(2S,4S)-4-羟基-1,2-吡咯烷二甲酸 1-芴甲基酯 2-苄基酯 | 439290-35-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 脯氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: (2S,4S)-4-羟基-1,2-吡咯烷二甲酸 1-芴甲基酯 2-苄基酯
• 中文别名: FMOC-L-羟脯氨酸苄酯；(2S,4S)-4-羟基-1,2-吡咯烷二甲酸1-芴甲基酯2-苄基酯
• 英文名称: (2S,4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-(9H-fluoren-9-ylmethyl) ester
• 英文别名: (2S,4S)-1-((9H-Fluoren-9-yl)methyl) 2-benzyl 4-hydroxypyrrolidine-1,2-dicarboxylate；2-O-benzyl 1-O-(9H-fluoren-9-ylmethyl) (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate
• CAS: 439290-35-4
• 化学式: C₂₇H₂₅NO₅
• 分子量: 443.499
• InChiKey: CVHUWFLTKKZKSQ-DFBJGRDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4S)-4-羟基-1,2-吡咯烷二甲酸 1-芴甲基酯 2-苄基酯 在 palladium on activated charcoal N-甲基咪唑 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester
  参考文献：
  名称：

  Catalysis with Phosphine-Containing Amino Acids in Various “Turn” Motifs

  摘要：

  We have been actively involved in the development of parallel approaches for the discovery of phosphine ligands. Our approach has been based on the incorporation of phosphine-containing amino acids into peptide sequences that are designed to have stable secondary structures. We have examined helical and turn secondary structures and have reported that alkylation of cyclopentenyl acetate with dimethylmalonate can be catalyzed in high enantiomeric excess (ee) with a beta-turn-based ligand. The importance of the peptide secondary structure was demonstrated through the synthesis of a series of peptide ligands where the nature of the turn-forming residues was probed. Additionally, other turn-forming units and a variety of different phosphine-containing amino acids have been examined for their ability to control the selectivity of the allylation reaction. This paper reports the results obtained through the examination of different turn motifs as well as different phosphine substitutions on the "best" turn sequence, Pps-Pro-D-Xxx-Pps.

  DOI：

  10.1021/jo049103g
• 作为产物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 4-cis-L-hydroxyproline benzyl ester tosylate 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 以88.2%的产率得到(2S,4S)-4-羟基-1,2-吡咯烷二甲酸 1-芴甲基酯 2-苄基酯
  参考文献：
  名称：

  Catalysis with Phosphine-Containing Amino Acids in Various “Turn” Motifs

  摘要：

  We have been actively involved in the development of parallel approaches for the discovery of phosphine ligands. Our approach has been based on the incorporation of phosphine-containing amino acids into peptide sequences that are designed to have stable secondary structures. We have examined helical and turn secondary structures and have reported that alkylation of cyclopentenyl acetate with dimethylmalonate can be catalyzed in high enantiomeric excess (ee) with a beta-turn-based ligand. The importance of the peptide secondary structure was demonstrated through the synthesis of a series of peptide ligands where the nature of the turn-forming residues was probed. Additionally, other turn-forming units and a variety of different phosphine-containing amino acids have been examined for their ability to control the selectivity of the allylation reaction. This paper reports the results obtained through the examination of different turn motifs as well as different phosphine substitutions on the "best" turn sequence, Pps-Pro-D-Xxx-Pps.

  DOI：

  10.1021/jo049103g

文献信息

• The Aberrance of the 4<i>S</i> Diastereomer of 4-Hydroxyproline
  作者：Matthew D. Shoulders、Frank W. Kotch、Amit Choudhary、Ilia A. Guzei、Ronald T. Raines

  DOI：10.1021/ja103082y

  日期：2010.8.11

  typically accompany a C(gamma)-endo ring pucker. This same transannular hydrogen bond enhances an n-->pi* interaction that stabilizes the trans conformation of the peptide bond preceding hyp, endowing hyp with the unusual combination of a C(gamma)-endo ring pucker and high trans/cis ratio. O-Methylation of hyp to form (2S,4S)-4-methoxyproline (mop) eliminates the transannular hydrogen bond and restores a prototypical

  脯氨酰 4-羟化酶在原胶原、弹性蛋白和其他蛋白质中某些 (2S)-脯氨酸 (Pro) 残基的 γ-碳原子上以 4R 构型安装羟基，形成 (2S,4R)-4-羟脯氨酸 (Hyp) ）。这种普遍存在的翻译后修饰产生的粗俗效应强化了 C(gamma)-exo 环褶皱并稳定了胶原蛋白三螺旋。尽管带负电的 4S 取代基能够增强 Pro 更常见的 C(gamma)-内环褶皱，但尚未在蛋白质中观察到 Hyp 非对映异构体 (2S,4S)-4-羟脯氨酸 (hyp)。在这里，我们利用密度泛函理论、光谱学、晶体学和量热法，利用胶原蛋白模型系统探索 hyp 掺入对蛋白质稳定性的影响。我们发现 Pro 的 4S-羟基化形成 hyp 确实强制了 C(gamma)-内环褶皱，但羟基部分和 hyp 的羰基之间的跨环氢键扭曲了通常伴随 C 的主链扭转角(gamma)-endo 环褶皱。这种相同的跨环氢键增强了 n-->pi*
• Catalysis with Phosphine-Containing Amino Acids in Various “Turn” Motifs
  作者：Anton Agarkov、Scott J. Greenfield、Takahiro Ohishi、Scott E. Collibee、Scott R. Gilbertson

  DOI：10.1021/jo049103g

  日期：2004.11.1

  We have been actively involved in the development of parallel approaches for the discovery of phosphine ligands. Our approach has been based on the incorporation of phosphine-containing amino acids into peptide sequences that are designed to have stable secondary structures. We have examined helical and turn secondary structures and have reported that alkylation of cyclopentenyl acetate with dimethylmalonate can be catalyzed in high enantiomeric excess (ee) with a beta-turn-based ligand. The importance of the peptide secondary structure was demonstrated through the synthesis of a series of peptide ligands where the nature of the turn-forming residues was probed. Additionally, other turn-forming units and a variety of different phosphine-containing amino acids have been examined for their ability to control the selectivity of the allylation reaction. This paper reports the results obtained through the examination of different turn motifs as well as different phosphine substitutions on the "best" turn sequence, Pps-Pro-D-Xxx-Pps.