Boc-Ala-Ala-Ala-OH | 27317-70-0

• 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: Boc-Ala-Ala-Ala-OH
• 英文别名: Boc-Ala-Ala-Ala；N-(tert-Butoxycarbonyl)-L-alanyl-L-alanyl-L-alanine；(2S)-2-[[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoyl]amino]propanoic acid
• CAS: 27317-70-0
• 化学式: C₁₄H₂₅N₃O₆
• 分子量: 331.369
• InChiKey: GKLRPTKGJVEDRU-CIUDSAMLSA-N

物化性质

• 沸点：
  622.3±50.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Ala-Ala-Ala-OH 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 41.5h， 生成 N^α-tert-butoxycarbonyl-L-alanyl-L-alanyl-L-alanyl-L-lysyl-L-alanyl-(N^ε-(benzo-18-crown-6)-4-carbonyl)-L-lysyl-L-alanine methyl ester acetate
  参考文献：
  名称：

  Design and synthesis of novel peptides bearing a host and a guest side chains

  摘要：

  The synthesis of model heptapeptides bearing a host and a guest side chains at different positions is reported. These peptidic structures were designed in such a way that specific backbone; conformations could be induced and stabilized by cooperative side chain interactions. Although circular dichroism studies demonstrated that intra- and intermolecular host guest interactions are involved in the stabilization of the peptidic conformation, they are not strong enough to induce a complete conformational reorganization.

  DOI：

  10.1016/s0040-4020(01)80813-9
• 作为产物：
  描述：

  叔丁氧羰基-丙氨酰-丙氨酸 在 sodium hydroxide 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 Boc-Ala-Ala-Ala-OH
  参考文献：
  名称：

  Design and synthesis of novel peptides bearing a host and a guest side chains

  摘要：

  The synthesis of model heptapeptides bearing a host and a guest side chains at different positions is reported. These peptidic structures were designed in such a way that specific backbone; conformations could be induced and stabilized by cooperative side chain interactions. Although circular dichroism studies demonstrated that intra- and intermolecular host guest interactions are involved in the stabilization of the peptidic conformation, they are not strong enough to induce a complete conformational reorganization.

  DOI：

  10.1016/s0040-4020(01)80813-9

文献信息

• Phase-transfer reagents as C-terminal protecting groups; facile incorporation of free amino acids or peptides into peptide sequences
  作者：Shui-Tein Chen、Kung-Tsung Wang

  DOI：10.1039/c39900001045

  日期：——

  Phase-transfer reagents (basic, neutral, and acidic) can effect temporary protection of carboxy groups by salt formation in C-terminal free amino acids or peptides during peptide synthesis; the use of acidic or neutral phase-transfer reagents as the C-terminal protecting group will not affect the nucleophilicity of the amino group of the salts thus prepared in an organic solvent.

  相转移试剂（碱性，中性和酸性）可通过在肽合成过程中在C端游离氨基酸或肽中形成盐来暂时保护羧基。使用酸性或中性相转移试剂作为C-末端保护基不会影响在有机溶剂中如此制得的盐的氨基的亲核性。
• Peptide-tethered monodentate and chelating histidylidene metal complexes: synthesis and application in catalytic hydrosilylation
  作者：Angèle Monney、Flavia Nastri、Martin Albrecht

  DOI：10.1039/c3dt50424g

  日期：——

  abstraction from the rhodium centre, while tyrosine remained non-coordinating under identical conditions. High catalytic activities in hydrosilylation were achieved with all peptide-based rhodium complexes. The cationic SMet,CHis*-bidentate peptide rhodium catalyst outperformed the monodentate neutral peptide complexes and constitutes one of the most efficient rhodium carbene catalysts for hydrosilylation

  的Ñ δ，Ñ ε -dimethylated histidinium盐（他*）被拴在寡肽和金属化，以形成的Ir（III）和Rh（我）NHC络合物。基于肽的组氨酸二亚胺配合物仅含有丙氨酸，合成了Ala–Ala–His * – [M]和Ala–Ala–Ala–His * – [M]（[M] = 铑（鳕鱼）Cl，Ir（Cp *）Cl 2）以及具有潜在螯合作用的寡肽复合物蛋氨酸 和酪氨酸残基，Met–Ala–Ala–His * –铑（鳕鱼）Cl 和 提尔–Ala–Ala–His * –铑（鳕鱼）Cl。从铑中心提取卤化物诱导了含有蛋氨酸的组氨酸亚基配体的螯合，而酪氨酸在相同条件下仍然不协调。所有基于肽的铑配合物均能实现氢化硅烷化中的高催化活性。阳离子S Met，C His *-双齿肽铑催化剂的性能优于单齿中性肽络合物，构成了氢化硅烷化最有效的铑卡宾催化剂之一，为肽在催化中用作N-杂环卡宾配体提供了新的机会。
• Studies on flavored peptides. VIII. Mechanism for the bitter tasting potency of peptides using O-aminoacyl sugars as model compounds.
  作者：Masahiro TAMURA、Takafumi MIYOSHI、Naoko MORI、Keisuke KINOMURA、Michihiko KAWAGUCHI、Norio ISHIBASHI、Hideo OKAI

  DOI：10.1271/bbb1961.54.1401

  日期：——

  In order to study the role of hydrophobicity in bitter peptides, several O-aminoacyl sugars, in which amino acids or peptides were attached to the 2- and 3-position of methyl α-D-glucopyranoside, were synthesized and sensory analyses were carried out. It was found that the bitterness increased as the hydrophobicity of compounds increased, implying that the bitterness receptor recognizes the hydrophobicity of bitter peptides. A structure for the bitterness receptor is also discussed.

  为了研究疏水性在苦味肽中的作用，合成了几种 O-氨基酰基糖，其中氨基酸或肽附着在甲基 α-D 吡喃葡萄糖苷的 2 位和 3 位上，并进行了感官分析。结果发现，随着化合物疏水性的增加，苦味也随之增加，这意味着苦味受体能识别苦味肽的疏水性。此外，还讨论了苦味受体的结构。
• Modifying oligoalanine conformation by replacement of amide to ester linkage
  作者：Takahiro Hongen、Tohru Taniguchi、Kenji Monde

  DOI：10.1002/chir.22823

  日期：2018.4

  a rigid left‐handed helical structure. In this study, oligo(lactic acid) was incorporated into oligoalanine sequences and their conformations were studied by vibrational circular dichroism and electronic circular dichroism spectroscopy. The results suggested that oligo(lactic acid) moiety in these sequences maintains a left‐handed helix and increases the conformational propensity of the oligoalanine

  Oligo（乳酸）是短寡丙氨酸序列的酯类似物，采用刚性的左手螺旋结构。在这项研究中，低聚乳酸被纳入了低聚丙氨酸序列，并通过振动圆二色性和电子圆二色性光谱研究了它们的构象。结果表明，这些序列中的低聚（乳酸）部分保持左旋螺旋，并增加了低聚丙氨酸部分的构象倾向，形成左旋多脯氨酸II型螺旋状。还研究了低聚（乳酸）部分的手性对于低聚丙氨酸构象的重要性。这项研究中获得的结果应可用于开发功能比普通肽更好的含酯寡肽。
• Prodrugs of excitatory amino acids
  申请人：ELI LILLY AND COMPANY

  公开号：EP1310482A1

  公开（公告）日：2003-05-14

  This invention relates to synthetic excitatory amino acid prodrugs of the formula I wherein R11 is CO2R14 and R12 is hydrogen or fluoro; or R11 is hydrogen or fluoro and R12 is CO2R14; R13 and R14 are, independently, hydrogen, (1-10C) alkyl, (2-4C) alkenyl, aryl or arylalkyl; A is (Q)p-; p is any integer from 1-10; and Q is independently selected, each time taken, from the group amino acyl; provided that the compound is not one on which R11 is CO2R14; R12, R13 and R14 are hydrogen; p is 1; and Q is L-alanyl; or a pharmaceutically acceptable salt thereof and processes for their preparation. The invention further relates to methods of using, and pharmaceutical composition comprising, the compounds for the treatment of neurological disorders and psychiatric disorders.

  本发明涉及公式I的合成兴奋性氨基酸前药，其中R11为CO2R14且R12为氢或氟；或R11为氢或氟且R12为CO2R14；R13和R14分别为氢、(1-10C)烷基、(2-4C)烯基、芳基或芳基烷基；A为(Q)p-；p为1-10的任意整数；Q每次从氨基酰基组中独立选择；前提是该化合物不是R11为CO2R14；R12、R13和R14为氢；p为1；Q为L-丙氨酰；或其药学上可接受的盐及其制备方法。本发明还涉及使用这些化合物以及包含这些化合物的药物组合物治疗神经疾病和精神疾病的方法。