Premium
Tetrafluorination of Sugars as Strategy for Enhancing Protein–Carbohydrate Affinity: Application to UDP‐Gal p Mutase Inhibition
Author(s) -
N'Go Inès,
Golten Samuel,
Ardá Ana,
Cañada Javier,
JiménezBarbero Jesús,
Linclau Bruno,
Vincent Stéphane P.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303693
Subject(s) - mutase , biochemistry , chemistry , enzyme , sugar , mycobacterium tuberculosis , tuberculosis , medicine , pathology
Tetrafluorinated analogues of both UDP‐galactopyranose and UDP‐galactofuranose have been synthesized and assayed against UDP‐galactopyranose mutase, a key enzyme for Mycobacterium tuberculosis cell wall biosynthesis. Competition assays and STD‐NMR spectroscopy techniques have evidenced not only the first unambiguous case of affinity enhancement through local sugar polyfluorination, but also showed that tetrafluorination can still have a beneficial effect on binding when monofluorination at the same position does not.