Abstract
THE conversion of dihydrostreptomycin (DHSM) to dideguanyldihydrostreptomycin (DGSM) has been described1. In the DGSM molecule, the two guanidino groups of DHSM have been converted to primary amino groups with no other detectable structural change. The primary amino groups of DGSM were found to be weaker in basicity pK about 6.3) than the secondary amino group of the molecule (pK, 7.9) (ref. 1). The net charge on the DGSM molecule at pH 7.0 in aqueous media thus would be expected to be +1, compared with a net charge of +3 for the parent molecule-DHSM. DGSM had no biological activity when assayed by conventional techniques, with streptomycin-sensitive and dependent Escherichia coli.
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References
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POLGLASE, W. Contribution of the Cationic Groups of Dihydrostreptomycin to Biological Activity. Nature 206, 298–299 (1965). https://doi.org/10.1038/206298b0
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DOI: https://doi.org/10.1038/206298b0
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