caffeic acid N-hydroxysuccinimide ester

• 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: caffeic acid N-hydroxysuccinimide ester
• 英文别名: 2,5-Dioxopyrrolidin-1-yl 3-(3,4-dihydroxyphenyl)acrylate；(2,5-dioxopyrrolidin-1-yl) (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₁₃H₁₁NO₆
• 分子量: 277.233
• InChiKey: RYTGOIQSDYIEOO-QHHAFSJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Trp-Lys-Asp-Phe-NH2 、 caffeic acid N-hydroxysuccinimide ester 在 N-甲基吗啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-Trp-Lys(coumaroyl(3-OH))(coumaroyl(3-OH))-Asp-Phe-NH2
  参考文献：
  名称：

  Development of potent and selective CCK-A receptor agonists from Boc-CCK-4: tetrapeptides containing Lys(N.epsilon.)-amide residues

  摘要：

  A series of Boc-CCK-4 derivatives represented by the general structure Boc-Trp-Lys(N(epsilon)-COR)-Asp-Phe-NH2, where R is an aromatic, heterocyclic, or aliphatic group, are potent and selective CCK-AT receptor agonists. These amide-bearing compounds complement the previously described urea-based tetrapeptides (Shiosaki et al. J. Med. Chem. 1991, 34, 2837-2842); structure-activity studies revealed parallel as well as divergent trends between these two series. A significant correlation was observed between pancreatic binding affinity and the resonance constant R of the phenyl substituent in one particular series of derivatives. Sulfation of phenolic amides appended onto the epsilon-amino group of the lysine did not affect affinity for the CCK-AT receptor in contrast to the 500-fold increase in binding potency observed upon sulfation of CCK-8, suggesting that the lysine appendage and the sulfated tyrosine in CCK-8, both key structural elements that impart high affinity for the CCK-A receptor, are interacting differently with the receptor. The amide-bearing tetrapeptides are full agonists relative to CCK-8 in stimulating pancreatic amylase release while being partial agonists in eliciting phosphoinositide (PI) hydrolysis. Both effects were blocked by selective CCK-A receptor antagonists.

  DOI：

  10.1021/jm00089a010
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 TRANS-咖啡酸 在 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 为溶剂， 反应 24.0h， 生成 caffeic acid N-hydroxysuccinimide ester
  参考文献：
  名称：

  植物提取物中羟基肉桂酰辅酶a硫酯的磷酸水解

  摘要：

  摘要 在大麦幼苗提取物中，对香豆酰-CoA 迅速水解为对香豆酰-脱磷酸-CoA、对-香豆酰-4'-磷酸泛酰巯基乙胺和对香豆酰-泛酰巯基乙胺。对香豆酰-4'-磷酸泛酰巯基乙胺在对香豆酰-胍丁胺形成过程中作为胍丁香豆酰转移酶的底物具有活性，但对香豆酰-泛酰巯基乙胺是无活性的。磷酸化水解可被无机焦磷酸盐、氟化钠和嘌呤核苷酸部分抑制。还描述了合成羟基肉桂酸的 N-羟基琥珀酰亚胺酯的简化方法，用于合成 CoA 硫酯。

  DOI：

  10.1016/0031-9422(84)83072-1

文献信息

• The phosphohydrolysis of hydroxycinnamoyl-coenzyme a thioesters in plant extracts
  作者：Jonathan Negrel、Terence A. Smith

  DOI：10.1016/0031-9422(84)83072-1

  日期：1984.1

  Abstract In barley seedling extracts, p -coumaroyl-CoA is rapidly hydrolysed to p -coumaroyl-dephospho-CoA, p -coumaroyl-4′-phosphopantetheine and p -coumaroyl-pantetheine. p -Coumaroyl-4′-phosphopantetheine is active as a substrate of agmatine coumaroyl transferase in the formation of p -coumaroyl-agmatine, but p -coumaroyl-pantetheine is inactive. The phosphohydrolysis can be partly inhibited by inorganic

  摘要 在大麦幼苗提取物中，对香豆酰-CoA 迅速水解为对香豆酰-脱磷酸-CoA、对-香豆酰-4'-磷酸泛酰巯基乙胺和对香豆酰-泛酰巯基乙胺。对香豆酰-4'-磷酸泛酰巯基乙胺在对香豆酰-胍丁胺形成过程中作为胍丁香豆酰转移酶的底物具有活性，但对香豆酰-泛酰巯基乙胺是无活性的。磷酸化水解可被无机焦磷酸盐、氟化钠和嘌呤核苷酸部分抑制。还描述了合成羟基肉桂酸的 N-羟基琥珀酰亚胺酯的简化方法，用于合成 CoA 硫酯。
• DOTA COMPOUNDS AND USES THEREOF
  申请人：Memorial Sloan-Kettering Cancer Center

  公开号：US20210188787A1

  公开（公告）日：2021-06-24

  Provided herein are DOTA-containing compounds (e.g., compounds of Formula (I)) and complexes that are reactive with an enzyme activator (e.g., a peroxidase) and covalently bind a target analyte (e.g., a protein) in a catalyzed reporter deposition assaying method. The DOTA-containing compounds and complexes are advantageous over existing reporter compounds and complexes because the DOTA moiety allows detection of the reporter moiety by use of mass spectrometry imaging microscopy.
• Development of potent and selective CCK-A receptor agonists from Boc-CCK-4: tetrapeptides containing Lys(N.epsilon.)-amide residues
  作者：Kazumi Shiosaki、Chun Wel Lin、Hana Kopecka、Richard A. Craig、Bruce R. Bianchi、Thomas R. Miller、David G. Witte、Michael Stashko、Alex M. Nadzan

  DOI：10.1021/jm00089a010

  日期：1992.5

  A series of Boc-CCK-4 derivatives represented by the general structure Boc-Trp-Lys(N(epsilon)-COR)-Asp-Phe-NH2, where R is an aromatic, heterocyclic, or aliphatic group, are potent and selective CCK-AT receptor agonists. These amide-bearing compounds complement the previously described urea-based tetrapeptides (Shiosaki et al. J. Med. Chem. 1991, 34, 2837-2842); structure-activity studies revealed parallel as well as divergent trends between these two series. A significant correlation was observed between pancreatic binding affinity and the resonance constant R of the phenyl substituent in one particular series of derivatives. Sulfation of phenolic amides appended onto the epsilon-amino group of the lysine did not affect affinity for the CCK-AT receptor in contrast to the 500-fold increase in binding potency observed upon sulfation of CCK-8, suggesting that the lysine appendage and the sulfated tyrosine in CCK-8, both key structural elements that impart high affinity for the CCK-A receptor, are interacting differently with the receptor. The amide-bearing tetrapeptides are full agonists relative to CCK-8 in stimulating pancreatic amylase release while being partial agonists in eliciting phosphoinositide (PI) hydrolysis. Both effects were blocked by selective CCK-A receptor antagonists.
• New series of avenanthramides in oat seed
  作者：Atsushi Ishihara、Kana Kojima、Takeshi Fujita、Yuya Yamamoto、Hiromitsu Nakajima

  DOI：10.1080/09168451.2014.946390

  日期：2014.12.2

  Avenanthramides are characteristic constituents of oat seeds. We analyzed the methanol extract of oat seeds by HPLC and detected three compounds 1, 2, and 3 eluted at retention times similar to avenanthramides. The three compounds were purified by column chromatography and HPLC. Spectroscopic analyses of 1, 2, and 3 suggested that they are amides of 4,5-dihydroxyanthranilic acid with caffeic, p-coumaric, and ferulic acids, respectively. Their identities were confirmed by comparing spectra and chromatographic behavior with compounds synthesized from 4,5-dihydroxyanthranilic acid and N-hyrdroxysuccinimide esters of hydroxycinnamic acids. LC-MS/MS analysis with multiple reaction monitoring showed that the amounts of 1, 2, and 3 were 16.5–26.9% of corresponding avenanthamides with 5-hydroxyanthranilic acid. Compounds 1, 2, and 3 showed stronger 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activity than the corresponding avenanthramides with 5-hydroxyanthranilic acid, indicating the involvement of 4,5-dihydroxyanthranilic acid moiety in the scavenging of DPPH radicals.

  燕麦籽中的燕麦苷是其特有的成分。我们通过高效液相色谱法分析了燕麦籽的甲醇提取物，检测到三种化合物1、2和3，它们在保留时间上与燕麦苷相似。通过柱层析和高效液相色谱法纯化了这三种化合物。对1、2和3的光谱分析表明，它们分别是4,5-二羟基蒽醌酸与咖啡酸、对香豆酸和香草酸的酰胺。通过将4,5-二羟基蒽醌酸和羟基肉桂酸类的N-羟基琥珀酰亚胺酯合成的化合物与光谱和色谱行为进行比较，证实了它们的身份。多反应监测的LC-MS/MS分析表明，1、2和3的含量是相应燕麦苷的16.5-26.9%，这些燕麦苷含有5-羟基蒽醌酸。化合物1、2和3的2,2-二苯基-1-芘肼（DPPH）自由基清除活性比含有5-羟基蒽醌酸的相应燕麦苷更强，表明4,5-二羟基蒽醌酸基团参与了清除DPPH自由基的过程。