tert-butyl 2-hydroxy-4-[6-[hydroxy-[(E)-oct-2-enoyl]amino]hexylamino]-2-[2-[6-[hydroxy-[(E)-oct-2-enoyl]amino]hexylamino]-2-oxoethyl]-4-oxobutanoate | 777939-45-4

• 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: tert-butyl 2-hydroxy-4-[6-[hydroxy-[(E)-oct-2-enoyl]amino]hexylamino]-2-[2-[6-[hydroxy-[(E)-oct-2-enoyl]amino]hexylamino]-2-oxoethyl]-4-oxobutanoate
• CAS: 777939-45-4
• 化学式: C₃₈H₆₈N₄O₉
• 分子量: 724.979
• InChiKey: RBTCBRVCFAFLLI-SIHVKLMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  51
• 可旋转键数：
  31
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  186
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-hydroxy-4-[6-[hydroxy-[(E)-oct-2-enoyl]amino]hexylamino]-2-[2-[6-[hydroxy-[(E)-oct-2-enoyl]amino]hexylamino]-2-oxoethyl]-4-oxobutanoate 在 三氟乙酸 作用下， 反应 6.0h， 生成 (E)-N-hydroxy-N-[6-[[2-[3-hydroxy-1-[6-[hydroxy-[(E)-oct-2-enoyl]amino]hexyl]-2,5-dioxopyrrolidin-3-yl]acetyl]amino]hexyl]oct-2-enamide
  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 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 tert-butyl 2-hydroxy-4-[6-[hydroxy-[(E)-oct-2-enoyl]amino]hexylamino]-2-[2-[6-[hydroxy-[(E)-oct-2-enoyl]amino]hexylamino]-2-oxoethyl]-4-oxobutanoate
  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.