Rapid sodium periodate cleavage of an unnatural amino acid enables unmasking of a highly reactive α-oxo aldehyde for protein bioconjugation
Robin Brabham, Tessa Keenan, Annika Hüsken, Jacob Bilsborrow, Ryan McBerney, Vajinder Kumar, W. Bruce Turnbull, Martin A. Fascione
Abstract
The α-oxo aldehyde is a highly reactive aldehyde for which many protein bioconjugation strategies exist. Here, we explore the genetic incorporation of a threonine-lysine dipeptide into proteins, harbouring a "masked"α-oxo aldehyde that is rapidly unveiled in four minutes. The reactive aldehyde could undergo site-specific protein modification by SPANC ligation.
Topics & Concepts
ChemistryBioconjugationSodium periodateCleavage (geology)AldehydeAmino acidPeriodateBiochemistryCombinatorial chemistryOrganic chemistryGeotechnical engineeringCatalysisFracture (geology)EngineeringChemical Synthesis and AnalysisClick Chemistry and ApplicationsFluorine in Organic Chemistry