Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (12): 2119-2125. Previous Articles     Next Articles

Original Articles

微波作用下大位阻氨基酸与H-Pro-CTC树脂的高效缩合

张 俊a ; 杨 明a ;王安明a ; 王 华a ; 周 成a ; 杜志强a; 祝社民b; 沈树宝*,a
  

  1. (a南京工业大学制药与生命科学学院 材料化学工程国家重点实验室 南京 210009)
    (b南京工业大学材料科学与工程学院 材料化学工程国家重点实验室 南京 210009)
  • 收稿日期:2007-12-21 修回日期:2008-06-19 发布日期:2008-12-28
  • 通讯作者: 沈树宝

Highly Efficient Coupling of Sterically Hindered Amino Acids to H-Pro-CTC Resin under Microwave Irradiation

ZHANG, Juna; YANG, Ming a; WANG, An-Minga; WANG, Huaa ; ZHOU, Chenga;
DU, Zhi-Qianga; ZHU, She-Minb ; SHEN, Shu-Bao*,a
  

  1. (a State Key Laboratory of Materials-oriented Chemical Engineering, College of Life Science and Pharmaceutical
    Engineering, Nanjing University of Technology, Nanjing 210009)
    (b State Key Laboratory of Materials-oriented Chemical Engineering, College of Material Science and Engineering,
    Nanjing University of Technology, Nanjing 210009)
  • Received:2007-12-21 Revised:2008-06-19 Published:2008-12-28
  • Contact: SHEN, Shu-Bao

Under microwave irradiation, five sterically hindered amino acids were coupled to H-Pro-CTC resin (CTC resin, 2-chlorotrityl chloride resin) in a novel solid-phase peptide synthesis (SPPS) reactor, severally. The triple coupling method was carried out using DMF/NMP/THF (V∶V∶V=1∶1∶1), NMP/DMSO/THF (V∶V∶V=4∶1∶1), DMF/DMSO/THF (V∶V∶V=4∶1∶1) as solvent. The optimal conditions in-cluding coupling reagent, concentration of amino acids, microwave irritation time, reaction temperature and maintaining time were HBTU, 7 mmol/L, 3 min, 35 ℃ and 3 min for every coupling, respectively. Compared with the conventional method which was not microwave-assisted, the excess of sterically hindered amino acids decreased from 5-fold to 2-fold and the coupling reaction rate increased by over 16 times. The coupling yields of the five sterically hindered amino acids to H-Pro-CTC resin were all improved to over 80%.

Key words: solid-phase peptide synthesis (SPPS), microwave, reactor, sterically hindered amino acid