A biotin labeling probe featuring an acid-cleavable dialkoxydiphenylsilane (DADPS) linker, a picolyl azide reactive group, and a biotin affinity tag. The picolyl azide undergoes copper-catalyzed azide-alkyne cycloaddition (CuAAC) with alkyne-tagged biomolecules, with the picolyl group accelerating the ligation through copper chelation. Designed for chemical proteomics and metabolic labeling workflows, this probe enables streptavidin-based enrichment of click-tagged targets followed by mild acid cleavage of the DADPS linker to release captured biomolecules under gentle conditions.