Isocyanide Multicomponent Reactions on Solid-Phase-Coupled DNA Oligonucleotides for Encoded Library Synthesis.

Combinatorial Chemistry Techniques Cyanides / chemistry DNA / chemistry Molecular Structure Oligonucleotides / chemistry Solid-Phase Synthesis Techniques

Journal

Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393

Informations de publication

Date de publication:
20 09 2019
Historique:
pubmed: 30 8 2019
medline: 29 7 2020
entrez: 30 8 2019
Statut: ppublish

Résumé

Isocyanide multicomponent reactions play a prominent role in drug discovery. This chemistry has hardly been investigated for compatibility with DNA-encoded combinatorial synthesis. The Ugi, Ugi-azide, and Groebke-Blackburn-Bienaymé reactions are well-tolerated by DNA on the solid phase and show a broad scope. However, an oxadiazole-forming variant of the Ugi reaction caused DNA depurination, requiring a more stable hexathymidine DNA for encoded library synthesis. Cheminformatic analysis revealed that isocyanide multicomponent-reaction-based encoded libraries cover a diverse chemical space.

Identifiants

DOI: 10.1021/acs.orglett.9b02448 PMID: 31464126
pubmed: 31464126
doi: 10.1021/acs.orglett.9b02448
doi:

Substances chimiques

Cyanides 0
Oligonucleotides 0
DNA 9007-49-2

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

7238-7243

Auteurs

Verena B K Kunig (VBK)

Faculty of Chemistry and Chemical Biology , TU Dortmund University , Otto-Hahn-Straße 6 , 44227 Dortmund , Germany.

Christiane Ehrt (C)

Faculty of Chemistry and Chemical Biology , TU Dortmund University , Otto-Hahn-Straße 6 , 44227 Dortmund , Germany.

Alexander Dömling (A)

Drug Design , University of Groningen , Deusinglaan 1 , 7313 AV Groningen , The Netherlands.
ORCID: 0000-0002-9923-8873

Andreas Brunschweiger (A)

Faculty of Chemistry and Chemical Biology , TU Dortmund University , Otto-Hahn-Straße 6 , 44227 Dortmund , Germany.
ORCID: 0000-0002-4401-1495

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Classifications MeSH

questionsmedicales.fr › Technologie, industrie et agriculture › Technologie › Technologie pharmaceutique › Techniques de chimie synthétique › Techniques de chimie combinatoire › Isocyanide Multicomponent Reactions on...
questionsmedicales.fr › Produits chimiques inorganiques › Composés de l'azote › Acide cyanhydrique › Cyanures › Isocyanide Multicomponent Reactions on...
questionsmedicales.fr › Acides nucléiques, nucléotides et nucléosides › Acides nucléiques › ADN › Isocyanide Multicomponent Reactions on...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Isocyanide Multicomponent Reactions on...
questionsmedicales.fr › Acides nucléiques, nucléotides et nucléosides › Nucléotides › Polynucléotides › Oligonucléotides › Isocyanide Multicomponent Reactions on...
questionsmedicales.fr › Technologie, industrie et agriculture › Technologie › Technologie pharmaceutique › Techniques de chimie synthétique › Techniques de synthèse en phase solide › Isocyanide Multicomponent Reactions on...