Translation of the copper/bipyridine-promoted Petasis reaction to solid phase-coupled DNA for encoded library synthesis.
DNA-encoded library
Encoded chemistry
Multicomponent reaction
Petasis reaction
α-aryl glycines
Journal
Bioorganic & medicinal chemistry
ISSN: 1464-3391
Titre abrégé: Bioorg Med Chem
Pays: England
ID NLM: 9413298
Informations de publication
Date de publication:
01 05 2020
01 05 2020
Historique:
received:
17
01
2020
revised:
28
02
2020
accepted:
12
03
2020
pubmed:
31
3
2020
medline:
29
5
2021
entrez:
31
3
2020
Statut:
ppublish
Résumé
The Petasis three-component reaction gives rise to diverse substituted α-aryl glycines from readily available amines, boronic acids and glyoxalic acid. Thus, this reaction is highly attractive for DNA-encoded small molecule screening library synthesis. The Petasis reaction is for instance promoted by a potentially DNA damaging copper(I)/bipyridine reagent system in dry organic solvents. We found that solid phase-coupled DNA strands tolerated this reagent system at elevated temperature allowing for synthesis of diverse substituted DNA-tagged α-aryl glycines from DNA-conjugated secondary amines.
Identifiants
pubmed: 32222338
pii: S0968-0896(20)30251-0
doi: 10.1016/j.bmc.2020.115441
pii:
doi:
Substances chimiques
Pyridines
0
Small Molecule Libraries
0
Copper
789U1901C5
DNA
9007-49-2
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
115441Informations de copyright
Copyright © 2020 Elsevier Ltd. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of Competing Interest The authors declared that there is no conflict of interest.