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

Tetrahedron. 2023 Apr 6;135:133330. doi: 10.1016/j.tet.2023.133330. Epub 2023 Feb 23.ABSTRACTThe 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.PMID:37035443 | PMC:PMC10081503 | DOI:10.1016/j.tet.2023.133330

Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Rukshana Mohamad-Ramshan Chennaiah Ande Takahiko Matsushita Klara Haldimann Andrea Vasella Sven N Hobbie David Crich Source Type: research