-D-phenylglycyl]amino}-2-oxo-1-azetidinyl)oxy]acetate
• CAS: 131080-82-5
• 化学式: C₇₁H₈₃N₉O₁₆
• 分子量: 1318.49
• InChiKey: OSYFBPDGTSTXIY-KGAHPFOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  96.0
• 可旋转键数：
  38.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  299.19
• 氢给体数：
  5.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  benzyl <<4(S)-methyl-3(S)-<5-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-D-phenylglycyl>amino>-2-oxo-1-azetidinyl>oxy>acetate 在 palladium on activated charcoal 氢气 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 以95%的产率得到<<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：

  benzyl 2-[(2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl]oxyacetate 在 potassium hydrogencarbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 2.5h， 生成 benzyl <<4(S)-methyl-3(S)-<5-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-D-phenylglycyl>amino>-2-oxo-1-azetidinyl>oxy>acetate
  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