(N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl)-(N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine | 124620-56-0

• 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
• 英文别名: (2S)-5-[acetyl(phenylmethoxy)amino]-2-[[(2S)-5-[acetyl(phenylmethoxy)amino]-2-[[(2S)-5-[acetyl(phenylmethoxy)amino]-2-(phenylmethoxycarbonylamino)pentanoyl]amino]pentanoyl]amino]pentanoic acid
• CAS: 124620-56-0
• 化学式: C₅₀H₆₂N₆O₁₂
• 分子量: 939.075
• InChiKey: UODWLBMSAMIYKW-LCALOIESSA-N

物化性质

• 熔点：
  118-119 °C
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  68
• 可旋转键数：
  30
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  222
• 氢给体数：
  4
• 氢受体数：
  12

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 在 palladium on activated charcoal 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-4-hydroxyphenylglycine
  参考文献：
  名称：

  Synthesis and siderophore activity of albomycin-like peptides derived from N5-acetyl-N5-hydroxy-L-ornithine

  摘要：

  N5-Acetyl-N5-hydroxy-L-ornithine (1), the key constituent of several microbial siderophores, has been synthesized in 23 % yield overall from N-Cbz-L-glutamic acid 1-tert-butyl ester (6) derived from L-glutamic acid. Reduction of 6 to 7 and treatment with N-[(trichloroethoxy)carbonyl]-O-benzylhydroxylamine (8), and diethyl azodicarboxylate and triphenylphosphine followed by deprotection produced the protected N5-acetyl-N5-hydroxy-L-ornithine derivatives 11 and 12 in large quantities (10-20 g). Following alpha-amino and alpha-carboxyl deprotections of 11 and 12, EEDQ [2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline] mediated peptide coupling and final deprotection provided amino acid 1 and six albomycin-like peptides (20, 23, 25, 28, 35, and 36). The growth-promoting ability of each was evaluated with the siderophore biosynthesis mutant Shigella flexneri SA240 (SA 100 iucD:Tn5). These results indicate that substantial modification of the framework of peptide-based siderophores can be tolerated by microbial iron-transport systems.

  DOI：

  10.1021/jm00107a013
• 作为产物：
  描述：

  Allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate 在 四(三苯基膦)钯 、 O-苄基羟胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以74%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
  参考文献：
  名称：

  Synthesis and siderophore activity of albomycin-like peptides derived from N5-acetyl-N5-hydroxy-L-ornithine

  摘要：

  N5-Acetyl-N5-hydroxy-L-ornithine (1), the key constituent of several microbial siderophores, has been synthesized in 23 % yield overall from N-Cbz-L-glutamic acid 1-tert-butyl ester (6) derived from L-glutamic acid. Reduction of 6 to 7 and treatment with N-[(trichloroethoxy)carbonyl]-O-benzylhydroxylamine (8), and diethyl azodicarboxylate and triphenylphosphine followed by deprotection produced the protected N5-acetyl-N5-hydroxy-L-ornithine derivatives 11 and 12 in large quantities (10-20 g). Following alpha-amino and alpha-carboxyl deprotections of 11 and 12, EEDQ [2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline] mediated peptide coupling and final deprotection provided amino acid 1 and six albomycin-like peptides (20, 23, 25, 28, 35, and 36). The growth-promoting ability of each was evaluated with the siderophore biosynthesis mutant Shigella flexneri SA240 (SA 100 iucD:Tn5). These results indicate that substantial modification of the framework of peptide-based siderophores can be tolerated by microbial iron-transport systems.

  DOI：

  10.1021/jm00107a013

文献信息

• Synthesis and Biological Evaluation of a Carbocyclic Azanoraristeromycin Siderophore Conjugate
  作者：Arun Ghosh、Marvin J. Miller、Erik De Clercq、Jan Balzarini

  DOI：10.1080/15257779908043069

  日期：1999.2

  Synthesis and biological evaluation of a carbocyclic azanoraristeromycin siderophore conjugate 22 is reported. Coupling of previously prepared L-alanyl-4'-azanoraristeromycin 19 with protected tripeptide trihydroxamate 20, followed by hydrogenolytic removal of all protecting groups, provided the first carbocylic azanoraristeromycin siderophore conjugate (22, 8 with iron). Compounds 19 and 22 showed

  报道了碳环的阿扎诺拉霉素霉素铁载体缀合物22的合成和生物学评估。预先制备的L-丙氨酰基-4'-氮杂多菌霉素19与受保护的三肽三氢肟酸酯20偶联，然后氢解除去所有保护基团，从而提供了第一个碳环的氮杂阿那霉素铁载体（22、8，含铁）。化合物19和22显示出对肿瘤细胞的抑制活性，尤其是缀合物22显示出对已知被S-腺苷同型半胱氨酸水解酶抑制剂抑制的那些病毒（即reo，副流感，牛痘，巨细胞巨细胞）的显着活性。
• N5-Acetyl-N5-hydroxy-L-ornithine-derived siderophore-carbacephalosporin .beta.-lactam conjugates: iron transport mediated drug delivery
  作者：E. Kurt Dolence、Albert A. Minnick、Marvin J. Miller

  DOI：10.1021/jm00164a001

  日期：1990.2
• Synthesis and siderophore and antibacterial activity of N5-acetyl-N5-hydroxyl-L-ornithine derived siderophore-.beta.-lactam conjugates: iron transport mediated drug delivery
  作者：E. Kurt Dolence、Albert A. Minnick、Chia En Lin、Marvin J. Miller、Shelley M. Payne

  DOI：10.1021/jm00107a014

  日期：1991.3

  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.
• DOLENCE, E. KURT.;LIN, CHIA-EN;MILLER, MARVIN J.;PAYNE, SHELLEY M., J. MED. CHEM., 34,(1991) N, C. 956-968
  作者：DOLENCE, E. KURT.、LIN, CHIA-EN、MILLER, MARVIN J.、PAYNE, SHELLEY M.

  DOI：——

  日期：——