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• W2605396427 abstract "General conditions for efficient on-resin N-formylation of peptides were identified by screening of a number of reagents comprising aliphatic formates (ethyl formate, 2,2,2-trifluoroethyl formate, and cyanomethyl formate), aromatic esters (phenyl formate and p-nitrophenyl formate), and N-formylimidazole and in situ activation of formic acid with the coupling reagent 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide. Initially, reaction time and influence of solvent were examined for the formylation of a short model peptide. The most efficient reagents were examined further by using different linkers and solid supports in the synthesis of an array of longer formyl peptide ligands. For p-nitrophenyl formate and N-formylimidazole, almost complete conversion was reached within 2 h, albeit longer peptides attached to Tentagel resins via different linkers required an extended reaction time. Overall, the commercially available activated ester p-nitrophenyl formate proved to be most convenient and versatile as high formylation degrees were obtained after 1–3 h at room temperature, while either conventional or microwave-assisted heating allowed reduction of the formylation time to 20 min. Copyright © 2017 European Peptide Society and John Wiley & Sons, Ltd." @default.
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• W2605396427 date "2017-04-19" @default.
• W2605396427 modified "2023-10-02" @default.
• W2605396427 title "On-resin N-formylation of peptides: a head-to-head comparison of reagents in solid-phase synthesis of ligands for formyl peptide receptors" @default.
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• W2605396427 doi "https://doi.org/10.1002/psc.2998" @default.
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