A Rapid and Efficient Building Block Approach for Click Cyclization of Peptoids.
click chemistry
peptide backbone modification
peptide cyclization
peptide-peptoid hybrids
peptides
peptoids
Journal
Frontiers in chemistry
ISSN: 2296-2646
Titre abrégé: Front Chem
Pays: Switzerland
ID NLM: 101627988
Informations de publication
Date de publication:
2020
2020
Historique:
received:
03
02
2020
accepted:
17
04
2020
entrez:
9
6
2020
pubmed:
9
6
2020
medline:
9
6
2020
Statut:
epublish
Résumé
Cyclic peptide-peptoid hybrids possess improved stability and selectivity over linear peptides and are thus better drug candidates. However, their synthesis is far from trivial and is usually difficult to automate. Here we describe a new rapid and efficient approach for the synthesis of click-based cyclic peptide-peptoid hybrids. Our methodology is based on a combination between easily synthesized building blocks, automated microwave assisted solid phase synthesis and bioorthogonal click cyclization. We proved the concept of this method using the INS peptide, which we have previously shown to activate the HIV-1 integrase enzyme. This strategy enabled the rapid synthesis and biophysical evaluation of a library of cyclic peptide-peptoid hybrids derived from HIV-1 integrase in high yield and purity. The new cyclic hybrids showed improved biological activity and were significantly more stable than the original linear INS peptide.
Identifiants
pubmed: 32509731
doi: 10.3389/fchem.2020.00405
pmc: PMC7248394
doi:
Types de publication
Journal Article
Langues
eng
Pagination
405Informations de copyright
Copyright © 2020 Samarasimhareddy, Shamir, Shalev, Hurevich and Friedler.
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