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. (6th April 2023)

• Record Type: Journal Article
• Authors: Mohamad-Ramshan, Rukshana; Ande, Chennaiah; Matsushita, Takahiko; Haldimann, Klara; Vasella, Andrea; Hobbie, Sven N.; Crich, David
• Is Part Of: Tetrahedron. Volume 135(2023)
• Publication Date: 2023-04-06
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2023.133330
• Languages: English
• ISSNs: 0040-4020

Abstract

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. Graphical abstract: Image 1