Yuting Gao,Yue Fang,Chang Chen,Xianfeng Li,Xianfu Fang,Yangfeng Li,Yizhou Li

Organic Letters

DOI: 10.1021/acs.orglett.6c02361

Abstract

Epoxides are valuable electrophilic warheads for covalent DNA-encoded libraries (CoDELs), yet their incorporation remains constrained by limited on-DNA-generation methods. Herein, we report an efficient on-DNA functional group transformation for alkene epoxidation. The resulting DNA-conjugated epoxides serve as versatile warheads and intermediates, enabling downstream diversification via ring-opening reactions with amines and thiols. Given its excellent DNA compatibility, this strategy significantly expands the chemical space accessible to both CoDELs and the broader DEL field.