Synthesis of 4-O-(4-Amino-4-deoxy-β-D-xylopyranosyl)paromomycin and 4-S-(β-D-Xylopyranosyl)-4-deoxy-4'-thio-paromomycin and Evaluation of their Antiribosomal and Antibacterial Activity

Abstract

The design, synthesis and antiribosomal and antibacterial activity of two novel glycosides of the aminoglycoside antibiotic paromomycin are described. The first carries of 4-amino-4-deoxy-β-D-xylopyranosyl moiety at the paromomycin 4'-position and is approximately two-fold more active than the corresponding β-D-xylopyranosyl derivative. The second is a 4'-(β-D-xylopyranosylthio) derivative of 4'-deoxyparomomycin that is unexpectedly less active than the simple β-D-xylopyranosyl derivative, perhaps because of the insertion of the conformationally more mobile thioglycosidic linkage.