Synthesis of lactose-based S-linked sialylmimetics of alpha(2,3)-sialosides.
[reaction: see text] A new approach toward the synthesis of lactose-based S-linked sialylmimetics of alpha(2,3)-linked sialosides is described. These compounds, represented by the general structure 3, were prepared from methyl beta-d-lactoside in 11 steps. It was found that the choice of protecting group was crucial to allow the efficient introduction of sulfur at the 3-position of the galactose ring.
Liakatos
Angela
A
Institute for Glycomics, Griffith University, Gold Coast Campus, PMB 50 Gold Coast Mail Centre, Queensland 9726, Australia.
Kiefel
Milton J
MJ
von Itzstein
Mark
M
D007785:Lactose / Q000737:chemistry*; D018716:Molecular Mimicry; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*
D019158:N-Acetylneuraminic Acid; D007785:Lactose