Copper-Free Huisgen Cycloaddition for the 14-3-3-Templated Synthesis of Fusicoccin-Peptide Conjugates.
14-3-3
Huisgen cycloaddition
fusicoccin
heteroatom-embedded cycloalkyne
protein-templated reaction
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
16 Mar 2020
16 Mar 2020
Historique:
received:
09
01
2020
pubmed:
6
2
2020
medline:
9
3
2021
entrez:
5
2
2020
Statut:
ppublish
Résumé
Mid-sized molecules have emerged as an attractive chemical space and potentially provide a robust basis for the development of synthetic agents to control intracellular protein interactions. However, the limited cell permeability and chemical tractability of such agents remain to be addressed. We envisioned that target-templated synthesis of such mid-sized molecules might provide a solution. Here, we exploited a copper-free Huisgen cycloaddition for template synthesis using a peptide fragment containing a 4,8-diazacyclononyne (DACN) moiety and an azide-containing fusicoccin derivative in the presence or absence of recombinant 14-3-3ζ protein in vitro. Time-course changes in the yield of products demonstrated that the reaction was accelerated in the presence of 14-3-3 and one of the regioisomers was generated predominantly, supporting the template effect.
Identifiants
pubmed: 32017414
doi: 10.1002/asia.202000042
doi:
Substances chimiques
14-3-3 Proteins
0
Azides
0
Glycosides
0
Peptides
0
fusicoccin
20108-30-9
Copper
789U1901C5
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
742-747Subventions
Organisme : Japan Society for the Promotion of Science
ID : 19K15567
Organisme : Japan Society for the Promotion of Science
ID : 18H02106
Organisme : Japan Society for the Promotion of Science
ID : 16K13098
Organisme : Ministry of Education, Culture, Sports, Science and Technology
ID : 18H04419
Organisme : Ministry of Education, Culture, Sports, Science and Technology
ID : 18H04394
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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These products were determined as either isomers by 1H NMR and HRMS. NOE measurement under heating condition did not detect apparent signals, and at present the regiochemistry is not yet determined.
DFT calculations for cycloaddition of NMs,N′Ac-DACN with phenyl azide were performed at B3LYP/6-311G(d p) level of theory as a model reaction to set the criteria for 4-1TS′ and 4-2TS′ (see S. I.).