Boc-Gly-Gly-Ala-Pro-OH | 151396-21-3

• 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-Gly-Gly-Ala-Pro-OH
• 英文别名: Boc-GGAP-OH；(2S)-1-[(2S)-2-[[2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]acetyl]amino]propanoyl]pyrrolidine-2-carboxylic acid
• CAS: 151396-21-3
• 化学式: C₁₇H₂₈N₄O₇
• 分子量: 400.432
• InChiKey: VYAWVXZFZLWEDU-QWRGUYRKSA-N

物化性质

• 沸点：
  755.3±60.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  154
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-Gly-Gly-Ala-Pro-OH 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.84h， 生成 2-amino-N-[2-[[(2S)-1-[(2S)-2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidine-1-carbonyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-2-oxoethyl]acetamide;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  Synthesis of elastin based peptides conjugated to benzisoxazole as a new class of potent antimicrobials – A novel approach to enhance biocompatibility

  摘要：

  The peptides of elastin sequences chosen for the present study included tetrapeptides, pentapeptides and tricosapeptides (30 amino acids), synthesized by classical solution phase method and conjugated to [3-(4-piperidyl)-6-fluoro-1,2-benzisoxazole]. The structures of the compounds were confirmed by physical and spectroscopic techniques followed by the antimicrobial evaluation by both agar well diffusion and microdilution methods. Here we wish to report the effect of conjugation of these moieties which enabled us to identify a novel set of peptides conjugated to heterocycle which have exhibited more potent antimicrobial activity than the conventional drugs used. Further, conjugates of tricosamers 34 and 35 were able to inhibit the growth of fungal species at 3-5 mu g/mL which is nearly 5 fold more potent than the reference drug. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.005
• 作为产物：
  描述：

  Boc-Gly-Gly-Ala-Pro-OBzl 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 Boc-Gly-Gly-Ala-Pro-OH
  参考文献：
  名称：

  A New Family of Highly Potent Inhibitors of Microbes: Synthesis and Conjugation of Elastin Based Peptides to Piperazine Derivative

  摘要：

  基于弹性蛋白（一种哺乳动物弹性蛋白）重复序列的弹性蛋白聚合物，所选择的弹性蛋白肽序列包括四肽、五肽和三十二肽（30个氨基酸），以及芳香族氨基酸。这些序列被偶联到1-(2,3-二氯苯基)哌嗪，以研究偶联对其活性的影响。所得偶联物通过物理和分析技术进行表征，随后进行抗菌评估。研究表明，所有偶联物的活性均比传统药物有所提高。此外，三十二肽的偶联物对真菌物种显示出非凡的活性，其最低抑菌浓度（MIC）值为3-5 μg/ml，比所用抗生素强五倍。

  DOI：

  10.1007/s10989-011-9282-8

文献信息

• Hydrophobicity dependence of oxidation of tetrapeptides of elastin sequences with Mn(III): Synthesis, characterization, kinetics, and mechanistic study
  作者：B. K. Kempe Gowda、H. S. Prasad、K. S. Rangappa、D. Channe Gowda

  DOI：10.1002/kin.10015

  日期：2002.1

  The analogues of elastin sequences, glycyl-glycyl-alanyl-proline (GGAP), glycyl-glycyl-phenylalanyl-proline (GGFP), and glycyl-glycyl-isoleucyl-proline (GGIP) were synthesized by classical solution phase method and characterized. The kinetics of oxidation of these tetrapeptides (TETP) by Mn(III) has been studied in the presence of sulphate ions in acidic solution at 25°C. The reaction was followed

  弹性蛋白序列的类似物，甘氨酰-甘氨酰-丙氨酰-脯氨酸(GGAP)、甘氨酰-甘氨酰-苯丙氨酰-脯氨酸(GGFP)和甘氨酰-甘氨酰-异亮氨酰-脯氨酸(GGIP)通过经典液相法合成并表征。在 25°C 酸性溶液中存在硫酸根离子的情况下，研究了 Mn(III) 对这些四肽 (TETP) 的氧化动力学。在 λmax = 500 nm 处用分光光度法跟踪反应。观察到速率对 [Mn(III)] 和 [TETP] 的一级依赖性。该速率与还原产物、Mn(II) 和氢离子的浓度无关。研究了改变介质介电常数和添加阴离子（如硫酸盐、氯化物或高氯酸盐）的影响。激活参数已使用 Arrhenius 和 Erying 图进行了评估。氧化产物被分离和表征。提出了在限速步骤中涉及 TETP 与 Mn(III) 反应的机制。在这些序列的氧化速率和疏水性之间注意到明显的相关性，其中增加的疏水性导致增加的氧化速率。© 2001 John
• Elastomeric polypeptide matrices for preventing adhesion of biological
  申请人：The UAB Research Foundation

  公开号：US05519004A1

  公开（公告）日：1996-05-21

  The invention provides a bioelastomer comprising tetrapeptide and/or pentapeptide monomeric units of the formula: R.sub.1 PGR.sub.2 G.sub.n wherein R.sub.1 is a peptide-producing residue of alanine or glycine; P is a peptide-producing residue of proline; G is a peptide-producing residue of glycine; R.sub.2 is a peptide-producing residue of glycine or alanine; and n is 0 or 1. In a further aspect of the invention, a method is provided for preventing adhesion of biological materials, such as protein, cells, and tissues, by forming a protective layer between a first surface and a second surface using the bioelastomer.

  本发明提供了一种生物弹性体，其包括以下式子的四肽和/或五肽单体单位：R.sub.1 PGR.sub.2 G.sub.n，其中R.sub.1是丙氨酸或甘氨酸的肽产生残基；P是脯氨酸的肽产生残基；G是甘氨酸的肽产生残基；R.sub.2是甘氨酸或丙氨酸的肽产生残基；n为0或1。本发明还提供了一种方法，通过使用生物弹性体在第一表面和第二表面之间形成保护层，以防止生物材料（如蛋白质、细胞和组织）的粘附。
• Synthesis of elastin based peptides conjugated to benzisoxazole as a new class of potent antimicrobials – A novel approach to enhance biocompatibility
  作者：R. Suhas、S. Chandrashekar、D. Channe Gowda

  DOI：10.1016/j.ejmech.2010.12.005

  日期：2011.2

  The peptides of elastin sequences chosen for the present study included tetrapeptides, pentapeptides and tricosapeptides (30 amino acids), synthesized by classical solution phase method and conjugated to [3-(4-piperidyl)-6-fluoro-1,2-benzisoxazole]. The structures of the compounds were confirmed by physical and spectroscopic techniques followed by the antimicrobial evaluation by both agar well diffusion and microdilution methods. Here we wish to report the effect of conjugation of these moieties which enabled us to identify a novel set of peptides conjugated to heterocycle which have exhibited more potent antimicrobial activity than the conventional drugs used. Further, conjugates of tricosamers 34 and 35 were able to inhibit the growth of fungal species at 3-5 mu g/mL which is nearly 5 fold more potent than the reference drug. (C) 2010 Elsevier Masson SAS. All rights reserved.
• A New Family of Highly Potent Inhibitors of Microbes: Synthesis and Conjugation of Elastin Based Peptides to Piperazine Derivative
  作者：R. Suhas、S. Chandrashekar、D. Channe Gowda

  DOI：10.1007/s10989-011-9282-8

  日期：2012.6

  Elastin protein-based polymers have their origin in repeating sequences of the mammalian elastic protein, elastin. The sequences of elastin peptides chosen are tetrapeptides, pentapeptides and tricosamers (30 amino acids) and also aromatic amino acids. These have been conjugated to 1-(2,3-dichlorophenyl)piperazine to study the effect of conjugation on the activity. The conjugates so obtained were characterized by physical and analytical techniques followed by the antimicrobial evaluation. The study revealed that all the conjugates have exhibited enhanced activity than the conventional drugs. Further, the conjugates of tricosamers have shown extraordinary activity against the fungal species with MIC value of 3–5 μg/ml which is five fold more potent than the antibiotic used.

  基于弹性蛋白（一种哺乳动物弹性蛋白）重复序列的弹性蛋白聚合物，所选择的弹性蛋白肽序列包括四肽、五肽和三十二肽（30个氨基酸），以及芳香族氨基酸。这些序列被偶联到1-(2,3-二氯苯基)哌嗪，以研究偶联对其活性的影响。所得偶联物通过物理和分析技术进行表征，随后进行抗菌评估。研究表明，所有偶联物的活性均比传统药物有所提高。此外，三十二肽的偶联物对真菌物种显示出非凡的活性，其最低抑菌浓度（MIC）值为3-5 μg/ml，比所用抗生素强五倍。