Document Detail

N-Trimethylsilyl amines for controlled ring-opening polymerization of amino acid N-carboxyanhydrides and facile end group functionalization of polypeptides.
MedLine Citation:
PMID:  18763770     Owner:  NLM     Status:  MEDLINE    
We report a new strategy that uses N-trimethylsilyl (N-TMS) amine to mediate controlled ring-opening polymerization of amino acid N-carboxyanhydrides (NCAs). This polymerization proceeds via a unique, trimethylsilyl carbamate (TMS-CBM) propagating group that results from the cleavage of the Si-N bond of N-TMS amine followed by NCA ring opening. Propagation of the polypeptide chains proceeds through the transfer of the TMS group from the terminal TMS-CBM to the incoming monomer followed by the formation of a new TMS-CBM propagating group. Formation of the TMS-CBM was confirmed by MS and NMR. Polypeptides formed by the N-TMS amine-mediated polymerization have the expected molecular weights, narrow molecular weight distributions, and controlled functional groups at the C-termini of the polypeptides.
Hua Lu; Jianjun Cheng
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.     Date:  2008-09-03
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  130     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2008 Sep 
Date Detail:
Created Date:  2008-09-19     Completed Date:  2008-12-01     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  12562-3     Citation Subset:  IM    
Department of Materials Science and Engineering, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
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MeSH Terms
Allylamine / chemistry
Amines / chemistry*
Amino Acids / chemistry*
Anhydrides / chemistry*
Carbamates / chemistry
Glutamates / chemistry
Peptides / chemical synthesis,  chemistry*
Polyglutamic Acid / analogs & derivatives,  chemical synthesis
Polylysine / chemical synthesis
Trimethylsilyl Compounds / chemistry*
Reg. No./Substance:
0/Amines; 0/Amino Acids; 0/Anhydrides; 0/Carbamates; 0/Glutamates; 0/Peptides; 0/Trimethylsilyl Compounds; 107-11-9/Allylamine; 25014-27-1/poly-gamma-benzyl-L-glutamate; 25104-18-1/Polylysine; 25513-46-6/Polyglutamic Acid

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