{tert-butoxycarbonyl-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propyl]amino}acetic acid | 959513-40-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: {tert-butoxycarbonyl-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propyl]amino}acetic acid
• 英文别名: 2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetic acid
• CAS: 959513-40-7
• 化学式: C₂₅H₃₀N₂O₆
• 分子量: 454.523
• InChiKey: BIDVCBVRUMKTLV-INIZCTEOSA-N

物化性质

• 沸点：
  641.0±48.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {tert-butoxycarbonyl-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propyl]amino}acetic acid 、 Fmoc-L-苯丙氨酸 、 Boc-Gly-Ile-OH 、 (5R)-N^α-(fluoren-9-ylmethoxycarbonyl)-N^ε-benzyloxycarbonyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine 、 alkaline earth salt of/the/ methylsulfuric acid 以19.5 mg的产率得到
  参考文献：
  名称：

  Probing Molecular Interactions within Class II MHC A^q/Glycopeptide/T-Cell Receptor Complexes Associated with Collagen-Induced Arthritis

  摘要：

  T cells obtained in a mouse model for rheumatoid arthritis are activated by a glycopeptide fragment from rat type II collagen (CII) bound to the class II major histocompatibility complex A(q) molecule. We report a comparative model of A(q) in complex with the glycopeptide CII260-267. This model was used in a structure-based design approach where the amide bond between Ala(261) and Gly(262) in the glycopeptide was selected for replacement with psi[COCH2], psi[CH2NH2+], and psi[(E)-CH=CH] isosteres. Ala-Gly isostere building blocks were then synthesized and introduced in CII260-267 and CII259-273 glycopeptides. The modified glycopeptides were evaluated for binding to the A(q) molecule, and the results were interpreted in view of the A(q)/glycopeptide model. Moreover, recognition by a panel of T-cell hybridomas revealed high sensitivity for the backbone modifications. These studies contribute to the understanding of the interactions in the ternary A(q)/glycopeptide/T-cell receptor complexes that activate T cells in autoimmune arthritis and suggest possibilities for new vaccination approaches.

  DOI：

  10.1021/jm0705410
• 作为产物：
  描述：

  、 二碳酸二叔丁酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.92h， 以252 mg的产率得到{tert-butoxycarbonyl-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propyl]amino}acetic acid
  参考文献：
  名称：

  Probing Molecular Interactions within Class II MHC A^q/Glycopeptide/T-Cell Receptor Complexes Associated with Collagen-Induced Arthritis

  摘要：

  T cells obtained in a mouse model for rheumatoid arthritis are activated by a glycopeptide fragment from rat type II collagen (CII) bound to the class II major histocompatibility complex A(q) molecule. We report a comparative model of A(q) in complex with the glycopeptide CII260-267. This model was used in a structure-based design approach where the amide bond between Ala(261) and Gly(262) in the glycopeptide was selected for replacement with psi[COCH2], psi[CH2NH2+], and psi[(E)-CH=CH] isosteres. Ala-Gly isostere building blocks were then synthesized and introduced in CII260-267 and CII259-273 glycopeptides. The modified glycopeptides were evaluated for binding to the A(q) molecule, and the results were interpreted in view of the A(q)/glycopeptide model. Moreover, recognition by a panel of T-cell hybridomas revealed high sensitivity for the backbone modifications. These studies contribute to the understanding of the interactions in the ternary A(q)/glycopeptide/T-cell receptor complexes that activate T cells in autoimmune arthritis and suggest possibilities for new vaccination approaches.

  DOI：

  10.1021/jm0705410

文献信息

• Probing Molecular Interactions within Class II MHC A^q/Glycopeptide/T-Cell Receptor Complexes Associated with Collagen-Induced Arthritis
  作者：Ida E. Andersson、Balik Dzhambazov、Rikard Holmdahl、Anna Linusson、Jan Kihlberg

  DOI：10.1021/jm0705410

  日期：2007.11.1

  T cells obtained in a mouse model for rheumatoid arthritis are activated by a glycopeptide fragment from rat type II collagen (CII) bound to the class II major histocompatibility complex A(q) molecule. We report a comparative model of A(q) in complex with the glycopeptide CII260-267. This model was used in a structure-based design approach where the amide bond between Ala(261) and Gly(262) in the glycopeptide was selected for replacement with psi[COCH2], psi[CH2NH2+], and psi[(E)-CH=CH] isosteres. Ala-Gly isostere building blocks were then synthesized and introduced in CII260-267 and CII259-273 glycopeptides. The modified glycopeptides were evaluated for binding to the A(q) molecule, and the results were interpreted in view of the A(q)/glycopeptide model. Moreover, recognition by a panel of T-cell hybridomas revealed high sensitivity for the backbone modifications. These studies contribute to the understanding of the interactions in the ternary A(q)/glycopeptide/T-cell receptor complexes that activate T cells in autoimmune arthritis and suggest possibilities for new vaccination approaches.