Rapid access to uronic acid-based mimetics of Kdn2en from D-glucurono-6,3-lactone.
A concise route to novel mimetics of Kdn2en, based on delta4-uronic acids, from D-glucurono-6,3-lactone is presented. Uronic acid-based mimetics in which an aliphatic ether (O-glycoside), a thioether (S-glycoside), or acetamide takes the place of the natural C-6 glycerol sidechain of the sialic acid were synthesized from the key intermediate, methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate bromide.
Florio
P
P
Department of Medicinal Chemistry, Monash University, Parkville, Vic., Australia.
Thomson
R J
RJ
von Itzstein
M
M
D005965:Glucuronates / Q000737:chemistry; D018716:Molecular Mimicry; D015394:Molecular Structure; D012794:Sialic Acids / Q000737:chemistry*; D014574:Uronic Acids / Q000138:chemical synthesis*
C105090:2-deoxy-2,3-didehydro-D-glycero-D-galacto-2-nonulopyranosonic acid; D005965:Glucuronates; D012794:Sialic Acids; D014574:Uronic Acids; C004940:glucuronolactone