Synthesis and anti-HIV activity of guanidinoglycosides |
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Authors: | Baker T J Luedtke N W Tor Y Goodman M |
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Institution: | Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093-0343, USA. |
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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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