Importance of Co-operative Hydrogen Bonding in the Apramycin-Ribosomal Decoding A-Site Interaction.
aminoglycoside modifying enzymes
aminoglycosides
antibacterial
antiribosomal activity
hydrogen bonding
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
03 01 2023
03 01 2023
Historique:
revised:
05
10
2022
received:
08
09
2022
pubmed:
6
10
2022
medline:
24
1
2023
entrez:
5
10
2022
Statut:
ppublish
Résumé
An intramolecular hydrogen bond between the protonated equatorial 7'-methylamino group of apramycin and the vicinal axial 6'-hydroxy group acidifies the 6'-hydroxy group leading to a strong hydrogen bond to A1408 in the ribosomal drug binding pocket in the decoding A site of the small ribosomal subunit. In 6'-epiapramycin, the trans-nature of the 6'-hydroxy group and the 7'-methylamino group results in a much weaker intramolecular hydrogen bond, and a consequently weaker cooperative hydrogen bonding network with A1408, resulting overall in reduced inhibition of protein synthesis and antibacterial activity.
Identifiants
pubmed: 36198651
doi: 10.1002/cmdc.202200486
pmc: PMC10092258
doi:
Substances chimiques
apramycin
388K3TR36Z
Anti-Bacterial Agents
0
Nebramycin
11048-13-8
Aminoglycosides
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200486Informations de copyright
© 2022 The Authors. ChemMedChem published by Wiley-VCH GmbH.
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