methyl (2S)-2-[(3S,4R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxy-2-oxopyrrolidin-1-yl]-3-(1H-indol-3-yl)propanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: methyl (2S)-2-[(3S,4R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxy-2-oxopyrrolidin-1-yl]-3-(1H-indol-3-yl)propanoate
• 化学式: C₂₇H₄₇N₆O₈Pol
• 分子量: 539.6
• InChiKey: CZEIACPJNOHGDN-IARZGTGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[(3S,4R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxy-2-oxopyrrolidin-1-yl]-3-(1H-indol-3-yl)propanoate 在 苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 5-羟基-1,3-苯并噻唑-2(3H)-硫酮
  参考文献：
  名称：

  α-Amino-β-hydroxy-γ-lactam for Constraining Peptide Ser and Thr Residue Conformation

  摘要：

  alpha-Amino-beta-hydroxy-gamma-lactam 1 is a peptide mimic in which the Ser/Thr residue omega-, psi-, and chi-dihedral angle geometry all are constrained by the 5-membered lactam ring. Lactams 1 were made by employing N-(Fmoc)oxiranylglycine 3 as a bis-electrophile in TFE with cat. BzOH to sequentially alkylate and acylate a variety of amino acid derivatives in one pot. Solid-phase synthesis of beta-hydroxy-gamma-lactam 8, an analogue of the IL-1 modulator 101.10, was achieved using this method for studying Ser/Thr geometry.

  DOI：

  10.1021/ol1000582
• 作为产物：
  描述：

  [9-fluorenylmethoxycarbonyl]-2-vinylglycine methyl ester 、 L-tryptophan 在 间氯过氧苯甲酸 、 2,2,2-三氟乙醇 、 苯甲酸 作用下， 以 1,2-二氯乙烷 、 二氯甲烷 为溶剂， 以84%的产率得到methyl (2S)-2-[(3S,4R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxy-2-oxopyrrolidin-1-yl]-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  α-Amino-β-hydroxy-γ-lactam for Constraining Peptide Ser and Thr Residue Conformation

  摘要：

  alpha-Amino-beta-hydroxy-gamma-lactam 1 is a peptide mimic in which the Ser/Thr residue omega-, psi-, and chi-dihedral angle geometry all are constrained by the 5-membered lactam ring. Lactams 1 were made by employing N-(Fmoc)oxiranylglycine 3 as a bis-electrophile in TFE with cat. BzOH to sequentially alkylate and acylate a variety of amino acid derivatives in one pot. Solid-phase synthesis of beta-hydroxy-gamma-lactam 8, an analogue of the IL-1 modulator 101.10, was achieved using this method for studying Ser/Thr geometry.

  DOI：

  10.1021/ol1000582

文献信息

• α-Amino-β-hydroxy-γ-lactam for Constraining Peptide Ser and Thr Residue Conformation
  作者：Daniel J. St-Cyr、Andrew G. Jamieson、William D. Lubell

  DOI：10.1021/ol1000582

  日期：2010.4.16

  alpha-Amino-beta-hydroxy-gamma-lactam 1 is a peptide mimic in which the Ser/Thr residue omega-, psi-, and chi-dihedral angle geometry all are constrained by the 5-membered lactam ring. Lactams 1 were made by employing N-(Fmoc)oxiranylglycine 3 as a bis-electrophile in TFE with cat. BzOH to sequentially alkylate and acylate a variety of amino acid derivatives in one pot. Solid-phase synthesis of beta-hydroxy-gamma-lactam 8, an analogue of the IL-1 modulator 101.10, was achieved using this method for studying Ser/Thr geometry.