(-)-N-[4'-dihydroxy-(E)-cinnamoyl]-L-tyrosine | 77201-66-2

• 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: (-)-N-[4'-dihydroxy-(E)-cinnamoyl]-L-tyrosine
• 英文别名: N-(E)-p-coumaroyltyrosine；p-coumaroyl tyrosine；(-)-N-[4'-hydroxy-(E)-cinnamoyl]-L-tyrosine；(E)-N-(4-hydroxycinnamoyl)tyrosine；p-coumaroyl-N-tyrosine；deoxyclovamide；N-p-Coumaroyltyrosine；(2S)-3-(4-hydroxyphenyl)-2-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]propanoic acid
• CAS: 77201-66-2
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.337
• InChiKey: LEEDEKWKJVUWGA-YKXBDCQTSA-N

物化性质

• 熔点：
  137-139°C
• 沸点：
  673.6±55.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-香豆酸 在 吡啶 、 4-二甲氨基吡啶 、 氯化亚砜 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.33h， 生成 (-)-N-[4'-dihydroxy-(E)-cinnamoyl]-L-tyrosine
  参考文献：
  名称：

  Isolation, Structure Determination, Synthesis, and Sensory Activity of N-Phenylpropenoyl-l-amino Acids from Cocoa (Theobroma cacao)

  摘要：

  Application of chromatographic separation and taste dilution analyses recently revealed besides procyanidins a series of N-phenylpropenoyl amino acids as the key contributors to the astringent taste of nonfermented cocoa beans as well as roasted cocoa nibs. Because these amides have as yet not been reported as key taste compounds, this paper presents the isolation, structure determination, and sensory activity of these amino acid amides. Besides the previously reported (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine (clovamide), (-)-N-[4'-hydroxy-(E)-cinnamoyl]-L-tyrosine (deoxyclovamide), and (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-tyrosine, seven additional amides, namely, (+)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-aspartic acid, (+)-N-[4'-hydroxy-(E)-cinnamoyl]-L-aspartic acid, (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-glutamic acid, (-)-N-[4'-hydroxy-(E)-cinnamoyl]-L-glutamic acid, (-)-N-[4'-hydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine, (+)-N-[4'-hydroxy-3'-methoxy-(E)-cinnamoyl]-L-aspartic acid, and (+)-N-[(E)-cinnamoyl]-L-aspartic acid, were identified for the first time in cocoa products by means of LC-MS/MS, 1D/2D-NMR, UV-vis, CID spectroscopy, and polarimetry, as well as independent enantiopure synthesis. Using the recently developed half-tongue test, human recognition thresholds for the astringent and mouth-drying oral sensation were determined to be between 26 and 220 mu mol/L (water) depending on the amino acid moiety. In addition, exposure to light rapidly converted these [E]-configured N-phenylpropenoyl amino acids into the corresponding [2]-isomers, thus indicating that analysis of these compounds in food and plant materials needs to be performed very carefully in the absence of light to prevent artifact formation.

  DOI：

  10.1021/jf050458q

文献信息

• AMINO ACID DERIVATIVE
  申请人：Ookubo Tomohiro

  公开号：US20110172442A1

  公开（公告）日：2011-07-14

  The amino acid derivative of the present invention provides a novel compound that shows excellent analgesic action. The amino acid derivative of the present invention is a novel compound that shows excellent analgesic action to not only a model animal for nociceptive pains but also a model animal for neuropathic pains, so that the amino acid derivative is very useful as a drug for treating various pain diseases.

  本发明的氨基酸衍生物提供了一种显示出优异镇痛作用的新化合物。本发明的氨基酸衍生物是一种新化合物，不仅对于模拟伤害性疼痛的动物模型，而且对于模拟神经病理性疼痛的动物模型都显示出优异的镇痛作用，因此该氨基酸衍生物作为治疗各种疼痛疾病的药物非常有用。
• Structure-activity relationship of clovamide and its related compounds for the inhibition of amyloid β aggregation
  作者：Tatsuhiko Tsunoda、Mio Takase、Hideyuki Shigemori

  DOI：10.1016/j.bmc.2018.04.044

  日期：2018.7

  the structure-activity relationship of clovamide (1) for the inhibition of Aβ aggregation, we synthesized 1 and related compounds 2-11 through reaction between l-DOPA, d-DOPA, l-tyrosine, or l-phenylalanine and caffeic acid, p-coumaric acid, or cinnamic acid, and compounds 12 and 13 were derived from 1. Among tested compounds 1-13, those containing one or two catechol moieties exhibited potent anti-aggregation

  阿尔茨海默氏病（AD）是一种神经退行性疾病，其特征是淀粉样β蛋白（Aβ）聚集。Aβ通过β折叠形成聚集，并诱导针对神经元细胞的细胞毒性。因此，天然存在的化合物抑制Aβ聚集是治疗AD的有前途的策略。我们已经报道了具有两个或多个邻苯二酚部分的咖啡酰奎尼酸和苯乙酮类糖苷强烈抑制了Aβ聚集。从可可豆（Theobroma cacao L.）分离的含有两个邻苯二酚部分的环丙酰胺（1）被认为对Aβ聚集具有预防作用。为了研究氯丁酰胺（1）抑制Aβ聚集的构效关系，我们通过1-DOPA，d-DOPA，l-酪氨酸，或l-苯丙氨酸和咖啡酸，对香豆酸或肉桂酸，化合物12和13衍生自1。在测试的化合物1-13中，含有一个或两个邻苯二酚部分的化合物表现出强的抗聚集活性，而非儿茶酚类相关化合物几乎没有活性。这表明至少一个儿茶酚部分对于抑制Aβ42聚集是必不可少的，并且该活性根据儿茶酚部分的数目而增加。因此，clovamid
• Hydroxycinnamoyl Amino Acids Conjugates: A Chiral Pool to Distinguish Commercially Exploited Coffea spp.
  作者：Federico Berti、Luciano Navarini、Silvia Colomban、Cristina Forzato

  DOI：10.3390/molecules25071704

  日期：——

  The synthesis of five hydroxycinnamoyl amides (HCAs) was accomplished and their identification and quantification in the green coffee bean samples of Coffea arabica, Coffea canephora, and Coffea liberica was performed. The HCAs p-coumaroyl-N-tyrosine 1b, caffeoyl-N-phenylalanine 2b, caffeoyl-N-tyrosine 3b, and p-coumaroyl-N-tryptophan 4b were characteristic of the C. canephora species while caffeoyl-N-tryptophan 5b was present in both C. canephora and C. arabica, but with higher content in C. canephora. The HCAs presence was also analyzed in C. liberica for the first time and none of the targeted compounds was found, indicating that this species is very similar to C. arabica species. Between C. canephora samples from various origins, significant differences were observed regarding the presence of all the HCAs, with C. canephora from Tanzania containing all five derivatives.

  合成了五种羟基肉桂酰胺（HCAs），并对咖啡属（Coffea arabica，Coffea canephora和Coffea liberica）的绿咖啡豆样品进行了它们的鉴定和定量。HCAs对C. canephora物种具有特征性，其中p-香豆酰-N-酪氨酸1b，咖啡酰-N-苯丙氨酸2b，咖啡酰-N-酪氨酸3b和p-香豆酰-N-色氨酸4b。咖啡酰-N-色氨酸5b存在于C. canephora和C. arabica中，但在C. canephora中含量更高。首次分析了C. liberica中的HCAs存在，并且没有发现任何目标化合物，表明该物种与C. arabica物种非常相似。在来自不同地区的C. canephora样品中，观察到所有HCAs的存在方面存在显着差异，坦桑尼亚的C. canephora含有所有五种衍生物。
• Genetically altered alfalfa producing clovamide and/or related hydroxycinnamoyl amides
  申请人：The United States of America, as represented by the Secretary of Agriculture

  公开号：US10253324B2

  公开（公告）日：2019-04-09

  Two novel cDNAs for two different genes, HDT1 and HDT2, are isolated from red clover and sequenced. Both HDT1 and HDT2 encode hydroxycinnamoyl-CoA:L-DOPA/tyrosine hydroxycinnamoyl transferase (HDT) which enzymatically produces clovamide and/or related hydroxycinnamoyl amides. Clovamide and related hydroxycinnamoyl amides reduce post-harvest protein degradation. Genetically altered alfalfa plants containing an expression cassette containing a cDNA encoding HDT1 or HDT2 are generated. These genetically altered alfalfa plants produce hydroxycinnamoyl-CoA:L-DOPA/tyrosine hydroxycinnamoyl transferase, which in turn produces clovamide and/or related hydroxycinnamoyl amides.

  从红三叶中分离出两个不同基因 HDT1 和 HDT2 的新型 cDNA，并对其进行了测序。HDT1 和 HDT2 都编码羟基肉桂酰-CoA:L-DOPA/酪氨酸羟基肉桂酰转移酶（HDT），它能酶促产生氯酰胺和/或相关的羟基肉桂酰酰胺。氯酰胺和相关的羟基肉桂酰酰胺可减少收获后蛋白质的降解。基因改变的苜蓿植株含有一个表达盒，其中包含编码 HDT1 或 HDT2 的 cDNA。这些基因改变的苜蓿植物会产生羟基肉桂酰-CoA:L-DOPA/酪氨酸羟基肉桂酰转移酶，进而产生氯酰胺和/或相关的羟基肉桂酰酰胺。
• MEDIZINISCHE VERWENDUNG VON N-PHENYLPROPENOYL-AMINOSÄUREDERIVATEN
  申请人：Westfälische Wilhelms-Universität Münster

  公开号：EP2040692B1

  公开（公告）日：2012-09-19