vanderdonk - Expanding the Genetic Code 1. Modifying...

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Expanding the Genetic Code 1. Modifying existing amino acids 2. Incorporating non-proteinogenic amino acids using the ribosome 3. Incorporating non-proteinogenic amino acids using the protein splicing machinery References as given in the summary. 34-66
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Modifying Existing Amino Acids Nucleophilic residues: Problem: many Lys or Cys residues in proteins and not always where you want them NH O O I NH 2 O R S S O O N O O O O R
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Need chemoselective reactions
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How to get one of the chemoselective coupling partners into a protein? Early methods: Oxidation of N-terminal Ser/Thr: H 2 N protein HO R O NaIO 4 O protein O R O only 1,2 diols or 1,2 aminoalcohols react ligate Geoghegan, K. F.; Stroh, J. G. Bioconj. Chem. 1992 , 3, 138-146.
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Link two large synthetic peptides S te phe n Ke nt, S c ie nc e  1994 266 , 776
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Newer ligation techniques: Click chemistry (azide-alkyne cycloadditions) Sharpless Staudinger ligation Bertozzi (next week) R N N N R 1 Cu N N N R R 1 triazole N N N R 1 OMe O R PPh 2 N H O R PPh 2 R 1
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Using the ribosome to incorporate non- proteinogenic amino acids tRNA a ntic o do n
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The Genetic Code S to p c o do ns : UAA, UG A, UAG
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1.
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This note was uploaded on 12/04/2011 for the course CHEM 590A taught by Professor Staff during the Summer '10 term at University of Illinois, Urbana Champaign.

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vanderdonk - Expanding the Genetic Code 1. Modifying...

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