Ring-opening polymerization of γ-(4-vinylbenzyl)-l-glutamate N-carboxyanhydride for the synthesis of functional polypeptides

Hua Lu, Yugang Bai, Jing Wang, Nathan P. Gabrielson, Fei Wang, Yao Lin, Jianjun Cheng

Research output: Contribution to journalArticle

Abstract

The preparation of polypeptides with poly(L-glutamate) backbone and a variety of different side chains via controlled polymerization of VB-Glu-NCA followed by a variety of highly efficient post functionalization reactions is presented. VB-Glu-NCA was readily prepared and purified in multigram scale in crystalline form. The purified VB-Glu-NCA is very stable in moisture-free conditions and can be stored in the freezer of a glovebox at 30°C for more than 6 months without noticeable change of properties. The amount of NB had very limited effect on polymerization rates and theMWs of the resulting PVBLGs, suggesting that NB functions as a radical inhibitor and does not participate in chain propagation. Notably, the aldehyde functionalized PVBLG-b was very reactive and could be used for further grafting of various functional moieties with amines, hydrazides, and oxyamines through reductive amination.

Original languageEnglish (US)
Pages (from-to)6237-6240
Number of pages4
JournalMacromolecules
Volume44
Issue number16
DOIs
StatePublished - Aug 23 2011

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Polypeptides
Ring opening polymerization
Glutamic Acid
Polymerization
Amination
Peptides
Aldehydes
Amines
Moisture
Crystalline materials

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Ring-opening polymerization of γ-(4-vinylbenzyl)-l-glutamate N-carboxyanhydride for the synthesis of functional polypeptides. / Lu, Hua; Bai, Yugang; Wang, Jing; Gabrielson, Nathan P.; Wang, Fei; Lin, Yao; Cheng, Jianjun.

In: Macromolecules, Vol. 44, No. 16, 23.08.2011, p. 6237-6240.

Research output: Contribution to journalArticle

Lu, Hua ; Bai, Yugang ; Wang, Jing ; Gabrielson, Nathan P. ; Wang, Fei ; Lin, Yao ; Cheng, Jianjun. / Ring-opening polymerization of γ-(4-vinylbenzyl)-l-glutamate N-carboxyanhydride for the synthesis of functional polypeptides. In: Macromolecules. 2011 ; Vol. 44, No. 16. pp. 6237-6240.
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AB - The preparation of polypeptides with poly(L-glutamate) backbone and a variety of different side chains via controlled polymerization of VB-Glu-NCA followed by a variety of highly efficient post functionalization reactions is presented. VB-Glu-NCA was readily prepared and purified in multigram scale in crystalline form. The purified VB-Glu-NCA is very stable in moisture-free conditions and can be stored in the freezer of a glovebox at 30°C for more than 6 months without noticeable change of properties. The amount of NB had very limited effect on polymerization rates and theMWs of the resulting PVBLGs, suggesting that NB functions as a radical inhibitor and does not participate in chain propagation. Notably, the aldehyde functionalized PVBLG-b was very reactive and could be used for further grafting of various functional moieties with amines, hydrazides, and oxyamines through reductive amination.

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