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• W4308394098 abstract "Abstract Chemical synthesis of proteins bearing base‐labile post‐translational modifications (PTMs) is a challenging task. For instance, O ‐acetylation and S ‐palmitoylation PTMs cannot survive Fmoc removal conditions during Fmoc‐solid phase peptide synthesis (SPPS). In this work, we developed a new Boc‐SPPS‐based strategy for the synthesis of peptide C‐terminal salicylaldehyde (SAL) esters, which are the key reaction partner in Ser/Thr ligation and Cys/Pen ligation. The strategy utilized the semicarbazone‐modified aminomethyl (AM) resin, which could support the Boc‐SPPS and release the peptide SAL ester upon treatment with TFA/H 2 O and pyruvic acid. The non‐oxidative aldehyde regeneration was fully compatible with all the canonical amino acids. Armed with this strategy, we finished the syntheses of the O ‐acetylated protein histone H3(S10ac, T22ac) and the hydrophobic S ‐palmitoylated peptide derived from caveolin‐1." @default.
• W4308394098 created "2022-11-11" @default.
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• W4308394098 date "2022-11-30" @default.
• W4308394098 modified "2023-10-15" @default.
• W4308394098 title "Chemical Synthesis of Proteins with Base‐Labile Posttranslational Modifications Enabled by a Boc‐SPPS Based General Strategy Towards Peptide C‐Terminal Salicylaldehyde Esters" @default.
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• W4308394098 doi "https://doi.org/10.1002/ange.202214053" @default.
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