Chemistry and Developments of Fluorinated Carbohydrates

Influenza neuraminidase operates via a nucleophilic mechanism and can be targeted by covalent inhibitors

“…Another electronegative group at the C-3 position should also be present to destabilize any oxocarbenium ion transition-state intermediate, thereby stabilizing the potential Tyr406-inhibitor covalent bond 26 . Fluorinated compounds have been investigated for their anti-NA activity for quite some time and are excellent choices for covalent influenza NA inhibitors [26][27][28][29][30] . Although 2b,3eq-difluoro-Neu5Ac, which has been explored as an inhibitor of parainfluenza virus, was readily available from our previous studies 30 , structural analysis clearly demonstrates that the compound should be in the a-anomeric configuration so that the …”

Synthesis, evaluation and molecular docking studies of amino acid derived N-glycoconjugates as antibacterial agents

“…Amino acids and carbohydrates are major constituents of glycoproteins, which acts as hormones, protective agents, structural molecules etc [2][3][4][5][6]. Glycopeptides are well known for its antibiotic and antibacterial activities [7][8][9][10][11][12][13][14]. Recently, we have developed a series of amino acid derived glycoconjugates that exhibit a fair amount of antiinflammatory and analgesic properties [15].…”

Regulation of Heparan Sulfate and Chondroitin Sulfate Glycosaminoglycan Biosynthesis by 4-Fluoro-glucosamine in Murine Airway Smooth Muscle Cells

“…The atomic size of fluorine is only slightly smaller (van der Waals' radius (rЈ) of 135 pm) than that of oxygen (140 pm), and the C-F bond has a higher energy (485 kJ/mol) compared with that of C-O (370 kJ/mol) (5). The substitution of fluorine for oxygen at the 4-position of N-acetylglucosamine (4-F-GlcNAc) 2 confers a greater electronegativity on the bond and makes it less likely to be removed from the GlcN carbon ring.…”