Boc-(S)-Ser-(S-ec)-(S)-Pro-OH | 150807-10-6

• 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: Boc-(S)-Ser-(S-ec)-(S)-Pro-OH
• 英文别名: (3S,6S,8aS)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-2,3,6,7,8,8a-hexahydropyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid
• CAS: 150807-10-6
• 化学式: C₁₃H₂₀N₂O₆
• 分子量: 300.312
• InChiKey: AEQMMOBDRXTUTB-CIUDSAMLSA-N

物化性质

• 沸点：
  537.6±50.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  Boc-(S)-Ser-(S-ec)-(S)-Pro-OH 在 二苯基膦叠氮化物 作用下， 生成 (3S,6S,8aS)-3-[2-(2,4-Dinitro-phenylamino)-acetylamino]-4-oxo-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid [(4-nitro-phenylcarbamoyl)-methyl]-amide
  参考文献：
  名称：

  Synthesis of potential β-turn bicyclic dipeptide mimetics

  摘要：

  描述了四种非对映异构双环内酰胺的合成，旨在

  DOI：

  10.1039/c39930000935
• 作为产物：
  描述：

  Boc-Ser-Pro-OMe 在 sodium hydroxide 、 tetrabutylammonium tetrafluoroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.0h， 生成 Boc-(S)-Ser-(S-ec)-(S)-Pro-OH
  参考文献：
  名称：

  Electrochemical Cyclization of Dipeptides To Form Novel Bicyclic, Reverse-Turn Peptidomimetics. 2. Synthesis and Conformational Analysis of 6,5-Bicyclic Systems

  摘要：

  Novel, highly constrained, 6,5-bicyclic dipeptides (1-aza-5-oxa-2-oxoibicyclo[4.3.0]nonane ring skeletons, 2) have been synthesized by a one-step electrochemical cyclization from the dipeptides Boc-(S)-serine-(S)-proline-OMe (Boc-(S)-Ser-(S)-Pro-OMe, 3) and Boc-(R,S)-alpha-methylserine-(S)-proline-OMe (Boc-(R,S)-alpha-MeS-(S)-Pro-OMe, 12) in yields of 10-25% and 41%, respectively. The one-pot reaction uses selective anodic amide oxidation to generate an N-acyliminium cation which is trapped by an intramolecular hydroxyl group. The cyclization of Boc-(S)-Ser-(S)-Pro-OMe (3) to the 6,5-bicyclic skeleton 4 was highly diastereoselective, generating a new chiral center with an S configuration. This bicyclic compound was sufficiently stable to trifluoroacetic acid and anhydrous hydrofluoric acid for use in standard solid phase peptide synthesis methodologies. Oxidation of Boc-(R,S)-MeS-(S)-Pro-OMe (12) gave different results for each diastereoisomer. Cyclization only occurred for the S,S-diastereoisomer with very low stereoselectivity (6:4 ratio of diastereomers) at the newly-formed ring fusion. In terms of conformation, the 6,5-bicyclic system restricts two (psi(2) and phi(3)) Of the four torsion angles that characterize a reverse turn. Conformational analyses of tetrapeptides containing the 6,5-bicyclic system were performed using Monte Carlo conformational searches and molecular dynamics simulations. AU of the eight possible diastereomers arising from the three stereogenic centers (Ser C alpha, Pro C alpha, and newly formed bridgehead) were considered. These studies revealed that the 3S,7S,10S and 3R,7R,10R configurations are effective turn inducers although the torsion angles of the backbone do not exactly mimic those of classical beta-turns. Other diastereomers were found to stabilize the peptide backbone in an extended conformation.

  DOI：

  10.1021/jo950898o

文献信息

• Synthesis of potential β-turn bicyclic dipeptide mimetics
  作者：Jack E. Baldwin、Christopher Hulme、Christopher J. Schofield、Alison J. Edwards

  DOI：10.1039/c39930000935

  日期：——

  The syntheses of four diastereoisomeric bicyclic lactams, intended for analysis as β-turn-inducing mimetics, are described; the crystal structure of one derivative has been reported.

  描述了四种非对映异构双环内酰胺的合成，旨在
• Electrochemical Cyclization of Dipeptides To Form Novel Bicyclic, Reverse-Turn Peptidomimetics. 2. Synthesis and Conformational Analysis of 6,5-Bicyclic Systems
  作者：Urszula Slomczynska、David K. Chalmers、Fabrice Cornille、Mark L. Smythe、Denise D. Beusen、Kevin D. Moeller、Garland R. Marshall

  DOI：10.1021/jo950898o

  日期：1996.1.1

  Novel, highly constrained, 6,5-bicyclic dipeptides (1-aza-5-oxa-2-oxoibicyclo[4.3.0]nonane ring skeletons, 2) have been synthesized by a one-step electrochemical cyclization from the dipeptides Boc-(S)-serine-(S)-proline-OMe (Boc-(S)-Ser-(S)-Pro-OMe, 3) and Boc-(R,S)-alpha-methylserine-(S)-proline-OMe (Boc-(R,S)-alpha-MeS-(S)-Pro-OMe, 12) in yields of 10-25% and 41%, respectively. The one-pot reaction uses selective anodic amide oxidation to generate an N-acyliminium cation which is trapped by an intramolecular hydroxyl group. The cyclization of Boc-(S)-Ser-(S)-Pro-OMe (3) to the 6,5-bicyclic skeleton 4 was highly diastereoselective, generating a new chiral center with an S configuration. This bicyclic compound was sufficiently stable to trifluoroacetic acid and anhydrous hydrofluoric acid for use in standard solid phase peptide synthesis methodologies. Oxidation of Boc-(R,S)-MeS-(S)-Pro-OMe (12) gave different results for each diastereoisomer. Cyclization only occurred for the S,S-diastereoisomer with very low stereoselectivity (6:4 ratio of diastereomers) at the newly-formed ring fusion. In terms of conformation, the 6,5-bicyclic system restricts two (psi(2) and phi(3)) Of the four torsion angles that characterize a reverse turn. Conformational analyses of tetrapeptides containing the 6,5-bicyclic system were performed using Monte Carlo conformational searches and molecular dynamics simulations. AU of the eight possible diastereomers arising from the three stereogenic centers (Ser C alpha, Pro C alpha, and newly formed bridgehead) were considered. These studies revealed that the 3S,7S,10S and 3R,7R,10R configurations are effective turn inducers although the torsion angles of the backbone do not exactly mimic those of classical beta-turns. Other diastereomers were found to stabilize the peptide backbone in an extended conformation.