Towards DNA-Encoded Micellar Chemistry: DNA-Micelle Association and Environment Sensitivity of Catalysis.
DNA conjugates
copolymers
heterocycle synthesis
micellar catalysis
partitioning
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
12 Jul 2021
12 Jul 2021
Historique:
received:
17
03
2021
pubmed:
13
5
2021
medline:
16
7
2021
entrez:
12
5
2021
Statut:
ppublish
Résumé
The development of DNA-compatible reaction methodologies is a central theme to advance DNA-encoded screening library technology. Recently, we were able to show that sulfonic acid-functionalized block copolymer micelles facilitated Brønsted acid-promoted reactions such as the Povarov reaction on DNA-coupled starting materials with minimal DNA degradation. Here, the impact of polymer composition on micelle shape, and reaction conversion was investigated. A dozen sulfonic acid-functionalized block copolymers of different molar mass and composition were prepared by RAFT polymerization and were tested in the Povarov reaction, removal of the Boc protective group, and the Biginelli reaction. The results showed trends in the polymer structure-micellar catalytic activity relationship. For instance, micelles composed of block copolymers with shorter acrylate ester chains formed smaller particles and tended to provide faster reaction kinetics. Moreover, fluorescence quenching experiments as well as circular dichroism spectroscopy showed that DNA-oligomer-conjugates, although highly water-soluble, accumulated very effectively in the micellar compartments, which is a prerequisite for carrying out a DNA-encoded reaction in the presence of polymer micelles.
Identifiants
pubmed: 33979454
doi: 10.1002/chem.202100980
pmc: PMC8361662
doi:
Substances chimiques
Micelles
0
Polymers
0
DNA
9007-49-2
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
10048-10057Subventions
Organisme : EFRE-NRW
ID : EFRE-NRW-funded Patent Validation Grant
Organisme : EFRE-NRW
ID : EFRE-NRW-funded Drug Discovery Hub Dortmund (DDHD)
Organisme : DFG
ID : EXC 2033 - 390677874 - RESOLV
Informations de copyright
© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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