1-N-ACYLATION OF GENTAMICIN C1a, BY A CYCLIC, CHIRAL ;--AMINO-a-HYDROXY ACID RELATED TO THE (S)-4-AMINO-2-HYDROXYBUTYRIC ACID
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چکیده
A semisynthetic aminoglycoside antibiotic 15, containing a cyclic r-amino-a-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 C,a, (12) was condensed with the phtalimido active ester 10 to give after catalytic reduction and deprotection, the hitherto unknown 1-N-substituted gentamicin C,a 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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تاریخ انتشار 2006