Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 22, Pages 8485-8493Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo030203g
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Funding
- NIGMS NIH HHS [GM60938] Funding Source: Medline
- PHS HHS [46462] Funding Source: Medline
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Four glycodendrons and a glycocluster were synthesized fromcarbohydrate building blocks to form paucivalent (di- to tetravalent) structures of controlled scaffold architectures. Enzymatic sialylation of the functionalized cluster and dendrons, terminated in lactose residues, generated a library of paucivalent synthetic sialosides displaying sialic acids with different dispositions. These newly constructed bioactive sialic acid-based structures were differentially recognized by sialoadhesin, a mammalian macrophage sialic acid binding protein. The binding of the sialosides to sialoadhesin was evaluated by an enzyme-linked immunosorbant assay to investigate the complementarity of scaffold structure and binding to sialoadhesin. Modulating the interaction between sialoadhesin and its sialic acid ligands has important implications in immunobiology.
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