Boc-L-Ala-L-Ala-L-Ala-OBzl | 18671-06-2

• 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: Boc-L-Ala-L-Ala-L-Ala-OBzl
• 英文别名: N-t-butoxycarbonyl-L-alanyl-L-alanyl-L-alanine benzyl ester；Boc-Ala-Ala-Ala-OBzl；(N-Boc-Ala)-Ala-Ala-benzylester；Boc-A-A-A-OCH2Ph；Boc-Ala-Ala-Ala-OBn；benzyl (2S)-2-[[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoyl]amino]propanoate
• CAS: 18671-06-2
• 化学式: C₂₁H₃₁N₃O₆
• 分子量: 421.494
• InChiKey: IRBADJFKHSPLPA-KKUMJFAQSA-N

物化性质

• 沸点：
  633.7±50.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-L-Ala-L-Ala-L-Ala-OBzl 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以77%的产率得到H-L-Ala-L-Ala-L-Ala-OBzl.HCl
  参考文献：
  名称：

  Synthesis and antibacterial activities of theanine-containing oligopeptides.

  摘要：

  茶氨酸是 L-谷氨酸的一种抗代谢物，是一种弱抗菌剂。为了获得具有更强生物活性的茶氨酸衍生物，我们制备了一系列茶氨酸-L-丙氨酸寡肽 H-Tea-L-Alan-OH（n=1、2、3），以及这些肽在氨基端和/或羧基端带有阻断基团的几种衍生物，并研究了它们的抗菌和抗谷氨酸脱羧酶活性。丙氨酰-L-丙氨酸和丙氨酰-L-丙氨酰-L-丙氨酸对金黄色葡萄球菌和大肠杆菌的抑制作用最强，对金黄色葡萄球菌的抑制率是丙氨酸的 2 至 23 倍，对大肠杆菌的抑制率是丙氨酸的 3 至 4 倍。肽末端基团的结构修饰，尤其是 N-酰化，会明显降低抗菌活性。即使在 50 μmol/ml 的浓度下，也没有任何一种茶氨酸和茶氨酸-L-丙氨酸寡肽具有明显的抑制细菌谷氨酸脱羧酶的能力。

  DOI：

  10.1248/cpb.28.3549
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-L-alanyl-L-alanine benzyl ester 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 Boc-L-Ala-L-Ala-L-Ala-OBzl
  参考文献：
  名称：

  Thermal Synthesis of Polypeptides from N-t-Butyloxycarbonyltripeptide Derivatives without Reactive Side Chains

  摘要：

  已知 N-叔丁氧羰基-天冬氨酸（Boc-Asp-OH）和一些肽的 N-叔丁氧羰基衍生物的热反应，其中 C 端是天冬氨酸残基，作为 Boc-Gly-Gly-L-Asp-OH 的反应残基。C- 末端的两个羧基被认为可以形成酸酐或直接生成肽键。本研究报告了 N-叔丁氧羰基三肽衍生物（如 Boc-Pro-Pro-Gly-OH、Boc-Pro-Pro-Gly-NH2、Boc-Pro-Gly-OCH3 和 Boc-Ala- Ala-Ala-OH）与 C 端羧基的热反应。在接近熔点的恒温条件下进行 1 至 24 小时的热反应，可得到平均分子量达到 2,500 Da 的多肽。

  DOI：

  10.14233/ajchem.2023.29585

文献信息

• Development of Supramolecular Organo-Gel Based on Tripeptide Skeletons
  作者：Eriko Azuma、Kouji Kuramochi、Kazunori Tsubaki

  DOI：10.1248/cpb.58.680

  日期：——

  Boc-Ser-Val-Gly-OCH2Ph (31) showed high gelation abilities in the aromatic solvents, particularly in toluene. The minimum gelation concentration of 31 in toluene was 10 mg/ml, suggesting that 2500 molecules of toluene were immobilized by each molecule of the tripeptide 31. The FT-IR data indicated that formation of antiparallel β-sheets through intermolecular hydrogen bonding was central to the generation of nanofibers during gelation.

  Boc-Ser-Val-Gly-OCH2Ph (31) 在芳香族溶剂中显示出强大的成胶能力，尤其是在甲苯中。31在甲苯中的最低成胶浓度为10 mg/ml，这意味着每分子三肽31固定了2500个甲苯分子。傅里叶变换红外光谱数据显示，通过分子间氢键形成反平行β-折叠是成胶过程中产生纳米纤维的关键。
• Synthesis and antibacterial activities of theanine-containing oligopeptides.
  作者：YASUO ODA、HIROKO TAGUCHI、NOBUTAKA MASAOKA、KAZUO MINAMI、SUSUMU HONDA、KOZO OKADA

  DOI：10.1248/cpb.28.3549

  日期：——

  Theanine, an antimetabolite of L-glutamic acid, is a weak antibacterial agent. In the hope of obtaining theanine derivatives which have more potent biological activities, a series of theanyl-L-alanine oligopeptides, H-Tea-L-Alan-OH (n=1, 2, 3), and several derivatives of these peptides with blocking groups at the amono-and/or carboxyl-termini were prepared, and their antibacterial and anti-glutamic decarboxylase activities were examined. Theanyl-L-alanine and theanyl-L-alanyl-L-alanine inhibited the growth of Staphylococcus aureus and Escherichia coli most strongly, the percent inhibitions being 2 to 23 times higher against S. aureus or 3 to 4 times higher against E. coli than those of theanine. Structural modifications at the end groups of the peptides, especially N-acylation, caused marked reductions in the antibacterial activities. None of the theanine and theanyl-L-alanine oligopeptides possessed any significant ability to inhibit bacterial glutamic decarboxylase even at a concentration of 50 μmol/ml.

  茶氨酸是 L-谷氨酸的一种抗代谢物，是一种弱抗菌剂。为了获得具有更强生物活性的茶氨酸衍生物，我们制备了一系列茶氨酸-L-丙氨酸寡肽 H-Tea-L-Alan-OH（n=1、2、3），以及这些肽在氨基端和/或羧基端带有阻断基团的几种衍生物，并研究了它们的抗菌和抗谷氨酸脱羧酶活性。丙氨酰-L-丙氨酸和丙氨酰-L-丙氨酰-L-丙氨酸对金黄色葡萄球菌和大肠杆菌的抑制作用最强，对金黄色葡萄球菌的抑制率是丙氨酸的 2 至 23 倍，对大肠杆菌的抑制率是丙氨酸的 3 至 4 倍。肽末端基团的结构修饰，尤其是 N-酰化，会明显降低抗菌活性。即使在 50 μmol/ml 的浓度下，也没有任何一种茶氨酸和茶氨酸-L-丙氨酸寡肽具有明显的抑制细菌谷氨酸脱羧酶的能力。
• Dutta, Anand S.; Giles, Michael B.; Williams, Joseph C., Journal of the Chemical Society. Perkin transactions I, 1986, p. 1655 - 1664
  作者：Dutta, Anand S.、Giles, Michael B.、Williams, Joseph C.

  DOI：——

  日期：——
• Design, synthesis and inhibition activity of novel cyclic peptides against protein tyrosine phosphatase A from Mycobacterium tuberculosis
  作者：Koushik Chandra、Debajyoti Dutta、Amit K. Das、Amit Basak

  DOI：10.1016/j.bmc.2010.09.052

  日期：2010.12

  Mycobacterium tuberculosis, the causative agent for tuberculosis has employed several signalling molecules to sense the host cellular environment and act accordingly. For example, protein tyrosine phosphatase A (MPtpA) of M. tuberculosis, a signalling protein belonging to the tyrosine phosphatase superfamily, is involved in phagocytosis and is active in virulent mycobacterial form. Starting from a beta-lactam framework a new class of structure based cyclic peptide (CP) inhibitors was designed. The synthesis involves a crucial intramolecular transamidation via a ring opening reaction. All the compounds show moderate to good inhibitory activities against MPtpA in micromolar concentrations. The results of inhibition kinetics suggest mixed mode of inhibition. The binding constant determined from circular dichroism (CD) and fluorescence quenching studies shows strong binding of the hydrophilic side chain of CPs with the enzyme active site residues. All these are well supported by docking studies. (C) 2010 Elsevier Ltd. All rights reserved.
• Peptide derivatives specific for a Plasmodium falciparum proteinase inhibit the human erythrocyte invasion by merozoites
  作者：Roger Mayer、Isabelle Picard、Philippe Lawton、Philippe Grellier、Christine Barrault、Michel Monsigny、Joseph Schrevel

  DOI：10.1021/jm00114a011

  日期：1991.10

  A specific proteinase of P. falciparum merozoites has been detected by using hydrosoluble fluorogenic peptidic substrates synthesized by classical peptide chemistry; their N-terminal end was acylated by a gluconoyl group that protects them from aminopeptidase degradation and increases their hydrosolubility, and their carboxylic end was substituted by a 3-amino-9-ethylcarbazole group. The sequence Val-Leu-Gly-Lys was found to be the most specific substrate. On this basis, reversible peptidic inhibitors were synthesized by substituting the C-terminal lysyl residue, at the proteolytic site, by different alkylamines and amino alcohols. The activity of these compounds, studied on the P. falciparum proteinase and in in vitro cultures, strongly suggests a specific effect of this peptidic sequence on the reinvasion process. The peptidic inhibitors do not impair the release of merozoites from schizonts, but selectively inhibit the invasion step leading to the formation of rings. Although the natural target of this enzyme is not yet known, these specific peptide inhibitors could lead to a new antimalarial approach.