Synthesis, docking study and biological evaluation of ᴅ-fructofuranosyl and ᴅ-tagatofuranosyl sulfones as potential inhibitors of the mycobacterial galactan synthesis targeting the galactofuranosyltransferase GlfT2

Autor: Marek Baráth, Jana Jakubčinová, Zuzana Konyariková, Stanislav Kozmon, Katarína Mikušová, Maroš Bella
Jazyk: angličtina
Rok vydání: 2020
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 16, Iss 1, Pp 1853-1862 (2020)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.16.152
Popis: A series of ten novel ᴅ-fructofuranosyl and ᴅ-tagatofuranosyl sulfones bearing a 1-O-phosphono moiety and three different substituents at C-2 has been prepared. Due to the structural similarities of these scaffolds to the native substrate of mycobacterial galactofuranosyltransferase GlfT2 in the transition state, we evaluated these compounds by computational methods, as well as in an enzyme assay for the possible inhibition of the mycobacterial galactan biosynthesis. Our data show that despite favorable docking scores to the active site of GlfT2, none of these compounds serve as efficient inhibitors of the enzymes involved in the mycobacterial galactan biosynthesis.
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