Zhao Yi-nan, Melanie Key
2013
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Journal
Chemistry World
Abstract
The research of polypeptides on the physiological process of human beings could provide prevention and treatment methods to some diseases.However,there are some disadvantages concerning the syntheses of these polypeptides,such as expensive materials,low yield,and difficulty to purify,so it is necessary to simplify and improve the synthetic method of polypeptides.Lysine and glycine are chosen as raw materials in this study.In water/acetone solvent system,di-tert-butyl dicarbonate(Boc2O)and 9-fluorenylmethoxycarbonyl(Fmoc-OSu)were used to protecte-amino andα-amino of lysine,respectively,for preparing Fmoc-L-Lys(Boc)-OH.Then 2-(7-azobenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate(HATU)was employed as condensation reagent to activate Fmoc-L-Lys(Boc)-OH to form active ester.In acetonitrile/water solvent system,the activated Fmoc-L-Lys(Boc)-OH was reacted with glycine under refluxing at 50~60℃for 5hto give the dipetide Fmoc-L-Lys(Boc)-Gly-OH which’s structure was confirmed by IR and MS spectra.The study could provide the experimental basis and theoretical reference for amino protection reaction and polypeptide synthesis.