Step-economy synthesis of β-steryl sialosides using a sialyl iodide donor.


University of California, Davis, One Shields Avenue, Davis, CA, 95616, USA. [Email]


Steryl glycosides are prevalent in nature and have unique biological activities dictated by sterol structure, sugar composition, and the stereochemical attachment of the aglycone. A single configurational switch can have profound biological consequences meriting the systematic study of structure and function relationships. Steryl congeners of N-acetyl neuraminic acid (NANA) impact neurobiological processes and may also mediate host/microbe interactions. In order to study these processes, a platform for the synthesis of β-steryl sialosides has been established. Promoter-free glycosidations using a novel α-linked sialyl iodide donor efficiently provide unique amphiphilic sialoglycoconjugates for examining bioactivities in various systems.

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