tetra-L-alanine | 926-78-3

• 物质功能分类: 生物化工 - 多肽
• 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: tetra-L-alanine
• 英文别名: L-alanyl-L-alanyl-L-alanyl-L-alanine；Ala-Ala-Ala-Ala；tetraalanine；AAAA；Ala4；A4；(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-azaniumylpropanoyl]amino]propanoyl]amino]propanoyl]amino]propanoate
• CAS: 926-78-3；926-79-4；5874-82-8；5874-83-9；5874-84-0；5874-85-1；6062-67-5；6062-68-6；6120-80-5；6618-84-4；6621-00-7；6759-32-6；10145-91-2；14017-24-4；91741-19-4；91741-20-7
• 化学式: C₁₂H₂₂N₄O₅
• mdl: MFCD00066035
• 分子量: 302.33
• InChiKey: ZHRZLXZJVUFLNY-XAMCCFCMSA-N

物化性质

• 溶解度：
  可溶于酸性水溶液（轻微）、水（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  151
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tetra-L-alanine 在 溶剂黄146 作用下， 反应 36.0h， 生成 Ac-Ala-Ala-Ala-Ala-OMe
  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：

  Fmoc-L-丙氨酸 生成 tetra-L-alanine
  参考文献：
  名称：

  Structure and Dynamics of the Homologous Series of Alanine Peptides:  A Joint Molecular Dynamics/NMR Study

  摘要：

  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.

  DOI：

  10.1021/ja0660406
• 作为试剂：
  描述：

  反式-查耳酮 在 Tentagel S NH₂ 、 tetra-L-alanine 、 双氧水 作用下， 以 sodium hydroxide 为溶剂， 生成 (2S,3R)-2,3-epoxy-1,3-diphenylpropan-1-one 、 (2R,3S)-epoxy-1,3-diphenylpropan-1-one
  参考文献：
  名称：

  短固相结合肽催化的高对映选择性烯酮环氧化：肽螺旋的主要作用。

  摘要：

  合成了一系列L-Leu 1-20-mers，带有1-5个N-末端Gly残基的肽以及（S）-β（3）-Leu和（1R，2R）-2-氨基环己烷羧酸的低聚物TentaGel S NH（2）。发现五个L-Leu残留物足以催化96-98％ee的查尔酮的朱丽亚-可伦娜环氧化。实验和分子建模表明，催化作用是通过烯酮与N末端的结合来实现的，并且肽的螺旋度通过氢过氧化阴离子的面选择性传递决定了环氧化物的构型。[反应：看文字]

  DOI：

  10.1021/ol0166451

文献信息

• Diastereoselectivity in prebiotically relevant 5(4H)-oxazolone-mediated peptide couplings
  作者：Damien Beaufils、Grégoire Danger、Laurent Boiteau、Jean-Christophe Rossi、Robert Pascal

  DOI：10.1039/c3cc49580a

  日期：——

  out as the first part of a systems chemistry investigation of potential paths for symmetry breaking. Substantial diastereomeric excesses result from a fast epimerization of the 5(4H)-oxazolone intermediate in aqueous solution.

  进行了可能的益生元肽形成反应的立体化学研究，作为系统化学研究对称断裂潜在途径的第一部分。非对映异构体的大量过量是由于5（4H）-恶唑酮中间体在水溶液中的快速差向异构化。
• 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。
• CHEMICAL LIGATION BY RING OPENING OF OXO-THIOMORPHOLINES
  申请人：Harwood Laurence Marius

  公开号：US20130267681A1

  公开（公告）日：2013-10-10

  The invention discloses processes for preparing compounds comprising an α-amino acid motif. The compounds are useful in e.g. the chemical ligation of peptides.

  本发明公开了制备含有α-氨基酸基序列的化合物的方法。这些化合物可用于肽的化学连接等方面。
• Biodegradable polymer compositions
  申请人：NOVA PHARMACEUTICAL CORPORATION

  公开号：EP0483429A1

  公开（公告）日：1992-05-06

  Biodegradable polyanhydrides or polyester compositions based on amino acids. The compositions may be used as carriers for drugs or the like or as the drug source itself. The polymers are prepared from amino acids which are modified to include an additional carboxylic acid group.

  以氨基酸为基础的可生物降解的聚酐或聚酯组合物。这些组合物可用作药物或类似物质的载体，或用作药物来源本身。这些聚合物由氨基酸制备而成，氨基酸经过改性，包含一个额外的羧酸基团。
• Rates of Reduction of N-Chlorinated Peptides by Sulfite:  Relevance to Incomplete Dechlorination of Wastewaters
  作者：James S. Jensen、George R. Helz

  DOI：10.1021/es9707365

  日期：1998.2.1

  Biologically induced fragmentation of proteins during wastewater treatment produces peptides, which form long-lasting organic chloramines when the water is disinfected with Cl-2. To protect aquatic wildlife from residual chlorine, including chloramines, wastewaters are often treated with sulfur dioxide or sulfite salts. This strategy incompletely eliminates residual chlorine species. Here we report that dechlorination rate constants of N-chloropeptides are 1-2 order of magnitude smaller than those for NH2Cl and some aliphatic organic chloramines. Slow rates explain the prevalence of N-chloropeptides in dechlorinated wastewaters after faster reacting chlorine species have been eliminated. Dechlorination is subject to general acid catalysis. For N-chlorinated leucylalanine, the rate law above pH 6 in phosphate buffer at 25 degrees C and I approximate to 0.1 M is as follows: rate = (9.92 +/- 0.41 x 10(3)[H2PO4-] + 5.70 +/- 0.52 x 10(8)[H3O+] + 5.3 +/- 0.2)[SO32-][Cl-Leu-Ala] (concentrations in M, time in s). Rate constants for other peptides appear to be of similar magnitude; variations in the acid-catalyzed terms among different hydrophobic peptides correlate with solvation energies of side chains. The kinetic data suggest that reducing N-chloropeptides in wastewaters by 75% or more will require reaction times generally >0.5 h at environmentally acceptable S-IV doses and pH values.

表征谱图