Boc-Gly-L-Phe-Gly-OH | 5500-90-3

• 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-L-Phe-Gly-OH
• 英文别名: Boc-Gly-Phe-Gly-OH；Boc-GFG-OH；2-[[(2S)-2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]-3-phenylpropanoyl]amino]acetic acid
• CAS: 5500-90-3
• 化学式: C₁₈H₂₅N₃O₆
• 分子量: 379.413
• InChiKey: MMOKAPLLHPBFHH-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Gly-L-Phe-Gly-OH 在 N-甲基吗啉 、 palladium 10% on activated carbon 、 甲酸铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 Boc-Gly-Phe-Gly-Phe-Pro-Trp-OMe
  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
• 作为产物：
  描述：

  Boc-Phe-Gly-OBzl 在 N-甲基吗啉 、 盐酸 、 palladium 10% on activated carbon 、 甲酸铵 、 氯甲酸异丁酯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 Boc-Gly-L-Phe-Gly-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

• Non-linear hydrophobic-induced pKa shifts: Implications for efficiency of conversion to chemical energy
  作者：Dan W. Urry、D. Channe Gowda、Shao Qing Peng、Timothy M. Parker

  DOI：10.1016/0009-2614(95)00442-7

  日期：1995.6

  Phe residues, a non-linear hydrophobic-induced pKa shift was observed with a ΔpKa of 0.4 (Asp) and 0.3 (Glu) on addition to 2 Phe residues per 30mer but with a ΔpKa of 4.7 (Asp) and 2.7 (Glu) on going from 4 Phe/30mer to 5 Phe/30mer. As a shift in pKa can be equivalent to the conversion to chemical energy from whatever energy input — mechanical, chemical, electrochemical, pressure or light — which effects

  通过在能够显示疏水折叠和组装过渡的聚三糖肽中每三十个残基使用一个ASP或一个Glu，并将五个Val残基中的一组（最接近ASP或Glu残基）逐步转变为疏水性更高的Phe残基，非线性疏水诱导的p ķ一个移位用观察到Δ p ķ一个上除了每30聚体，但用2个的Phe残基的0.4（ASP）和0.3（谷氨酸）Δ p ķ一个4.7（ASP）和2.7 （Glu）从4 Phe / 30mer升至5 Phe / 30mer。作为p K a的偏移可以等同于从任何能量输入（机械，化学，电化学，压力或光能）转化为化学能，这会影响疏水性的变化，非线性疏水诱导的p K a位移意味着能量转化的效率随着蛋白质基聚合物的疏水性。
• Drug complex
  申请人：Daiichi Pharmaceutical Co., Ltd.

  公开号：US20030171262A1

  公开（公告）日：2003-09-11

  A drug complex characterized in that a residue of a drug compound such as antineoplastic agents and a carboxy(C 1-4 )alkyldextran polyalcohol obtained by treating a dextran under conditions that enable substantially complete polyalcoholization are bound to each other by means of a spacer comprising an amino acid or a spacer comprising peptide-bonded 2 to 8 amino acids. Said complex is characterized in that it has excellent selectivity to tumorous sites so as to exhibit high antineoplastic activity and also achieves reduced appearance of toxicity.

  一种药物复合物，其特征在于将药物化合物（如抗肿瘤剂）的残留物和通过在使得多元醇化反应基本完全的条件下处理葡聚糖而获得的羧基（C1-4）烷基葡聚糖多元醇，通过含有氨基酸的间隔物或者由肽键连接的2至8个氨基酸组成的间隔物相互结合。该复合物的特点在于具有卓越的对肿瘤部位的选择性，从而表现出高度的抗肿瘤活性，并且能够实现毒性的减少。
• Drug complexes
  申请人：Daiichi Pharmaceutical Co., Ltd.

  公开号：US06436912B1

  公开（公告）日：2002-08-20

  A drug complex characterized in that a residue of a drug compound such as antineoplastic agents and a carboxy(C1-4)alkyldextran polyalcohol obtained by treating a dextran under conditions that enable substantially complete polyalcoholization are bound to each other by means of a spacer comprising an amino acid or a spacer comprising peptide-bonded 2 to 8 amino acids. Said complex is characterized-in that it has excellent selectivity to tumorous sites so as to exhibit high antineoplastic activity and also achieves reduced appearance of toxicity.

  一种药物复合物，其特征在于将药物化合物（如抗肿瘤药物）的残留物和通过在能够实现基本完全多元醇化的条件下处理葡聚糖而获得的羧基（C1-4）烷基葡聚糖多元醇通过含有氨基酸的间隔物或含有肽键的2至8个氨基酸的间隔物相互结合。该复合物的特征在于具有优异的肿瘤位点选择性，从而表现出高抗肿瘤活性，并实现毒性的降低。
• Process for producing drug complexes
  申请人：Daiichi Pharmaceutical Co., Ltd.

  公开号：US06291671B1

  公开（公告）日：2001-09-18

  A method for preparing a drug complex in which a polysaccharide derivative having carboxyl groups and a residue of a drug compound are bound to each other by means of a spacer comprising an amino acid or a spacer comprising peptide-bonded 2 to 8 amino acids, or a drug complex in which a polysaccharide derivative having carboxyl groups and a residue of a drug compound are bound to each other without the spacer, characterized in that an organic amine salt of the polysaccharide derivative having carboxyl groups is reacted with the drug compound or the spacer bound to the drug compound in a non-aqueous system. The reaction between the polysaccharide derivative having carboxyl groups and the drug compound bound with the spacer or the like can be carried out in high yields, and when a drug compound having a lactone ring is subjected to the reaction, side reactions can be reduced.

  一种制备药物复合物的方法，其中通过含有羧基的多糖衍生物和药物化合物残基之间的间隔物，该间隔物包括氨基酸或由肽键连接的2至8个氨基酸的间隔物，或者在没有间隔物的情况下将含有羧基的多糖衍生物和药物化合物残基结合在一起，其特征在于，将含有羧基的多糖衍生物的有机胺盐与药物化合物或与药物化合物结合的间隔物在非水系统中反应。含有羧基的多糖衍生物和与间隔物结合的药物化合物之间的反应可以高产率地进行，当药物化合物具有内酯环时，副反应可以被减少。
• 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.