Boc-GFGFP-OH | 1270202-28-2

• 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-GFGFP-OH
• 英文别名: Boc-Gly-Phe-Gly-Phe-Pro-OH；(2S)-1-[(2S)-2-[[2-[[(2S)-2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]-3-phenylpropanoyl]amino]acetyl]amino]-3-phenylpropanoyl]pyrrolidine-2-carboxylic acid
• CAS: 1270202-28-2
• 化学式: C₃₂H₄₁N₅O₈
• 分子量: 623.706
• InChiKey: KBFKKLTZUMTKNC-SDHOMARFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  183
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Boc-GFGFP-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 (2S)-2-[(2-aminoacetyl)amino]-N-[2-[[(2S)-1-[(2S)-2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidine-1-carbonyl]pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]-3-phenylpropanamide;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：

  HPheGlyOBn 在 N-甲基吗啉 、 palladium 10% on activated carbon 、 甲酸铵 、 氯甲酸异丁酯 作用下， 生成 Boc-GFGFP-OH
  参考文献：
  名称：

  设计和合成含色氨酸的肽作为潜在的止痛药和消炎药。

  摘要：

  通过分析和光谱技术设计，合成和表征了一系列新的较小肽，这些肽在C端具有色氨酸，并且具有不同的N保护的氨基酸/肽。这些肽的镇痛和抗炎特性在体内进行分别以不同剂量和不同时间间隔使用甩尾法和角叉菜胶诱发的爪水肿法。合成的大多数肽都显示出增强的活性，特别是四肽和六肽29-31被发现比使用的参考标准品更有效。此外，某些肽甚至在给药24小时后仍显示出有希望的活性，而参考标准仅在3 h内才有活性。此外，这些化合物不具有任何致溃疡性。版权所有©2012欧洲肽协会和John Wiley＆Sons，Ltd.

  DOI：

  10.1002/psc.2431

文献信息

• 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。
• Design and synthesis of tryptophan containing peptides as potential analgesic and anti-inflammatory agents
  作者：R. Suhas、D. Channe Gowda

  DOI：10.1002/psc.2431

  日期：2012.8

  A new series of smaller peptides with tryptophan at C‐terminal and varying N‐protected amino acids/peptides were designed, synthesized and characterized by analytical and spectroscopic techniques. Analgesic and anti‐inflammatory properties of these peptides were carried out in vivo using tail‐flick method and carrageenan‐induced paw edema method, respectively, at different doses and different time

  通过分析和光谱技术设计，合成和表征了一系列新的较小肽，这些肽在C端具有色氨酸，并且具有不同的N保护的氨基酸/肽。这些肽的镇痛和抗炎特性在体内进行分别以不同剂量和不同时间间隔使用甩尾法和角叉菜胶诱发的爪水肿法。合成的大多数肽都显示出增强的活性，特别是四肽和六肽29-31被发现比使用的参考标准品更有效。此外，某些肽甚至在给药24小时后仍显示出有希望的活性，而参考标准仅在3 h内才有活性。此外，这些化合物不具有任何致溃疡性。版权所有©2012欧洲肽协会和John Wiley＆Sons，Ltd.
• 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.
• Structure-Based Rationale Design and Synthesis of Aurantiamide Acetate Analogues - Towards a New Class of Potent Analgesic and Anti-inflammatory Agents
  作者：Ramesh Suhas、Dase Channe Gowda

  DOI：10.1111/j.1747-0285.2012.01331.x

  日期：2012.5

  A series of new aurantiamide acetate analogues were synthesized by modifying its N‐terminal substitution and the amino acid residue. The structure of all these compounds was established on the basis of analytical and spectral studies. All the new derivatives were evaluated in vivo for their analgesic activity by tail flick method in mice and anti‐inflammatory activity against carrageenan‐induced oedema in albino rats at different doses (25, 50 and 100 mg/kg body weight). All the compounds exhibited significant pharmacological activity with no ulcerogenic liability. In particular, pentapeptides and tricosamers (30 amino acids) containing analogues have demonstrated high potency than the reference standards. These compounds hold promise for further development.