Synthesis of delta4-beta-D-glucopyranosiduronic acids as mimetics of 2,3-unsaturated sialic acids for sialidase inhibition.
Mimetics of Neu5Ac2en and KDN2en, based on delta4-beta-delta-glucopyranosiduronic acids, have been synthesised. The Neu5Ac2en mimetic 5 showed inhibition of both bacterial and viral sialidases, with inhibition of the viral sialidase being comparable to that of Neu5Ac2en itself.
Florio
P
P
Department of Medicinal Chemistry, Monash University (Parkville Campus), Victoria, Australia.
Thomson
R J
RJ
Alafaci
A
A
Abo
S
S
von Itzstein
M
M
D000818:Animals; D004353:Drug Evaluation, Preclinical; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D005965:Glucuronates / Q000138:chemical synthesis* / Q000494:pharmacology*; D009980:Influenza A virus / Q000201:enzymology; D018716:Molecular Mimicry; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives / Q000737:chemistry; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D010125:Ostreidae / Q000201:enzymology; D012486:Salmonella typhimurium / Q000201:enzymology; D012794:Sialic Acids / Q000737:chemistry / Q000378:metabolism; D013329:Structure-Activity Relationship; D014734:Vibrio cholerae / Q000201:enzymology
C105090:2-deoxy-2,3-didehydro-D-glycero-D-galacto-2-nonulopyranosonic acid; D004791:Enzyme Inhibitors; D005965:Glucuronates; D012794:Sialic Acids; C036137:2-deoxy-2,3-dehydro-N-acetylneuraminic acid; D009439:Neuraminidase; D019158:N-Acetylneuraminic Acid