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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.

SUBMITTER: Mohamad-Ramshan R

PROVIDER: S-EPMC10081503 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

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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 R Ande Chennaiah C Matsushita Takahiko T Haldimann Klara K Vasella Andrea A Hobbie Sven N SN Crich David D

Tetrahedron 20230223

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, perha ...[more]

PMID: 37035443

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