SYNTHESIS AND INFLUENZA-VIRUS SIALIDASE INHIBITORY ACTIVITY OF THE 5-DESACETAMIDO ANALOG OF EHYDRO-2,4-DIDEOXY-4-GUANIDINYL-N-ACETYLNEURAMINIC ACID (GG167)

Authors
STARKEY ID MAHMOUDIAN M NOBLE D SMITH PW CHERRY PC HOWES PD SOLLIS SL
Citation
Id. Starkey et al., SYNTHESIS AND INFLUENZA-VIRUS SIALIDASE INHIBITORY ACTIVITY OF THE 5-DESACETAMIDO ANALOG OF EHYDRO-2,4-DIDEOXY-4-GUANIDINYL-N-ACETYLNEURAMINIC ACID (GG167), Tetrahedron letters, 36(2), 1995, pp. 299-302
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
2
Year of publication
1995
Pages
299 - 302
Database
ISI
SICI code
0040-4039(1995)36:2<299:SAISIA>2.0.ZU;2-C
Abstract
The title compound 2b has been synthesised in 8 steps from 2-deoxy-D-g lucose (2-DG). Key transformations were an aldolase reaction utilising 2-DG to form the 9 carbon sugar 3, and then introduction of the requi red unsaturation and a 4-amino substituent in a one-pot process. The p oor inhibitory activity of 2b demonstrates that the 5-acetamido substi tuent in ehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid(GG167 ) 1 is critical for sialidase binding.