AI Article Synopsis
- A new semisynthetic aminoglycoside antibiotic, 15, has been developed, featuring a unique cyclic gamma-amino-alpha-hydroxy acid similar to key components of other antibiotics like butirosins and amikacin.
- The synthesis involved condensing a protected form of gentamicin C1a with an active ester, followed by catalytic reduction and deprotection to create this novel compound.
- The side chain necessary for the antibiotic was synthesized from D-(-)-quinic acid, and the study also presents the antibacterial properties of the new compound 15.
Article Abstract
A semisynthetic aminoglycoside antibiotic 15, containing a cyclic gamma-amino-alpha-hydroxy acid, related to the 1-N-4-amino-2-hydroxybutyric acid (AHBA) side chain of butirosins and amikacin, has been prepared. Conveniently protected 3,2',6'-tris-N-tert-butoxycarbonylgentamicin C1a (12) was condensed with the phtalimido active ester 10 to give after catalytic reduction and deprotection, the hitherto unknown 1-N-substituted gentamicin C1a 15. The requisite side chain was synthesized from the readily available D-(-)-quinic acid. The antibacterial properties of 15 are given.
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| http://dx.doi.org/10.7164/antibiotics.35.1507 | DOI Listing |
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