Document Detail

Splicing of unnatural amino acids into proteins: a peptide model study.
MedLine Citation:
PMID:  15078198     Owner:  NLM     Status:  MEDLINE    
S-Ethyl 2-azidohexanethioate (N3-Hex-SEt), an unnatural amino acid analog of leucine, is coupled with L-cysteine ethyl ester (NH2-Cys-OEt) to obtain N3-Hex-Cys-OEt by native chemical ligation. Coupling of this dipeptide with N-t-butoxycarbonyl-2-diphenylphosphinoethanethioglycinate produces the tripeptide, t-Boc-Gly-Hex-Cys-OEt, in high yield. These reactions suggest an approach for the incorporation of unnatural amino acids into proteins by successive native chemical ligation and Staudinger ligation.
Shoufa Han; Ronald E Viola
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  Protein and peptide letters     Volume:  11     ISSN:  0929-8665     ISO Abbreviation:  Protein Pept. Lett.     Publication Date:  2004 Apr 
Date Detail:
Created Date:  2004-04-13     Completed Date:  2004-10-28     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9441434     Medline TA:  Protein Pept Lett     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  107-14     Citation Subset:  IM    
University of Toledo, Department of Chemistry, Toledo, Ohio 43606, USA.
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MeSH Terms
Cysteine / analogs & derivatives*,  chemistry*
Leucine / analogs & derivatives*,  chemistry*
Models, Chemical*
Molecular Structure
Oligopeptides / chemical synthesis*,  chemistry*
Proteins / chemistry*
Reg. No./Substance:
0/Oligopeptides; 0/Proteins; 3411-58-3/ethyl cysteine; 52-90-4/Cysteine; 61-90-5/Leucine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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