N-caproylphenylalanine | 21888-33-5

• 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-caproylphenylalanine
• 英文别名: N-n-hexanoyl (L)-phenylalanine；N-hexanoyl-L-phenylalanine；N-n-caproyl-L(+)-phenylalanine；(2S)-2-(hexanoylamino)-3-phenylpropanoic acid
• CAS: 21888-33-5
• 化学式: C₁₅H₂₁NO₃
• mdl: MFCD16377832
• 分子量: 263.337
• InChiKey: ZVFSJAMJPGFMOA-ZDUSSCGKSA-N

物化性质

• 熔点：
  137-139 °C
• 沸点：
  481.5±38.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.466
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-caproylphenylalanine 生成 L-苯丙氨酸
  参考文献：
  名称：

  KANG, SHINWON;MINEMATSU, YOSHIHIRO;SHIMOHIGASHI, YASUYUKI;WAKI, MICHINORI+, MEM. FAC. SCI. KYUSHU UNIV., 16,(1987) N 1, 61-68

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl N-hexanoyl-L-phenylalanate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.0h， 以78%的产率得到N-caproylphenylalanine
  参考文献：
  名称：

  Molecular mechanism of physical gelation of hydrocarbons by fatty acid amides of natural amino acids

  摘要：

  A variety of fatty acid amides of different naturally occurring L-amino acids have been synthesized and they are found to form gels with various hydrocarbons. The gelation properties of these compounds were studied by a number of physical methods including FTIR spectroscopy, X-ray diffraction, scanning electron microscopy, differential scanning calorimetry, rheology, and it was found that gelation depended critically on the fatty acid chain length and the nature of the amino acid. Among them L-alanine based gelators were found to be the most efficient and versatile gelators as they self-assemble into a layered structure to form the gel network. Mechanisms for the assembly and formation of gels from these molecules are discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.028

文献信息

• Repurposing the 3‐Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification
  作者：Mengyi Zhu、Lijuan Wang、Jing He

  DOI：10.1002/anie.202010042

  日期：2021.1.25

  molecules with novel skeletons, but also to identify the enzymes that catalyze diverse chemical reactions. Exploring the substrate promiscuity and catalytic mechanism of those biosynthetic enzymes facilitates the development of potential biocatalysts. SfaB is an acyl adenylate‐forming enzyme that adenylates a unique building block, 3‐isocyanobutanoic acid, in the biosynthetic pathway of the diisonitrile

  微生物天然产物的基因组挖掘使化学家不仅能够发现具有新颖骨架的生物活性分子，而且能够识别催化多种化学反应的酶。探索这些生物合成酶的底物混杂性和催化机理有助于开发潜在的生物催化剂。SfaB是一种形成酰基腺苷酸的酶，可在由硫链霉菌产生的二异腈自然产物SF2768的生物合成途径中，对独特的结构单元3-异氰基丁酸进行腺苷酸化。，并且该AMP连接酶被证明可以接受各种短链脂肪酸（SCFA）。在本文中，我们将SfaB重新用于催化那些SCFA与各种胺或硫醇亲核试剂之间的酰胺化或硫酯化反应，从而提供了另一种酶促方法来体外制备相应的酰胺和硫酯。
• Structure–activity relationship study of syringolin A as a potential anticancer agent
  作者：Takuya Chiba、Akira Matsuda、Satoshi Ichikawa

  DOI：10.1016/j.bmcl.2015.06.015

  日期：2015.11

  A detailed structure–activity relationship of syringolin A (1), which is a promising antitumor natural product, was described. We previously developed syringolin A analog 2 as a potent proteasome inhibitor by the structure-based drug design of syringolin A. In this Letter, we synthesized a range of analogs of 2, having a different length of the lipophilic chain and substituted aryl group, and their

  详细描述了丁香脂素A（1）的结构与活性之间的关系，紫丁香酚A是一种很有前途的抗肿瘤天然产物。我们先前通过丁香酚A的基于结构的药物设计，开发了丁香酚A的类似物2作为有效的蛋白酶体抑制剂。在这封信中，我们合成了一系列2的类似物，它们具有不同的亲脂性链长和取代的芳基，并且评估了它们对人类癌细胞的细胞毒性。事实证明，这些修饰极大地影响了细胞毒性。进一步的优化将导致开发新型的蛋白酶体抑制剂。
• Amide Bond Formation Using 4-Coumarate: CoA Ligase from <i>Arabidopsis thaliana</i>
  作者：Takahiro Mori、Kiyofumi Wanibuchi、Hiroyuki Morita、Ikuro Abe

  DOI：10.1248/cpb.c21-00404

  日期：2021.8.1

  Amide bond formation is one of the most fundamental reactions in organic chemistry, and amide bonds constitute the key functional groups in natural products, peptides, and pharmaceuticals. Here we demonstrate the chemoenzymatic syntheses of 4-coumaroyl- and hexanoyl-amino acids, using 4-coumarate: CoA ligase from the model plant Arabidopsis thaliana (At4CL2). At4CL2 accepts 4-coumaric acid and hexanoic

  酰胺键的形成是有机化学中最基本的反应之一，酰胺键构成了天然产物、多肽和药物中的关键官能团。在这里，我们展示了使用 4-香豆酸：来自模式植物拟南芥(At4CL2) 的CoA 连接酶的 4-香豆酰和己酰氨基酸的化学酶促合成。At4CL2 接受 4-香豆酸和己酸作为羧酸盐底物以生成酰基腺苷酸，其被氨基酸的氨基捕获以提供一系列N-酰基酰胺。这项研究显示了 4CL 作为生物催化剂的应用潜力，可以产生一系列具有生物活性的酰胺化合物。 全尺寸图像
• Composition containing a penem or carbapenem antibiotic
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0178911A2

  公开（公告）日：1986-04-23

  57 Administration of an N-acylated amino acid (ornithine, lysine, phenylglycine or phenylalanine) in association with a penem or carbapenem antibiotic relieves or eliminates the renal problems associated with administration of the antibiotic alone. The amino acid and antibiotic may be formulated together as a composition or administered separately, either simultaneously or sequentially. A pharmaceutical composition may be prepared simply by mixing the two components.

  57 将 N-酰化氨基酸（鸟氨酸、赖氨酸、苯甘氨酸或苯丙氨酸）与培南类或碳青霉烯类抗生素联合给药，可缓解或消除与单独给药抗生素相关的肾脏问题。 氨基酸和抗生素可一起配制成组合物，也可同时或依次单独给药。 只需将两种成分混合即可制备成药物组合物。
• KANG, SHINWON;MINEMATSU, YOSHIHIRO;SHIMOHIGASHI, YASUYUKI;WAKI, MICHINORI+, MEM. FAC. SCI. KYUSHU UNIV., 16,(1987) N 1, 61-68
  作者：KANG, SHINWON、MINEMATSU, YOSHIHIRO、SHIMOHIGASHI, YASUYUKI、WAKI, MICHINORI+

  DOI：——

  日期：——