(4S,5R)-3-[(2S)-2-[[芴甲氧羰基]氨基]-1-氧代-3-苯基丙基]-2,2,5-三甲基-4-恶唑烷羧酸 | 1196703-48-6

• 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
• 中文名称: (4S,5R)-3-[(2S)-2-[[芴甲氧羰基]氨基]-1-氧代-3-苯基丙基]-2,2,5-三甲基-4-恶唑烷羧酸
• 英文名称: Fmoc-Phe-Thr(Ψ-Me,Me pro)-OH
• 英文别名: Fmoc-Phe-Thr(Psi(Me,Me)pro)-OH；(4S,5R)-3-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoyl]-2,2,5-trimethyl-1,3-oxazolidine-4-carboxylic acid
• CAS: 1196703-48-6
• 化学式: C₃₁H₃₂N₂O₆
• 分子量: 528.605
• InChiKey: FFOYZGOZWLCJDO-VHEIIQRDSA-N

物化性质

• 沸点：
  764.4±60.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

生物活性方面，Fmoc-Phe-Thr(psi(Me,Me)pro)-OH 是一种二肽。

反应信息

• 作为反应物：
  描述：

  (4S,5R)-3-[(2S)-2-[[芴甲氧羰基]氨基]-1-氧代-3-苯基丙基]-2,2,5-三甲基-4-恶唑烷羧酸 在 trityl chloride polystyrene resin 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以145 mg的产率得到NH2-Phe-Thr(ψ-Me,Mepro)-Phe-Thr(ψ-Me,Mepro)-OH
  参考文献：
  名称：

  Synthesis of All-l Cyclic Tetrapeptides Using Pseudoprolines as Removable Turn Inducers

  摘要：

  Cyclic tetrapeptides h we generated great interest because of their broad-ranging biological properties. In order to synthesize these highly strained 12-membered cyclic compounds, a cyclization strategy using pseudoprolines as removable turn inducers has been developed. The pseudoproline derivatives induce a cisoid amide bond in the linear peptide backbone which facilitates cyclization. After cyclization, the turn inducers can be readily removed to afford cyclic tetrapeptides containing serine or threonine residues.

  DOI：

  10.1021/ol101018w

文献信息

• INSULINOTROPIC PEPTIDE SYNTHESIS USING SOLID AND SOLUTION PHASE COMBINATION TECHNIQUES
  申请人：Corden Pharma Colorado, Inc.

  公开号：EP2205624B1

  公开（公告）日：2016-09-07
• Insulinotropic peptide synthesis using solid and solution phase combination techniques
  申请人：King Barry Thomas

  公开号：US20090149628A1

  公开（公告）日：2009-06-11

  The present invention relates to the preparation of insulinotropic peptides that are synthesized using a solid and solution phase (“hybrid”) approach. Generally, the approach includes synthesizing three different peptide intermediate fragments using solid phase chemistry. Solution phase chemistry is then used to add additional amino acid material to one of the fragments. The fragments are then coupled together in the solution phase. The use of a pseudoproline in one of the fragments eases solid phase synthesis of that fragment and also eases subsequent solution phase coupling of this fragment to other fragments. The present invention is very useful for forming insulinotropic peptides such as Exenatide(1-39) and its natural and non-natural counterparts.
• US8378066B2
  申请人：——

  公开号：US8378066B2

  公开（公告）日：2013-02-19
• Synthesis of All-<scp>l</scp> Cyclic Tetrapeptides Using Pseudoprolines as Removable Turn Inducers
  作者：Kelly A. Fairweather、Nima Sayyadi、Ian J. Luck、Jack K. Clegg、Katrina A. Jolliffe

  DOI：10.1021/ol101018w

  日期：2010.7.16

  Cyclic tetrapeptides h we generated great interest because of their broad-ranging biological properties. In order to synthesize these highly strained 12-membered cyclic compounds, a cyclization strategy using pseudoprolines as removable turn inducers has been developed. The pseudoproline derivatives induce a cisoid amide bond in the linear peptide backbone which facilitates cyclization. After cyclization, the turn inducers can be readily removed to afford cyclic tetrapeptides containing serine or threonine residues.