2-Hydroxy-N-{5-[hydroxy-((E)-oct-2-enoyl)-amino]-pentyl}-2-({5-[hydroxy-((E)-oct-2-enoyl)-amino]-pentylcarbamoyl}-methyl)-succinamic acid | 777939-32-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Hydroxy-N-{5-[hydroxy-((E)-oct-2-enoyl)-amino]-pentyl}-2-({5-[hydroxy-((E)-oct-2-enoyl)-amino]-pentylcarbamoyl}-methyl)-succinamic acid
• 英文别名: 2-hydroxy-4-[5-[hydroxy-[(E)-oct-2-enoyl]amino]pentylamino]-2-[2-[5-[hydroxy-[(E)-oct-2-enoyl]amino]pentylamino]-2-oxoethyl]-4-oxobutanoic acid
• CAS: 777939-32-9
• 化学式: C₃₂H₅₆N₄O₉
• 分子量: 640.818
• InChiKey: OXMVUVWFSVVCJU-IWGRKNQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  45
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  197
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-N-{5-[hydroxy-((E)-oct-2-enoyl)-amino]-pentyl}-2-({5-[hydroxy-((E)-oct-2-enoyl)-amino]-pentylcarbamoyl}-methyl)-succinamic acid 在 三氟乙酸 作用下， 反应 3.0h， 以0.046 g的产率得到(E)-Oct-2-enoic acid hydroxy-{5-[3-hydroxy-3-({5-[hydroxy-((E)-oct-2-enoyl)-amino]-pentylcarbamoyl}-methyl)-2,5-dioxo-pyrrolidin-1-yl]-pentyl}-amide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Acinetoferrin Homologues for Use as Iron Transport Probes in Mycobacteria

  摘要：

  Four new acinetoferrin homologues were synthesized using a modular synthetic approach. Two linear and two cyclic imide derivatives were generated and evaluated for growth stimulating behavior in Mycobacterium avium subsp paratuberculosis. The yield for the tandem coupling of a functionalized aminohydroxamic acid motif (2 equiv) to a tert-butyl citrate derivative was significantly improved using DCC and N-hydroxysuccinimide. H-1 NMR spectroscopy (CD3OD) provided a convenient method for monitoring the final imidization step in TFA using the doublet patterns between 2.5 and 3.06 ppm. New protocols demonstrated that only a 20% growth enhancement was observed with M. avium subsp. paratuberculosis using the imide of acinetoferrin. Last, a siderophore from Streptomyces pilosus, deferrioxamine B, was shown to cross-feed M. avium subsp. paratuberculosis with the same efficiency as the more costly, native chelator, mycobactin J.

  DOI：

  10.1021/jm049805y
• 作为产物：
  描述：

  枸橼酸叔-丁酯 在 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-Hydroxy-N-{5-[hydroxy-((E)-oct-2-enoyl)-amino]-pentyl}-2-({5-[hydroxy-((E)-oct-2-enoyl)-amino]-pentylcarbamoyl}-methyl)-succinamic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Acinetoferrin Homologues for Use as Iron Transport Probes in Mycobacteria

  摘要：

  Four new acinetoferrin homologues were synthesized using a modular synthetic approach. Two linear and two cyclic imide derivatives were generated and evaluated for growth stimulating behavior in Mycobacterium avium subsp paratuberculosis. The yield for the tandem coupling of a functionalized aminohydroxamic acid motif (2 equiv) to a tert-butyl citrate derivative was significantly improved using DCC and N-hydroxysuccinimide. H-1 NMR spectroscopy (CD3OD) provided a convenient method for monitoring the final imidization step in TFA using the doublet patterns between 2.5 and 3.06 ppm. New protocols demonstrated that only a 20% growth enhancement was observed with M. avium subsp. paratuberculosis using the imide of acinetoferrin. Last, a siderophore from Streptomyces pilosus, deferrioxamine B, was shown to cross-feed M. avium subsp. paratuberculosis with the same efficiency as the more costly, native chelator, mycobactin J.

  DOI：

  10.1021/jm049805y

文献信息

• Synthesis and Biological Evaluation of New Acinetoferrin Homologues for Use as Iron Transport Probes in Mycobacteria
  作者：Richard A. Gardner、George Ghobrial、Saleh A. Naser、Phanstiel

  DOI：10.1021/jm049805y

  日期：2004.9.1

  Four new acinetoferrin homologues were synthesized using a modular synthetic approach. Two linear and two cyclic imide derivatives were generated and evaluated for growth stimulating behavior in Mycobacterium avium subsp paratuberculosis. The yield for the tandem coupling of a functionalized aminohydroxamic acid motif (2 equiv) to a tert-butyl citrate derivative was significantly improved using DCC and N-hydroxysuccinimide. H-1 NMR spectroscopy (CD3OD) provided a convenient method for monitoring the final imidization step in TFA using the doublet patterns between 2.5 and 3.06 ppm. New protocols demonstrated that only a 20% growth enhancement was observed with M. avium subsp. paratuberculosis using the imide of acinetoferrin. Last, a siderophore from Streptomyces pilosus, deferrioxamine B, was shown to cross-feed M. avium subsp. paratuberculosis with the same efficiency as the more costly, native chelator, mycobactin J.