| N-Trimethylsilyl amines for controlled ring-opening polymerization of amino acid N-carboxyanhydrides and facile end group functionalization of polypeptides. | |
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MedLine Citation:
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PMID: 18763770 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Hua Lu; Jianjun Cheng |
Publication Detail:
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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:
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Title: Journal of the American Chemical Society Volume: 130 ISSN: 1520-5126 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2008 Sep |
Date Detail:
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Created Date: 2008-09-19 Completed Date: 2008-12-01 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: United States |
Other Details:
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Languages: eng Pagination: 12562-3 Citation Subset: IM |
Affiliation:
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Department of Materials Science and Engineering, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Allylamine
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chemistry Amines / chemistry* Amino Acids / chemistry* Anhydrides / chemistry* Carbamates / chemistry Cyclization Glutamates / chemistry Peptides / chemical synthesis, chemistry* Polyglutamic Acid / analogs & derivatives, chemical synthesis Polylysine / chemical synthesis Trimethylsilyl Compounds / chemistry* |
| Chemical | |
Reg. No./Substance:
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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 |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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