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

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

(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, Jun^a; YANG, Ming ^a; WANG, An-Ming^a; WANG, Hua^a ; ZHOU, Cheng^a;
DU, Zhi-Qiang^a; ZHU, She-Min^b ; SHEN, Shu-Bao^*,a

(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

Abstract

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

Cite this article

ZHANG, Jun^a; YANG, Ming ^a; WANG, An-Ming^a; WANG, Hua^a ; ZHOU, Cheng^a;
DU, Zhi-Qiang^a; ZHU, She-Min^b ; SHEN, Shu-Bao^*,a
. Highly Efficient Coupling of Sterically Hindered Amino Acids to H-Pro-CTC Resin under Microwave Irradiation[J]. Chin. J. Org. Chem., 2008, 28(12): 2119-2125.

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微波作用下大位阻氨基酸与H-Pro-CTC树脂的高效缩合

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

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