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Synthesis and anti-HIV activity of guanidinoglycosides
T J Baker1, N W Luedtke, Y Tor
1Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093-0343, USA.
Abstract:
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.
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