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Updated: May 31, 2025

Metabolic Pathway Confirmation and Discovery Through 13C-labeling of Proteinogenic Amino Acids
Published on: January 26, 2012
Catalytic Serine Labeling in Nonaqueous, Acidic Media
Seiya Ishizawa1, Chiamaka P Uzoewulu1, Yume Iwakura1
1Department of Chemistry, North Carolina State University, Raleigh, North Carolina, 27695, United States.
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.
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