On-DNA sulfonamide and reverse sulfonamide synthesis: (A) on-DNA sulfonamide reaction conditions and reaction scope. a aryl sulfonamide formation, aryl sulfinate (500 mM), iodine (500 mM), in EtOH, 18 h. b alkyl sulfonamide formation: alkyl sulfinate (1000 mM), NCS (500 mM), in EtOH, 1.5 h sonication. (B) reverse sulfonamide formation reaction conditions and reaction scope. c reaction conditions: rongalite (750 mM), DMSO, 18 h. wash with DMSO. amine (500 mM), DCDMH (500 mM), DMSO, 18 hr. (C) proposed RASS enabled workflow for performing multiple encoded diversification steps using a sensitive intermediate.