sp3 -Rich Heterocycle Synthesis on DNA: Application to DNA-Encoded Library Production.
Angew Chem Int Ed Engl
; 63(12): e202319836, 2024 Mar 18.
Article
en En
| MEDLINE
| ID: mdl-38330151
ABSTRACT
DNA encoded library (DEL) synthesis represents a convenient means to produce, annotate and store large collections of compounds in a small volume. While DELs are well suited for drug discovery campaigns, the chemistry used in their production must be compatible with the DNA tag, which can limit compound class accessibility. As a result, most DELs are heavily populated with peptidomimetic and sp2 -rich molecules. Herein, we show that sp3 -rich mono- and bicyclic heterocycles can be made on DNA from ketochlorohydrin aldol products through a reductive amination and cyclization process. The resulting hydroxypyrrolidines possess structural features that are desirable for DELs and target a distinct region of pharmaceutically relevant chemical space.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
ADN
/
Bibliotecas de Moléculas Pequeñas
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Año:
2024
Tipo del documento:
Article
País de afiliación:
Suiza