(S)-3-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyryl]-2,2-dimethyl-oxazolidine-4-carboxylic acid benzyl ester | 186023-48-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyryl]-2,2-dimethyl-oxazolidine-4-carboxylic acid benzyl ester
• 英文别名: benzyl (4S)-3-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutanoyl]-2,2-dimethyl-1,3-oxazolidine-4-carboxylate
• CAS: 186023-48-3
• 化学式: C₃₃H₃₆N₂O₆
• 分子量: 556.659
• InChiKey: LMFOTTBXOXGCCB-VMPREFPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  94.17
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-3-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyryl]-2,2-dimethyl-oxazolidine-4-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (4S)-3-[(2S)-2-[[芴甲氧羰基]氨基]-3-甲基-1-氧代丁基]-2,2-二甲基-4-恶唑烷羧酸
  参考文献：
  名称：

  Pseudo-Prolines as a Molecular Hinge:  Reversible Induction of cis Amide Bonds into Peptide Backbones

  摘要：

  Serine, threonine-derived (4S)-oxazolidine-4-carboxylic acid, and cysteine-derived (4R)-thiazolidinecarboxylic acid, denoted pseudo-proline (Xaa[Psi(R1,R2)pro]), serve as structure disrupting, solubilizing building blocks in peptide synthesis. Variation of the 2-C substituents within the heterocyclic system results in different physicochemical and conformational properties. NMR studies of a series of pseudo-proline (Psi Pro)-containing peptides reveal a pronounced effect of the 2-C substituents upon the cis to trans ratio of the adjacent amide bond in solution. 2-C unsubstituted systems show a preference similar to that of the proline residue for the trans form, whereas 2,2-dimethylated derivatives adopt the cis amide conformation in high content. For 2-monosubstituted Psi Pro, the cis-trans distribution depends on the 2-C chirality. For the 2-(S)-diastereoisomer, both forms are similarly populated in solution, whereas the 2-(R)-epimer adopts preferentially the trans form. The results are supported by conformational energy calculations and suggest that, by tailoring the degree of substitution, pseudo-prolines may serve as a temporary proline mimetic or as a hinge in peptide backbones.

  DOI：

  10.1021/ja962780a
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 L-丝氨酸,N-[(9H-芴-9-基甲氧基)羰基]-L-缬氨酰-,苯基甲基酯 在 4-甲基苯磺酸吡啶 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 15.0h， 以49%的产率得到(S)-3-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyryl]-2,2-dimethyl-oxazolidine-4-carboxylic acid benzyl ester
  参考文献：
  名称：

  Pseudo-Prolines as a Molecular Hinge:  Reversible Induction of cis Amide Bonds into Peptide Backbones

  摘要：

  Serine, threonine-derived (4S)-oxazolidine-4-carboxylic acid, and cysteine-derived (4R)-thiazolidinecarboxylic acid, denoted pseudo-proline (Xaa[Psi(R1,R2)pro]), serve as structure disrupting, solubilizing building blocks in peptide synthesis. Variation of the 2-C substituents within the heterocyclic system results in different physicochemical and conformational properties. NMR studies of a series of pseudo-proline (Psi Pro)-containing peptides reveal a pronounced effect of the 2-C substituents upon the cis to trans ratio of the adjacent amide bond in solution. 2-C unsubstituted systems show a preference similar to that of the proline residue for the trans form, whereas 2,2-dimethylated derivatives adopt the cis amide conformation in high content. For 2-monosubstituted Psi Pro, the cis-trans distribution depends on the 2-C chirality. For the 2-(S)-diastereoisomer, both forms are similarly populated in solution, whereas the 2-(R)-epimer adopts preferentially the trans form. The results are supported by conformational energy calculations and suggest that, by tailoring the degree of substitution, pseudo-prolines may serve as a temporary proline mimetic or as a hinge in peptide backbones.

  DOI：

  10.1021/ja962780a