Synthesis of depsipeptides from L-amino acids and lactones  

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作  者:Hongfei CAO Yakai FENG Heyun WANG Li ZHANG Musammir KHAN Jintang GUO 

机构地区:[1]School of Chemical Engineering and Technology,Tianjin University,Tianjin 300072,China [2]Tianjin University-Helmholtz-Zentrum Geesthacht,Joint Laboratory for Biomaterials and Regenerative Medicine,Tianjin 300072,China,Teltow 14513,Germany

出  处:《Frontiers of Chemical Science and Engineering》2011年第4期409-415,共7页化学科学与工程前沿(英文版)

基  金:financially supported by Program for the New Century Excellent Talents in University“NCET”,Ministry of Education of China,and by the International Cooperation from Ministry of Science and Technology of China(Grant No.2008DFA51170);sponsored by the Scientific Research Foundation for the Returned Overseas Chinese Scholars,Ministry of Education of China.

摘  要:By using the corresponding L-amino acid sodium as initiator,ε-caprolactone-depsipeptides CL-Ala and CL-Leu were prepared by the reactions ofε-caprolactone(CL)with L-alanine and L-leucine,respec-tively,and p-dioxanone-depsipeptide(PDO-Leu)was prepared by the reaction of p-dioxanone(PDO)with L-leucine.Two poly(ε-caprolactone)oligomers(PCL-Ala and PCL-Leu)of different molecular weights with depsipeptide unit were synthesized by controlling the feed ratio of L-amino acid sodium and CL.The presence of the depsipeptide structure in these obtained products was confirmed by 1H NMR spectra and the molecular weight of the poly(ε-caprolactone)oligomers was measured by gel permeation chromatography(GPC).These products con-tain a hydroxyl group and a carboxyl group in one molecule,which means they could act as bifunctional monomers for further polymerization to prepare high molecular weight polymers.By this way,the depsipeptide unit could be introduced into the polymers and the biodegradation rates of the novel polymers could be well controlled in vivo by the tailored molecular structures.

关 键 词:ε-caprolactone P-DIOXANONE L-ALANINE L-LEUCINE DEPSIPEPTIDE 

分 类 号:O63[理学—高分子化学]

 

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