N-t-butoxycarbonylglycyl-L-valylglycine | 96847-92-6

• 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: N-t-butoxycarbonylglycyl-L-valylglycine
• 英文别名: Boc-Gly-L-Val-Gly-OH；Boc-Gly-Val-Gly-OH；2-[[(2S)-3-methyl-2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]butanoyl]amino]acetic acid
• CAS: 96847-92-6
• 化学式: C₁₄H₂₅N₃O₆
• 分子量: 331.369
• InChiKey: VVNRTJYASXRDFE-NSHDSACASA-N

物化性质

• 沸点：
  629.1±50.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.15
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  133.83
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-t-butoxycarbonylglycyl-L-valylglycine 在 palladium on activated charcoal N-甲基吗啉 、 吡啶 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-Gly-Val-Gly-Leu-Pro-ONp
  参考文献：
  名称：

  弹性蛋白多五肽类似物的介电弛豫研究

  摘要：

  DOI：

  10.1021/j100313a053
• 作为产物：
  描述：

  Boc-G-V-G-OCH2Ph 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 生成 N-t-butoxycarbonylglycyl-L-valylglycine
  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。
• 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.
• 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：——
• Gowda, B.K. Kempe; Rangappa; Gowda, D. Channe, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 5, p. 1039 - 1044
  作者：Gowda, B.K. Kempe、Rangappa、Gowda, D. Channe

  DOI：——

  日期：——
• 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.