Synthesis and anti-HIV activity of guanidinoglycosides.
The new guanidinylation reagent N,N'-diBoc-N''-triflylguanidine was used to efficiently convert multiamine-containing glycosides including kanamycin A and B, tobramycin, paromomycin, and neomycin B to the corresponding fully guanidinylated analogues (guanidinoglycosides). This transformation occurs in the presence of H(2)O under mild conditions. Guanidinotobramycin and guanidinoneomycin B were found to inhibit the replication of the HIV virus with activities approximately 100 times greater than the parent aminoglycosides.
Baker
T J
TJ
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093-0343, USA.
Luedtke
N W
NW
Tor
Y
Y
Goodman
M
M
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis*; D006146:Guanidines / Q000138:chemical synthesis*; D006367:HeLa Cells; D006801:Humans; D007202:Indicators and Reagents; D008969:Molecular Sequence Data
D019380:Anti-HIV Agents; D006027:Glycosides; D006146:Guanidines; D007202:Indicators and Reagents