N-(tert-butoxycarbonyl)-(2S,4R)-4-fluoroproline N-hydroxy succinimide ester | 587887-99-8

• 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-(tert-butoxycarbonyl)-(2S,4R)-4-fluoroproline N-hydroxy succinimide ester
• 英文别名: 1-O-tert-butyl 2-O-(2,5-dioxopyrrolidin-1-yl) (2S,4R)-4-fluoropyrrolidine-1,2-dicarboxylate
• CAS: 587887-99-8
• 化学式: C₁₄H₁₉FN₂O₆
• 分子量: 330.313
• InChiKey: RARVJPVGOMLOIL-BDAKNGLRSA-N

物化性质

• 沸点：
  428.8±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-(2S,4R)-4-fluoroproline N-hydroxy succinimide ester 在 palladium on activated charcoal 氢气 、 苄基三甲基氢氧化铵 、 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 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 N-[N-[N-(tert-butoxycarbonyl)-(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-(tert-butoxycarbonyl)-(2S,4S)-4-p-nitrobenzyloxyproline benzyl ester 在 palladium on activated charcoal 氢气 、 potassium hydrogencarbonate 、 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 53.75h， 生成 N-(tert-butoxycarbonyl)-(2S,4R)-4-fluoroproline N-hydroxy succinimide ester
  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