Fast and Convenient Synthesis of Amine-Terminated Polylactide as a Macroinitiator for ω-Benzyloxycarbonyl-L-Lysine-N-Carboxyanhydrides

Fast and Convenient Synthesis of Amine-Terminated Polylactide as a Macroinitiator for ω-Benzyloxycarbonyl-L-Lysine-N-Carboxyanhydrides

Amine-terminated poly (L-lactide) (NH2-PLLA) with various chain lengths were successfully synthesized by sequential tert-butyl-N-(3-hydroxypropyl) carbamate initiated bulk ring-opening polymerization (ROP) of L-lactide (L-LA) in the presence of Stannous(II) 2-ethylhexanoate (Sn(Oct)2) and deprotecti...

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Main Authors: Mingjie Ju, Feirong Gong, Shujun Cheng, Yun Gao
Format: Article
Language:English
Published: Hindawi Limited 2011-01-01
Series:International Journal of Polymer Science
Online Access:http://dx.doi.org/10.1155/2011/381076
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spelling doaj-343fef61b4c4493781c68c75fb5ee2612020-11-24T21:07:16ZengHindawi LimitedInternational Journal of Polymer Science1687-94221687-94302011-01-01201110.1155/2011/381076381076Fast and Convenient Synthesis of Amine-Terminated Polylactide as a Macroinitiator for ω-Benzyloxycarbonyl-L-Lysine-N-CarboxyanhydridesMingjie Ju0Feirong Gong1Shujun Cheng2Yun Gao3Key Laboratory for Ultrafine Materials of Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, ChinaKey Laboratory for Ultrafine Materials of Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, ChinaKey Laboratory for Ultrafine Materials of Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, ChinaKey Laboratory for Ultrafine Materials of Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, ChinaAmine-terminated poly (L-lactide) (NH2-PLLA) with various chain lengths were successfully synthesized by sequential tert-butyl-N-(3-hydroxypropyl) carbamate initiated bulk ring-opening polymerization (ROP) of L-lactide (L-LA) in the presence of Stannous(II) 2-ethylhexanoate (Sn(Oct)2) and deprotection of the N-tert-butoxycarbonyl (Boc) group at the end of the polymer chain. The polymers obtained were characterized by FT-IR, 1H NMR, and GPC method. NH2-PLLA thus prepared was used to initiate the polymerization of ω-benzyloxycarbonyl-L-lysine-N-carboxyanhydride (Lys (Z)-NCA), and the result confirmed the high nucleophilicity of the terminal amine group. This method was not only suitable for the preparation of low molecular weight NH2-PLLA, but also quite efficient in the synthesis of high molecular weight samples.http://dx.doi.org/10.1155/2011/381076
collection DOAJ
language English
format Article
sources DOAJ
author Mingjie Ju
Feirong Gong
Shujun Cheng
Yun Gao
spellingShingle Mingjie Ju
Feirong Gong
Shujun Cheng
Yun Gao
Fast and Convenient Synthesis of Amine-Terminated Polylactide as a Macroinitiator for ω-Benzyloxycarbonyl-L-Lysine-N-Carboxyanhydrides
International Journal of Polymer Science
author_facet Mingjie Ju
Feirong Gong
Shujun Cheng
Yun Gao
author_sort Mingjie Ju
title Fast and Convenient Synthesis of Amine-Terminated Polylactide as a Macroinitiator for ω-Benzyloxycarbonyl-L-Lysine-N-Carboxyanhydrides
title_short Fast and Convenient Synthesis of Amine-Terminated Polylactide as a Macroinitiator for ω-Benzyloxycarbonyl-L-Lysine-N-Carboxyanhydrides
title_full Fast and Convenient Synthesis of Amine-Terminated Polylactide as a Macroinitiator for ω-Benzyloxycarbonyl-L-Lysine-N-Carboxyanhydrides
title_fullStr Fast and Convenient Synthesis of Amine-Terminated Polylactide as a Macroinitiator for ω-Benzyloxycarbonyl-L-Lysine-N-Carboxyanhydrides
title_full_unstemmed Fast and Convenient Synthesis of Amine-Terminated Polylactide as a Macroinitiator for ω-Benzyloxycarbonyl-L-Lysine-N-Carboxyanhydrides
title_sort fast and convenient synthesis of amine-terminated polylactide as a macroinitiator for ω-benzyloxycarbonyl-l-lysine-n-carboxyanhydrides
publisher Hindawi Limited
series International Journal of Polymer Science
issn 1687-9422
1687-9430
publishDate 2011-01-01
description Amine-terminated poly (L-lactide) (NH2-PLLA) with various chain lengths were successfully synthesized by sequential tert-butyl-N-(3-hydroxypropyl) carbamate initiated bulk ring-opening polymerization (ROP) of L-lactide (L-LA) in the presence of Stannous(II) 2-ethylhexanoate (Sn(Oct)2) and deprotection of the N-tert-butoxycarbonyl (Boc) group at the end of the polymer chain. The polymers obtained were characterized by FT-IR, 1H NMR, and GPC method. NH2-PLLA thus prepared was used to initiate the polymerization of ω-benzyloxycarbonyl-L-lysine-N-carboxyanhydride (Lys (Z)-NCA), and the result confirmed the high nucleophilicity of the terminal amine group. This method was not only suitable for the preparation of low molecular weight NH2-PLLA, but also quite efficient in the synthesis of high molecular weight samples.
url http://dx.doi.org/10.1155/2011/381076
work_keys_str_mv AT mingjieju fastandconvenientsynthesisofamineterminatedpolylactideasamacroinitiatorforōbenzyloxycarbonylllysinencarboxyanhydrides
AT feironggong fastandconvenientsynthesisofamineterminatedpolylactideasamacroinitiatorforōbenzyloxycarbonylllysinencarboxyanhydrides
AT shujuncheng fastandconvenientsynthesisofamineterminatedpolylactideasamacroinitiatorforōbenzyloxycarbonylllysinencarboxyanhydrides
AT yungao fastandconvenientsynthesisofamineterminatedpolylactideasamacroinitiatorforōbenzyloxycarbonylllysinencarboxyanhydrides
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