N-succinimidyl sinapate | 56279-88-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-succinimidyl sinapate
• 英文别名: (2,5-dioxopyrrolidin-1-yl) 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• CAS: 56279-88-0
• 化学式: C₁₅H₁₅NO₇
• 分子量: 321.287
• InChiKey: BDDZVDBUESBHKP-UHFFFAOYSA-N

物化性质

• 沸点：
  484.9±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  102.37
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-succinimidyl sinapate 、 乙胺 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 以68%的产率得到ethylsinapamide
  参考文献：
  名称：

  vir-Gene-inducing activities of hydroxycinnamic acid amides in Agrobacterium tumefaciens

  摘要：

  Expression of Agrobacterium tumefaciens virulence genes and transformation of dicots by this organism are dependent upon host plant phenolic compounds. Several alkylsyringamides have recently been shown to be powerful inducers of these vir-genes. These synthetic amides, and especially ethylsyringamide, are much stronger inducers than syringic acid. In this work, four alkylamides derived from ferulic or sinapic acids were synthesized by a dicyclohexylcarbodiimide method and tested for their potential to induce vir-gene expression on A. tumefaciens strains harbouring virB::lacZ or virE::lacZ fusion plasmids. Their effectiveness was compared to that of ethylsyringamide and tyraminylferulamide, a naturally occurring amide in plants. Whatever the amine moiety of the amide (ethylamine, propylamine, tyramine or beta-alanine ethyl ester) conjugation of the acid functional group clearly diminished the toxicity to the bacteria of the respective acid at high concentration and thereby increased the vir-inducing potential. However, none of the inducers tested exhibited higher activity than acetosyringone, the reference compound for vir-gene induction, with the exception of ethylsyringamide at concentrations above 1 mM. When tested on Agrobacterium tumefaciens strain A348(pSM243cd), ethylferulamide and ethylsinapamide were more efficient than the corresponding phenolic acids but only above 100 mu M. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00209-x
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 芥子酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.5h， 生成 N-succinimidyl sinapate
  参考文献：
  名称：

  vir-Gene-inducing activities of hydroxycinnamic acid amides in Agrobacterium tumefaciens

  摘要：

  Expression of Agrobacterium tumefaciens virulence genes and transformation of dicots by this organism are dependent upon host plant phenolic compounds. Several alkylsyringamides have recently been shown to be powerful inducers of these vir-genes. These synthetic amides, and especially ethylsyringamide, are much stronger inducers than syringic acid. In this work, four alkylamides derived from ferulic or sinapic acids were synthesized by a dicyclohexylcarbodiimide method and tested for their potential to induce vir-gene expression on A. tumefaciens strains harbouring virB::lacZ or virE::lacZ fusion plasmids. Their effectiveness was compared to that of ethylsyringamide and tyraminylferulamide, a naturally occurring amide in plants. Whatever the amine moiety of the amide (ethylamine, propylamine, tyramine or beta-alanine ethyl ester) conjugation of the acid functional group clearly diminished the toxicity to the bacteria of the respective acid at high concentration and thereby increased the vir-inducing potential. However, none of the inducers tested exhibited higher activity than acetosyringone, the reference compound for vir-gene induction, with the exception of ethylsyringamide at concentrations above 1 mM. When tested on Agrobacterium tumefaciens strain A348(pSM243cd), ethylferulamide and ethylsinapamide were more efficient than the corresponding phenolic acids but only above 100 mu M. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00209-x