3-[6-(2-benzyloxycarbonylamino-ethyl)-8-(2-tert-butoxycarbonyl-vinyl)-4-(2-ethoxycarbonyl-ethyl)-dibenzofuran-2-yl]-acrylic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-[6-(2-benzyloxycarbonylamino-ethyl)-8-(2-tert-butoxycarbonyl-vinyl)-4-(2-ethoxycarbonyl-ethyl)-dibenzofuran-2-yl]-acrylic acid tert-butyl ester
• 英文别名: ethyl 3-[2,8-bis[(E)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]-6-[2-(phenylmethoxycarbonylamino)ethyl]dibenzofuran-4-yl]propanoate
• 化学式: C₄₁H₄₇NO₉
• 分子量: 697.825
• InChiKey: XZGGNVYVPVWWAY-CJQREAPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  51
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 3-[6-(2-benzyloxycarbonylamino-ethyl)-8-(2-tert-butoxycarbonyl-vinyl)-4-(2-ethoxycarbonyl-ethyl)-dibenzofuran-2-yl]-acrylic acid tert-butyl ester 在 10percent Pd/C lithium hydroxide 、 水 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 24.0h， 以95%的产率得到3-{2,8-bis(2-tert-butoxycarbonyl-ethyl)-6-[2-(9H-fluoren-9-yl-methoxycarbonylamino)-ethyl]-dibenzofuran-4-yl}-propionic acid
  参考文献：
  名称：

  Synthesis of a Negatively Charged Dibenzofuran-Based β-Turn Mimetic and Its Incorporation into the WW Miniprotein-Enhanced Solubility without a Loss of Thermodynamic Stability

  摘要：

  A versatile synthesis has been developed to functionalize the 4-(2-aminoethyl)-6-dibenzofuran propionic acid residue (1a) at the 2 and 8 positions with a variety of different substructures, The unfunctionalized version of this peptidomimetic (1a) is known to facilitate beta-hairpin formation in a variety of small peptides and proteins in aqueous solution when incorporated in place of the i + 1 and i + 2 residues of a U-turn. In this study, we append propionate substituents on 1 a at the 2 and 8 positions to successfully overcome solubility problems encountered with the incorporation of la in place of the i + 1 and i + 2 residues of the beta-turn in loop 1 of the WW domain. The thermodynamic stability of several WW domain analogues incorporating residues 1a and 1b was compared to that of the wild-type sequence revealing comparable DeltaG(H2O) unfolding values at 4 degreesC ranging from 3 to 3.6 kcal/mol. WW domains incorporating residue 1b exhibit improved solubility (exceeding 100 muM) and resistance to aggregation without compromising thermodynamic stability.

  DOI：

  10.1021/ja020675x
• 作为产物：
  描述：

  二苯并呋喃 在 10percent Pd/C palladium diacetate 、 四甲基乙二胺 、 硫酸 、 二苯基磷酸 、 氢气 、 碘 、 叔丁基锂 、 仲丁基锂 、 一氯化碘 、 碘酸 、 potassium carbonate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醚 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， -78.0~80.0 ℃ 、344.75 kPa 条件下， 反应 126.17h， 生成 3-[6-(2-benzyloxycarbonylamino-ethyl)-8-(2-tert-butoxycarbonyl-vinyl)-4-(2-ethoxycarbonyl-ethyl)-dibenzofuran-2-yl]-acrylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of a Negatively Charged Dibenzofuran-Based β-Turn Mimetic and Its Incorporation into the WW Miniprotein-Enhanced Solubility without a Loss of Thermodynamic Stability

  摘要：

  A versatile synthesis has been developed to functionalize the 4-(2-aminoethyl)-6-dibenzofuran propionic acid residue (1a) at the 2 and 8 positions with a variety of different substructures, The unfunctionalized version of this peptidomimetic (1a) is known to facilitate beta-hairpin formation in a variety of small peptides and proteins in aqueous solution when incorporated in place of the i + 1 and i + 2 residues of a U-turn. In this study, we append propionate substituents on 1 a at the 2 and 8 positions to successfully overcome solubility problems encountered with the incorporation of la in place of the i + 1 and i + 2 residues of the beta-turn in loop 1 of the WW domain. The thermodynamic stability of several WW domain analogues incorporating residues 1a and 1b was compared to that of the wild-type sequence revealing comparable DeltaG(H2O) unfolding values at 4 degreesC ranging from 3 to 3.6 kcal/mol. WW domains incorporating residue 1b exhibit improved solubility (exceeding 100 muM) and resistance to aggregation without compromising thermodynamic stability.

  DOI：

  10.1021/ja020675x

文献信息

• Synthesis of a Negatively Charged Dibenzofuran-Based β-Turn Mimetic and Its Incorporation into the WW Miniprotein-Enhanced Solubility without a Loss of Thermodynamic Stability
  作者：Ramesh Kaul、Songpon Deechongkit、Jeffery W. Kelly

  DOI：10.1021/ja020675x

  日期：2002.10.1

  A versatile synthesis has been developed to functionalize the 4-(2-aminoethyl)-6-dibenzofuran propionic acid residue (1a) at the 2 and 8 positions with a variety of different substructures, The unfunctionalized version of this peptidomimetic (1a) is known to facilitate beta-hairpin formation in a variety of small peptides and proteins in aqueous solution when incorporated in place of the i + 1 and i + 2 residues of a U-turn. In this study, we append propionate substituents on 1 a at the 2 and 8 positions to successfully overcome solubility problems encountered with the incorporation of la in place of the i + 1 and i + 2 residues of the beta-turn in loop 1 of the WW domain. The thermodynamic stability of several WW domain analogues incorporating residues 1a and 1b was compared to that of the wild-type sequence revealing comparable DeltaG(H2O) unfolding values at 4 degreesC ranging from 3 to 3.6 kcal/mol. WW domains incorporating residue 1b exhibit improved solubility (exceeding 100 muM) and resistance to aggregation without compromising thermodynamic stability.