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On-Demand Detachment of Succinimides on Cysteine to Facilitate (Semi)Synthesis of Challenging Proteins

Ganga B. Vamisetti, Gandhesiri Satish, Prasad Sulkshane, Guy Mann, Michael H. Glickman, Ashraf Brik

2020Journal of the American Chemical Society48 citationsDOIOpen Access PDF

Abstract

was applied for the synthesis of two ubiquitin activity-based probes (Ub-ABPs) employing solid phase chemical ligation (SPCL). SPCL was achieved through a sequential three segment ligation on a polymer support via a maleimide anchor. The obtained probes successfully formed the expected covalent complexes with deubiquitinating enzymes (DUBs) USP2 and USP7, highlighting the use of our new method for efficient preparation of unique synthetic proteins. Importantly, we demonstrate the advantages of our newly developed method for the protection and deprotection of native cysteine with a succinimide group in a peptide fragment derived from thioredoxin-1 (Trx-1) obtained via intein based expression to enable ligation/desulfurization and subsequent disulfide bond formation in a one-pot process.

Topics & Concepts

ChemistrySuccinimidesCysteineOn demandCombinatorial chemistryComputational biologyBiochemistryOrganic chemistryEnzymeBiologyMultimediaComputer scienceChemical Synthesis and AnalysisClick Chemistry and ApplicationsBiochemical and Structural Characterization
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