title: Rational design of reversible and irreversible cysteine sulfenic acid-targeted linear C-nucleophiles.
abstract: Concerns about off-target effects has motivated the development of reversible covalent inhibition strategies for targeting cysteine. However, such strategies have not been reported for the unique cysteine oxoform, sulfenic acid. Herein, we have designed and identified linear C-nucleophiles that react selectively with cysteine sulfenic acid. The resulting thioether adducts exhibit reversibility ranging from minutes to days under reducing conditions, showing the feasibility of tuning C-nucleophile reactivity across a wide range of time scales.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, Jupiter, Florida 33458, USA. kcarroll@scripps.edu.
authors.forename: Vinayak
authors.initials: V
authors.lastname: Gupta
authors.affiliation: Department of Chemistry, The Scripps Research Institute, Jupiter, Florida 33458, USA. kcarroll@scripps.edu.
authors.forename: Kate S
authors.initials: KS
authors.lastname: Carroll
mesh_terms: D003545:Cysteine / Q000031:analogs & derivatives* / Q000737:chemistry; D013434:Sulfenic Acids / Q000737:chemistry*
chemical_list: D013434:Sulfenic Acids; C100870:cysteinesulfenic acid; D003545:Cysteine