Boc-Trp-ΔAla-OMe | 957753-68-3

• 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-Trp-ΔAla-OMe
• 英文别名: Boc-Trp-Dha-OMe；methyl 2-[[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]prop-2-enoate
• CAS: 957753-68-3
• 化学式: C₂₀H₂₅N₃O₅
• 分子量: 387.436
• InChiKey: CKLCUHSBQASVAL-INIZCTEOSA-N

物化性质

• 熔点：
  78-80 °C
• 沸点：
  657.6±55.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-Trp-ΔAla-OMe 在 1-羟基苯并三唑 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Dehydrodipeptide Hydrogelators Containing Naproxen N-Capped Tryptophan: Self-Assembly, Hydrogel Characterization, and Evaluation as Potential Drug Nanocarriers

  摘要：

  在这项工作中，我们介绍了含有色氨酸、N端以非甾体抗炎药萘普生封端、C端为脱水氨基酸（脱水苯丙氨酸（ΔPhe）、脱水氨基丁酸（ΔAbu）和脱水丙氨酸（ΔAla））的二肽，这些二肽作为有效的蛋白酶抵抗型水凝胶形成剂。我们报告了最佳凝胶化条件。透射电子显微镜实验揭示，水凝胶由通过肽自组装形成的微/纳米尺寸纤维网络组成。荧光光谱和圆二色光谱表明，自组装过程是由芳香族基团的堆积相互作用驱动的。萘普生部分的萘环在纤维中通过手性堆积高度有序。流变学实验证明，最疏水的肽（含C端ΔPhe）在较低的临界凝胶化浓度下形成了更具弹性的凝胶。这种凝胶显示出不可逆的破碎，而C端ΔAbu和ΔAla凝胶虽然弹性较差，但表现出结构恢复和部分弹性性能的愈合。将一种潜在的抗肿瘤噻吩并[3,2-b]吡啶衍生物（非共价地）掺入含C端ΔPhe残基的凝胶形成剂形成的水凝胶中。荧光和福斯特共振能量转移测量表明，药物位于疏水环境中，靠近/与肽纤维相连，这表明这种类型的水凝胶是一个良好的药物纳米载体候选者。

  DOI：

  10.1021/acs.biomac.5b01006
• 作为产物：
  描述：

  t-butoxycarbonyl-L-tryptophyl-L-serine methyl ester 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 copper(l) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以55%的产率得到Boc-Trp-ΔAla-OMe
  参考文献：
  名称：

  Site-selective modification of peptides using rhodium and palladium catalysis: complementary electrophilic and nucleophilic arylation

  摘要：

  通过铑催化的共轭加成或钯催化的芳基胺化和醚化反应，实现了含有脱氢丙氨酸、酪氨酸和色氨酸残基的肽的选择性修饰。

  DOI：

  10.1039/b711533d

文献信息

• Site-selective modification of peptides using rhodium and palladium catalysis: complementary electrophilic and nucleophilic arylation
  作者：Christopher J. Chapman、Ai Matsuno、Christopher G. Frost、Michael C. Willis

  DOI：10.1039/b711533d

  日期：——

  The site-selective modification of peptides containing dehydroalanine, tyrosine and tryptophan residues has been achieved using rhodium catalysed conjugate additions or palladium catalysed aryl-amination and -etherification reactions.

  通过铑催化的共轭加成或钯催化的芳基胺化和醚化反应，实现了含有脱氢丙氨酸、酪氨酸和色氨酸残基的肽的选择性修饰。
• Non-classical <i>C</i>-saccharide linkage of dehydroalanine: synthesis of <i>C</i>-glycoamino acids and <i>C</i>-glycopeptides
  作者：Mengran Wang、Chao Wang、Xiuling Xie、Da Pan、Liangyu Liu、Qiao Chen、Zhixuan Li、Qi Zhang、Zhaoqing Xu

  DOI：10.1039/d2cc06653j

  日期：——

  Herein, a non-classical C-saccharide linkage is reported via a C5 radical of pentose or C6 radical of hexose addition to Michael acceptors. C(sp3)–S cleaved glycosyl thianthrenium salts are developed as the glycosyl radical agents. The reaction provides an efficient toolkit to synthesize β-glycosyl substituted unnatural amino acids as well as for the late-stage C-saccharide modification of peptides

  在此，通过向迈克尔受体添加戊糖的 C5 自由基或己糖的 C6 自由基，报道了非经典的C糖键。C(sp 3 )–S 裂解的糖基噻蒽盐被开发为糖基自由基试剂。该反应为合成 β-糖基取代的非天然氨基酸以及肽的后期C糖修饰提供了一个有效的工具包。
• Dehydrodipeptide Hydrogelators Containing Naproxen <i>N</i>-Capped Tryptophan: Self-Assembly, Hydrogel Characterization, and Evaluation as Potential Drug Nanocarriers
  作者：Helena Vilaça、Ana C. L. Hortelão、Elisabete M. S. Castanheira、Maria-João R. P. Queiroz、Loic Hilliou、Ian W. Hamley、José A. Martins、Paula M. T. Ferreira

  DOI：10.1021/acs.biomac.5b01006

  日期：2015.11.9

  In this work, we introduce dipeptides containing tryptophan N-capped with the nonsteroidal anti-inflammatory drug naproxen and C-terminal dehydroamino acids, dehydrophenylalanine (ΔPhe), dehydroaminobutyric acid (ΔAbu), and dehydroalanine (ΔAla) as efficacious protease resistant hydrogelators. Optimized conditions for gel formation are reported. Transmission electron microscopy experiments revealed that the hydrogels consist of networks of micro/nanosized fibers formed by peptide self-assembly. Fluorescence and circular dichroism spectroscopy indicate that the self-assembly process is driven by stacking interactions of the aromatic groups. The naphthalene groups of the naproxen moieties are highly organized in the fibers through chiral stacking. Rheological experiments demonstrated that the most hydrophobic peptide (containing C-terminal ΔPhe) formed more elastic gels at lower critical gelation concentrations. This gel revealed irreversible breakup, while the C-terminal ΔAbu and ΔAla gels, although less elastic, exhibited structural recovery and partial healing of the elastic properties. A potential antitumor thieno[3,2-b]pyridine derivative was incorporated (noncovalently) into the gel formed by the hydrogelator containing C-terminal ΔPhe residue. Fluorescence and Förster resonance energy transfer measurements indicate that the drug is located in a hydrophobic environment, near/associated with the peptide fibers, establishing this type of hydrogel as a good drug-nanocarrier candidate.

  在这项工作中，我们介绍了含有色氨酸、N端以非甾体抗炎药萘普生封端、C端为脱水氨基酸（脱水苯丙氨酸（ΔPhe）、脱水氨基丁酸（ΔAbu）和脱水丙氨酸（ΔAla））的二肽，这些二肽作为有效的蛋白酶抵抗型水凝胶形成剂。我们报告了最佳凝胶化条件。透射电子显微镜实验揭示，水凝胶由通过肽自组装形成的微/纳米尺寸纤维网络组成。荧光光谱和圆二色光谱表明，自组装过程是由芳香族基团的堆积相互作用驱动的。萘普生部分的萘环在纤维中通过手性堆积高度有序。流变学实验证明，最疏水的肽（含C端ΔPhe）在较低的临界凝胶化浓度下形成了更具弹性的凝胶。这种凝胶显示出不可逆的破碎，而C端ΔAbu和ΔAla凝胶虽然弹性较差，但表现出结构恢复和部分弹性性能的愈合。将一种潜在的抗肿瘤噻吩并[3,2-b]吡啶衍生物（非共价地）掺入含C端ΔPhe残基的凝胶形成剂形成的水凝胶中。荧光和福斯特共振能量转移测量表明，药物位于疏水环境中，靠近/与肽纤维相连，这表明这种类型的水凝胶是一个良好的药物纳米载体候选者。
• Peptide modification through site-selective residue interconversion: application of the rhodium-catalysed 1,4-addition of aryl siloxanes and boronates
  作者：Christopher J. Chapman、Jonathan D. Hargrave、Gerwyn Bish、Christopher G. Frost

  DOI：10.1016/j.tet.2008.07.067

  日期：2008.9

  The site-selective interconversion of serine and cysteine residues of di- and tripeptides into phenylalanine derivatives, bearing a range of functionalities, has been achieved in high yield and selectivity through the common dehydroalanine intermediate. Through the application and development of the rhodium-catalysed 1,4-addition to alpha,beta-dehydroamino acid moieties with organometallic nucleophiles, a variety of peptides have been successfully modified to contain unnatural amino acid residues in predesignated residue positions. (C) 2008 Elsevier Ltd. All rights reserved.