Splicing of Unnatural Amino Acids Into Proteins: A Peptide Model Study

Author(s): Shoufa Han, Ronald E. Viola.

Journal Name: Protein & Peptide Letters

Volume 11 , Issue 2 , 2004

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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.

Keywords: phosphinothiol,, peptide coupling,, unnatural amino acid incorporation,, Staudinger ligation,

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Article Details

Year: 2004
Page: [107 - 114]
Pages: 8
DOI: 10.2174/0929866043478301
Price: $58

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