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Chinese Journal of Organic Chemistry 2008, 28(12) 2119-2125 DOI:
ISSN: 0253-2786 CN: 31-1321/O6 |
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| Original Articles |
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Highly Efficient Coupling of Sterically Hindered Amino Acids to H-Pro-CTC Resin under Microwave Irradiation |
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ZHANG, Juna; YANG, Ming a; WANG, An-Minga; WANG, Huaa ; ZHOU, Chenga; DU, Zhi-Qianga; ZHU, She-Minb ; SHEN, Shu-Bao*,a
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(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)
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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%. |
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Keywords:
microwave
solid-phase peptide synthesis (SPPS)
reactor
sterically hindered amino acid
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Received 2007-12-21 Revised 2008-06-19 Online: |
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Corresponding Authors: SHEN, Shu-Bao |
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