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

Mohamad-Ramshan, Rukshana; Ande, Chennaiah; Matsushita, Takahiko; Haldimann, Klara; Vasella, Andrea; Hobbie, Sven N; Crich, David

doi:10.1016/j.tet.2023.133330

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Mohamad-Ramshan, R., Ande, C., Matsushita, T., Haldimann, K., Vasella, A., Hobbie, S. N., & Crich, D. (2023). 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. Tetrahedron, 135, 133330. https://doi.org/10.1016/j.tet.2023.133330

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 confo