In-solution direct oxidative coupling for the integration of sulfur/selenium into DNA-encoded chemical libraries

Abstract

Sulfur/selenium-containing electron-rich arenes (ERAs) exist in a wide range of both approved and investigational drugs with diverse pharmacological activities. These unique chemical structures and bioactive properties, if combined with the...

Development of on-DNA vinyl sulfone synthesis for DNA-encoded chemical libraries

“…This indicated that our on-DNA vinyl sulfones could be potentially used in DNA–protein conjugate labelling. 30 Moreover, the sulfide in the thiol adduct product aa36 could be further converted into the corresponding sulfoxide through our previously reported protocol, 31 as shown in Scheme 5b. This chemical transformation provided additional diversification, conceptually in accordance with the DEL technology.…”

Clickable Selenylation – a Paradigm for Seleno‐Medicinal Chemistry

“…Notably, this reaction provides a unique solution to increase the reactivity of highly diluted DNA‐conjugated substrates and abolishes the need of heavy metals from photocatalysts. Recently, Li and coworkers reported an in‐solution oxidative coupling procedure that could efficiently incorporate Se into DNA‐conjugated electron rich arene (ERA) under mild conditions (Figure 3iic) [35] . This method features a transition‐metal free process and a broad scope of Se source, including diselenide, selenol, selenyl chloride, sulfonyl selenol and Ebselen.…”

“…Recently, Li and coworkers reported an in-solution oxidative coupling procedure that could efficiently incorporate Se into DNA-conjugated electron rich arene (ERA) under mild conditions (Figure 3iic). [35] This method features a transition-metal free process and a broad scope of Se source, including diselenide, selenol, selenyl chloride, sulfonyl selenol and Ebselen.…”

DNA-Compatible Suzuki-Miyaura Cross-Coupling Reaction of Aryl Iodides With (Hetero)Aryl Boronic Acids for DNA-Encoded Libraries

“…To expand the chemical space of these DNA-Encoded Libraries, a greater variety of DNA-Compatible reactions is required. Although much progress has been made in this direction ( Potowski et al, 2021 ; Nie et al, 2022 ; Shen et al, 2022 ; Yang et al, 2022 ), the availability of efficient synthetic methods for the synthesis of DELs remains an important challenge.…”