Catalytic Serine Labeling in Nonaqueous, Acidic Media

2025/01/22 by Seiya Ishizawa, Chiamaka Peace Uzoewulu, Yume Iwakura +3 · 1 voice
Biochemistry, Genetics and Molecular Biology · Chemistry · Medicine · #Chemical Synthesis and Analysis #Click Chemistry and Applications #Peptidase Inhibition and Analysis

paper · pdf · doi:10.1002/chem.202404002

openalex publication_date 2025/01/22 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/04

Abstract

Chemoselective modification of alkyl alcohols (e. g., serine residues) on proteins has been a daunting challenge especially in aqueous media. Herein, we report chemical modification of alkyl alcohols in protein and cell lysate samples using carboxylic acid-based bioconjugation media. The acidic medium is not only useful to suppress reactivity of other nucleophiles in proteins, but the medium also serves as a potentially biomolecule-compatible solvent. The acid-catalyzed acylation strategy has a unique selectivity paradigm compared to the common active-serine-targeted method and would act as a new strategy for studying biological roles of serine residues.

Citations

• The logic of protein post‐translational modifications (PTMs): Chemistry, mechanisms and evolution of protein regulation through covalent attachments

Cited by

• Catalysis in Chemical Modification of Proteins

Discussions

• Serine has diverse roles in living systems, but development of serine labeling tools has been a challenge. Our work published @ChemEurJ achieved chemoselective serine acylation in an unbiased manner! [bsky, 0 points, 0 comments]

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