(5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxohexanoic acid | 959513-38-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxohexanoic acid
• CAS: 959513-38-3
• 化学式: C₂₁H₂₁NO₅
• 分子量: 367.401
• InChiKey: UDCSIKPTJTVTQZ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxohexanoic 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7 mg的产率得到(4S)-4-[[2-[[(2S,5R)-6-amino-2-[[(2S)-2-[[(5S)-5-[[(2S,3S)-2-[(2-aminoacetyl)amino]-3-methylpentanoyl]amino]-4-oxohexanoyl]amino]-3-phenylpropanoyl]amino]-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoyl]amino]acetyl]amino]-5-[[(2S)-5-amino-1-[[2-[(2S)-2-[[(2S)-6-amino-1-[[2-[[(2S)-4-carboxy-1-[[(1S,2R)-1-carboxy-2-hydroxypropyl]amino]-1-oxobutan-2-yl]amino]-2-oxoethyl]amino]-1-oxohexan-2-yl]carbamoyl]pyrrolidin-1-yl]-2-oxoethyl]amino]-1,5-dioxopentan-2-yl]amino]-5-oxopentanoic 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
• 作为产物：
  描述：

  、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 4.5h， 以110 mg的产率得到(5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxohexanoic 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.