N-[N-(tert-butoxycarbonyl)-(2S,4R)-4-fluoroprolyl]-2S-proline | 587888-00-4

• 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: N-[N-(tert-butoxycarbonyl)-(2S,4R)-4-fluoroprolyl]-2S-proline
• 英文别名: (2S)-1-[(2S,4R)-4-fluoro-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylic acid
• CAS: 587888-00-4
• 化学式: C₁₅H₂₃FN₂O₅
• 分子量: 330.356
• InChiKey: HUNGHGKPCBNHLY-VWYCJHECSA-N

物化性质

• 沸点：
  510.2±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  87.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[N-(tert-butoxycarbonyl)-(2S,4R)-4-fluoroprolyl]-2S-proline 在 palladium on activated charcoal 盐酸 、 氢气 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 N-[N-[N-(fluorenylmethoxycarbonyl)-(2S,4R)-4-fluoroprolyl]-2S-prolyl]-glycine
  参考文献：
  名称：

  Stereoelectronic Effects on Collagen Stability:  The Dichotomy of 4-Fluoroproline Diastereomers

  摘要：

  Collagen is the most abundant protein in animals. Natural collagen consists of a triple helix of (Xaa-Yaa-Gly)n chains, in which the Xaa and Yaa residues are often l-proline. Here, a (2S,4S)-4-fluoroproline (flp) residue is shown to be greatly stabilizing in the Xaa position (but destabilizing in the Yaa position). In contrast, a (2S,4R)-4-fluoroproline (Flp) residue is shown to be greatly destabilizing in the Xaa position (but stabilizing in the Yaa position). The dichotomous effect of the diastereomers appears to arise from a gauche effect, which alters pyrrolidine ring pucker and hence properly (or improperly) preorganizes main-chain dihedral angles. Thus, the rational use of stereoelectronic effects can enhance the conformational stability of a protein.

  DOI：

  10.1021/ja035881z
• 作为产物：
  描述：

  N-Boc-反式-4-氟-L-脯氨酸 在 苄基三甲基氢氧化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 14.0h， 生成 N-[N-(tert-butoxycarbonyl)-(2S,4R)-4-fluoroprolyl]-2S-proline
  参考文献：
  名称：

  Stereoelectronic Effects on Collagen Stability:  The Dichotomy of 4-Fluoroproline Diastereomers

  摘要：

  Collagen is the most abundant protein in animals. Natural collagen consists of a triple helix of (Xaa-Yaa-Gly)n chains, in which the Xaa and Yaa residues are often l-proline. Here, a (2S,4S)-4-fluoroproline (flp) residue is shown to be greatly stabilizing in the Xaa position (but destabilizing in the Yaa position). In contrast, a (2S,4R)-4-fluoroproline (Flp) residue is shown to be greatly destabilizing in the Xaa position (but stabilizing in the Yaa position). The dichotomous effect of the diastereomers appears to arise from a gauche effect, which alters pyrrolidine ring pucker and hence properly (or improperly) preorganizes main-chain dihedral angles. Thus, the rational use of stereoelectronic effects can enhance the conformational stability of a protein.

  DOI：

  10.1021/ja035881z

文献信息

• Collagen mimics
  申请人：Raines T. Ronald

  公开号：US20050004032A1

  公开（公告）日：2005-01-06

  A novel collagen mimic comprising a tripeptide unit having the formula (flpYaaGly) n , where flp is 4(S)-fluoro-L-proline, is disclosed. The collagen mimic has increased stability relative to the collagen-related triple helices (ProYaaGly) n , (hypYaaGly) n , and (HypYaaGly) n .

  披露了一种新颖的胶原蛋白模拟物，该模拟物包含一个三肽单元，其公式为(fl pYaaGly) n，其中fl p代表4 (S)-氟-L-脯氨酸。与胶原蛋白相关三螺旋(ProYaaGly) n、(hypYaaGly) n和(HypYaaGly) n相比，该胶原蛋白模拟物具有更高的稳定性。
• US7122521B2
  申请人：——

  公开号：US7122521B2

  公开（公告）日：2006-10-17
• Stereoelectronic Effects on Collagen Stability:  The Dichotomy of 4-Fluoroproline Diastereomers
  作者：Jonathan A. Hodges、Ronald T. Raines

  DOI：10.1021/ja035881z

  日期：2003.8.1

  Collagen is the most abundant protein in animals. Natural collagen consists of a triple helix of (Xaa-Yaa-Gly)n chains, in which the Xaa and Yaa residues are often l-proline. Here, a (2S,4S)-4-fluoroproline (flp) residue is shown to be greatly stabilizing in the Xaa position (but destabilizing in the Yaa position). In contrast, a (2S,4R)-4-fluoroproline (Flp) residue is shown to be greatly destabilizing in the Xaa position (but stabilizing in the Yaa position). The dichotomous effect of the diastereomers appears to arise from a gauche effect, which alters pyrrolidine ring pucker and hence properly (or improperly) preorganizes main-chain dihedral angles. Thus, the rational use of stereoelectronic effects can enhance the conformational stability of a protein.