βALA-NH-(CH2)2-(CH2-C6H4-NO2)G-(3-aminomethylbenzoic acid)-LTV

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: βALA-NH-(CH2)2-(CH2-C6H4-NO2)G-(3-aminomethylbenzoic acid)-LTV
• 英文别名: (2S)-2-[[(2S,3R)-2-[[(2S)-2-[[3-[[[2-[2-[[(2S)-2-[[(2S)-2-(3-aminopropanoylamino)-4-methylpentanoyl]amino]propanoyl]amino]ethyl-[(4-nitrophenyl)methyl]amino]acetyl]amino]methyl]benzoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-methylbutanoic acid
• 化学式: C₄₆H₇₀N₁₀O₁₂
• 分子量: 955.122
• InChiKey: VNOPNXLVCYSIPQ-WGIMCKAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  68
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  336
• 氢给体数：
  10
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  Fmoc-L-缬氨酸 、 Fmoc-L-亮氨酸 、 Fmoc-L-丙氨酸 、 FMOC-beta-丙氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 以48%的产率得到βALA-NH-(CH2)2-(CH2-C6H4-NO2)G-(3-aminomethylbenzoic acid)-LTV
  参考文献：
  名称：

  Synthetic Anticancer Vaccine Candidates:  Rational Design of Antigenic Peptide Mimetics That Activate Tumor-Specific T-Cells

  摘要：

  A rational design approach was followed to develop peptidomimetic analogues of a cytotoxic T-cell epitope capable of stimulating T-cell responses as strong as or stronger (heteroclytic) than those of parental antigenic peptides. The work described herein focused on structural alterations of the central amino acids of the melanoma tumor-associated antigenic peptide Melan-A/MART-1(26-35) using nonpeptidic units. A screening was first realized in silico to select altered peptides potentially capable of fitting at the interface between the major histocompatibilty complex (MHC) class-I HLA-A2 molecule and T-cell receptors (TCRs). Two compounds appeared to be high-affinity ligands to the HLA-A2 molecule and stimulated several Melan-A/MART-1 specific T-cell clones. Most remarkably, one of them even managed to amplify the response of one clone. Together, these results indicate that central TCR-contact residues of antigenic peptides can be replaced by nonpeptidic motifs without loss of binding affinity to MHC class-I molecules and T-cell triggering capacity.

  DOI：

  10.1021/jm0613368

文献信息

• Synthetic Anticancer Vaccine Candidates:  Rational Design of Antigenic Peptide Mimetics That Activate Tumor-Specific T-Cells
  作者：Céline Douat-Casassus、Nathalie Marchand-Geneste、Elisabeth Diez、Nadine Gervois、Francine Jotereau、Stéphane Quideau

  DOI：10.1021/jm0613368

  日期：2007.4.1

  A rational design approach was followed to develop peptidomimetic analogues of a cytotoxic T-cell epitope capable of stimulating T-cell responses as strong as or stronger (heteroclytic) than those of parental antigenic peptides. The work described herein focused on structural alterations of the central amino acids of the melanoma tumor-associated antigenic peptide Melan-A/MART-1(26-35) using nonpeptidic units. A screening was first realized in silico to select altered peptides potentially capable of fitting at the interface between the major histocompatibilty complex (MHC) class-I HLA-A2 molecule and T-cell receptors (TCRs). Two compounds appeared to be high-affinity ligands to the HLA-A2 molecule and stimulated several Melan-A/MART-1 specific T-cell clones. Most remarkably, one of them even managed to amplify the response of one clone. Together, these results indicate that central TCR-contact residues of antigenic peptides can be replaced by nonpeptidic motifs without loss of binding affinity to MHC class-I molecules and T-cell triggering capacity.