Abstract
[reaction: see text] A novel strategy to generate thioester peptides compatible with Fmoc chemistry is presented. Peptide-C(alpha)oxy-(2-mercapto-1-carboxyamide)ethyl ester undergoes an O to S acyl shift during ligation and the newly formed thioester intermediate reacts with an N-terminal cysteine fragment generating a product with native amide bond at the ligation site.
MeSH terms
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Amides / chemistry
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Chromatography, High Pressure Liquid
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Cysteine / chemistry
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Hydrogen-Ion Concentration
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Ligands
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Molecular Structure
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Oxygen / chemistry*
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Peptides / chemical synthesis*
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Peptides / chemistry
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Sensitivity and Specificity
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Sulfur / chemistry*
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Sulfuric Acid Esters / chemical synthesis*
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Sulfuric Acid Esters / chemistry
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Time Factors
Substances
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Amides
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Ligands
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Peptides
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Sulfuric Acid Esters
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Sulfur
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Cysteine
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Oxygen