L-丙氨酰-L-丙氨酰-L-丙氨酰-D-丙氨酰-L-丙氨酸

• 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
• 中文名称: L-丙氨酰-L-丙氨酰-L-丙氨酰-D-丙氨酰-L-丙氨酸
• 英文名称: Penta-L-Alanin
• 英文别名: AAAAA；Ala5；pentaalanine；(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-azaniumylpropanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoate
• 化学式: C₁₅H₂₇N₅O₆
• 分子量: 373.409
• InChiKey: XXAUOPDVAKGRPR-WYCDGMCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  180
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  L-丙氨酰-L-丙氨酰-L-丙氨酰-D-丙氨酰-L-丙氨酸 在 溶剂黄146 作用下， 反应 36.0h， 生成 N-acetylpenta-L-alanyl methyl ester
  参考文献：
  名称：

  快速加热质谱中的挥发动力学：某些氢键物种的活化能

  摘要：

  DOI：

  10.1021/j100235a029
• 作为产物：
  描述：

  tetra-L-alanine 在 sodium hydroxide 、 氨 、 水 、 lithium bromide 作用下， 生成 L-丙氨酰-L-丙氨酰-L-丙氨酰-D-丙氨酰-L-丙氨酸
  参考文献：
  名称：

  Abderhalden; Gohdes, Fermentforschung, 1931, vol. 13, p. 55

  摘要：

  DOI：

文献信息

• Mechanism study on the Oligomerization of Amino Acids into Peptides by Phosphorus Trichloride
  作者：Wenjie Zhao、Dongxin Zhao、Kui Lu

  DOI：10.1080/10426500701807467

  日期：2008.1.14

  As treated by phosphorus trichloride, amino acids could oligomerize into polypeptides. Based on the results obtained by 31P-NMR and ESI-MS/MS, a possible reaction mechanism was proposed. The mechanism might undergo a penta-coordinated phosphorus intermediat. The activated amino acid was a five-membered cyclic penta-coordinated phosphorus intermediate. The nucleophilic attack of the amino group from

  经三氯化磷处理后，氨基酸可寡聚化为多肽。基于31P-NMR和ESI-MS/MS的结果，提出了可能的反应机理。该机制可能会经历五配位的磷中间体。活化的氨基酸是五元环状五配位磷中间体。氨基酸或肽的氨基对中间体羰基的亲核攻击导致肽的形成并释放出一当量的二氯化磷酸。反应序列的重复产生了一系列寡肽。
• Intramolecular Hydrogen Transfer from the Alpha-Carbon (Cα) and Backbone Amide Nitrogen (N_b) to Form c- and y-Ions in Negative-Ion CID of Peptides
  作者：Asaki Kagoshima、Kanako Sekimoto、Mitsuo Takayama

  DOI：10.1007/s13361-019-02245-z

  日期：2019.9.1

  high-resolution orbitrap mass spectrometer. The rate of deuterium transfer obtained indicates that over 50% of the hydrogen was originated from the backbone amide nitrogen, with the residual hydrogen coming from the backbone Cα. It is clear that the hydrogen does not originate from the side chain Cβ. It is hypothesized that the intramolecular hydrogen transfer to form negative c- and y-ions takes place via 3-, 4-

  已使用Cα-，Cβ-和主链酰胺（Nb）氘代肽AAA（d3）检查了在负离子CID实验中通过肽进行分子内氢转移而形成c和y离子时形成氢的来源。 AA，AAG（d2）AA，AAAG（d2）A和AAAAA-d7，以及其他五个肽。通过氘化残留物进行氘转移产生的c和y离子被检测到，并通过高分辨率orbitrap质谱仪获得的精确m / z值进行了鉴定。获得的氘转移速率表明，超过50％的氢氢来自骨架酰胺氮，而剩余的氢则来自骨架Cα。显然，氢不是源自侧链Cβ。
• Method for producing peptide
  申请人：Hamari Chemicals, Ltd.

  公开号：US11084846B2

  公开（公告）日：2021-08-10

  An object of the present invention is to provide a novel solid phase peptide synthesis method for synthesizing a large amount of a peptide. Another object of the present invention is to provide a novel solid phase peptide synthesis method for synthesizing a high-purity long-chain peptide. Still another object of the present invention is to provide a novel solid phase peptide synthesis method causing fewer side reactions. The present invention relates to a method for producing a peptide, and the method comprises solid-phase synthesis of a peptide under stirring with a centrifugal stirrer having no impeller.

  本发明的一个目的是提供一种用于合成大量多肽的新型固相多肽合成方法。本发明的另一个目的是提供一种合成高纯度长链肽的新型固相肽合成方法。本发明的另一个目的是提供一种可减少副反应的新型固相肽合成方法。本发明涉及一种生产多肽的方法，该方法包括在没有叶轮的离心搅拌器的搅拌下进行多肽的固相合成。
• Dibenzoyl peroxide-induced photodecarboxylation of amino acids and peptides. A spin-trapping study
  作者：Ionel Rosenthal、Magdi M. Mossoba、Peter Riesz

  DOI：10.1021/j150616a021

  日期：1981.8
• Structure and Dynamics of the Homologous Series of Alanine Peptides:  A Joint Molecular Dynamics/NMR Study
  作者：Jürgen Graf、Phuong H. Nguyen、Gerhard Stock、Harald Schwalbe

  DOI：10.1021/ja0660406

  日期：2007.2.1

  The phi,psi backbone angle distribution of small homopolymeric model peptides is investigated by a joint molecular dynamics (MD) simulation and heteronuclear NMR study. Combining the accuracy of the measured scalar coupling constants and the atomistic detail of the all-atom MD simulations with explicit solvent, the thermal populations of the peptide conformational states are determined with an uncertainty of < 5 %. Trialanine samples mainly (similar to 90%) a poly-L-proline II helix-like structure, some (similar to 10%) beta extended structure, but no alpha(R) helical conformations. No significant change in the distribution of conformers is observed with increasing chain length (Ala(3) to Ala(7)). Trivaline samples all three major conformations significantly. Tryglycine samples the four corner regions of the Ramachandran space and exists in a slow conformational equilibrium between the cis and trans conformation of peptide bonds. The backbone angle distribution was also studied for the segment Ala(3) surrounded by either three or eight amino acids on both N- and C-termini from a sequence derived from the protein hen egg white lysozyme. While the conformational distribution of the central three alanine residues in the 9mer is similar to that for the small peptides Ala(3)-Ala(7,) major differences are found for the 19mer, which significantly (30-40%) samples alpha(R) helical stuctures.