1,36-bis[2,3-bis(4-methoxybenzyloxy)benzoyl]-15,22-dioxo-18,19-dithia-1,5,9,14,23,28,32,36-octaaza-5,9,28,32-tetrakis[(N-tert-butoxycarbonyl)-L-threonyl]hexatriacontane | 1154500-45-4

• 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: 1,36-bis[2,3-bis(4-methoxybenzyloxy)benzoyl]-15,22-dioxo-18,19-dithia-1,5,9,14,23,28,32,36-octaaza-5,9,28,32-tetrakis[(N-tert-butoxycarbonyl)-L-threonyl]hexatriacontane
• 英文别名: tert-butyl N-[(2S,3R)-1-[3-[[2,3-bis[(4-methoxyphenyl)methoxy]benzoyl]amino]propyl-[3-[4-[3-[[3-[4-[3-[3-[[2,3-bis[(4-methoxyphenyl)methoxy]benzoyl]amino]propyl-[(2S,3R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]propyl-[(2S,3R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]butylamino]-3-oxopropyl]disulfanyl]propanoylamino]butyl-[(2S,3R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]propyl]amino]-3-hydroxy-1-oxobutan-2-yl]carbamate
• CAS: 1154500-45-4
• 化学式: C₁₀₈H₁₅₈N₁₂O₂₈S₂
• 分子量: 2136.64
• InChiKey: NDYMFEJHJPCVRF-WEPWIVHSSA-N

物化性质

• 沸点：
  1696.6±65.0 °C(predicted)
• 密度：
  1.216±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  150
• 可旋转键数：
  71
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  556
• 氢给体数：
  12
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  1,36-bis[2,3-bis(4-methoxybenzyloxy)benzoyl]-15,22-dioxo-18,19-dithia-1,5,9,14,23,28,32,36-octaaza-5,9,28,32-tetrakis[(N-tert-butoxycarbonyl)-L-threonyl]hexatriacontane 、 三氟乙酸 在 苯甲醚 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到1,36-bis(2,3-dihydroxybenzoyl)-15,22-dioxo-18,19-dithia-1,5,9,14,23,28,32,36-octaaza-5,9,28,32-tetrakis(L-threonyl)hexatriacontane tetrakis(trifluoroacetate)
  参考文献：
  名称：

  Vibriobactin Antibodies: A Vaccine Strategy

  摘要：

  A new target strategy in the development of bacterial vaccines, the induction of antibodies to microbial outer membrane ferrisiderophore complexes, is explored. A vibriobactin (VIB) analogue, with a thiol tether, -(2,3-dihydroxybenzoyl)-5,9-bis[[(4S,5R)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-4-oxazolyl]carbonyl]-14-(3-mercaptopropanoyl)-1,5,9,14-tetraazatetradecane, was synthesized and linked to ovalbumin (OVA) and bovine serum albumin (BSA). The antigenicity of the VIB microbial iron chelator conjugates and their iron complexes was evaluated. When mice were immunized with the resulting OVA-VIB conjugate, a selective and unequivocal antigenic response to the VIB hapten was observed; IgG monoclonal antibodies specific to the vibriobactin fragment of the BSA and OVA conjugates were isolated. The results are consistent with the idea that the isolated adducts of siderophores covalently linked to their bacterial outer membrane receptors represent a credible target for vaccine development.

  DOI：

  10.1021/jm900119q
• 作为产物：
  描述：

  3,3'-二氢氧啉酸 、 N4,N8-bis[(N-tert-butoxycarbonyl)-L-threonyl]-N1-[2,3-bis(4-methoxybenzyloxy)benzoyl]thermospermine 在 N,N'-羰基二咪唑 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以60%的产率得到1,36-bis[2,3-bis(4-methoxybenzyloxy)benzoyl]-15,22-dioxo-18,19-dithia-1,5,9,14,23,28,32,36-octaaza-5,9,28,32-tetrakis[(N-tert-butoxycarbonyl)-L-threonyl]hexatriacontane
  参考文献：
  名称：

  Vibriobactin Antibodies: A Vaccine Strategy

  摘要：

  A new target strategy in the development of bacterial vaccines, the induction of antibodies to microbial outer membrane ferrisiderophore complexes, is explored. A vibriobactin (VIB) analogue, with a thiol tether, -(2,3-dihydroxybenzoyl)-5,9-bis[[(4S,5R)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-4-oxazolyl]carbonyl]-14-(3-mercaptopropanoyl)-1,5,9,14-tetraazatetradecane, was synthesized and linked to ovalbumin (OVA) and bovine serum albumin (BSA). The antigenicity of the VIB microbial iron chelator conjugates and their iron complexes was evaluated. When mice were immunized with the resulting OVA-VIB conjugate, a selective and unequivocal antigenic response to the VIB hapten was observed; IgG monoclonal antibodies specific to the vibriobactin fragment of the BSA and OVA conjugates were isolated. The results are consistent with the idea that the isolated adducts of siderophores covalently linked to their bacterial outer membrane receptors represent a credible target for vaccine development.

  DOI：

  10.1021/jm900119q

文献信息

• Vibriobactin Antibodies: A Vaccine Strategy
  作者：Raymond J. Bergeron、Neelam Bharti、Shailendra Singh、James S. McManis、Jan Wiegand、Linda G. Green

  DOI：10.1021/jm900119q

  日期：2009.6.25

  A new target strategy in the development of bacterial vaccines, the induction of antibodies to microbial outer membrane ferrisiderophore complexes, is explored. A vibriobactin (VIB) analogue, with a thiol tether, -(2,3-dihydroxybenzoyl)-5,9-bis[[(4S,5R)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-4-oxazolyl]carbonyl]-14-(3-mercaptopropanoyl)-1,5,9,14-tetraazatetradecane, was synthesized and linked to ovalbumin (OVA) and bovine serum albumin (BSA). The antigenicity of the VIB microbial iron chelator conjugates and their iron complexes was evaluated. When mice were immunized with the resulting OVA-VIB conjugate, a selective and unequivocal antigenic response to the VIB hapten was observed; IgG monoclonal antibodies specific to the vibriobactin fragment of the BSA and OVA conjugates were isolated. The results are consistent with the idea that the isolated adducts of siderophores covalently linked to their bacterial outer membrane receptors represent a credible target for vaccine development.