Work

Diverse Library of 5a-Substituted Carba-Glucosamines

Year: 2025

Type: article

Abstract: Carba-sugars – carbohydrate mimics in which the ring oxygen is replaced by a methylene group – are carbohydrate analogs of natural or synthetic origin that can have important biological functions. Especially, carba-aminosugars and glycosides containing carba-aminosugars are potent antibiotics. Furthermore, they have been shown to induce the self-cleavage reaction of the glmS riboswitch and thereby inhibit the ability of bacteria to synthesize glucosamine-6-phosphate, which is required to build up the bacterial cell wall. We report the synthesis of a library of 20 carba-glucosamine derivatives with various substituents at the carba-position including amines, alkyl, alkoxy, and aryloxy derivatives, fluorine derivatives, glycosylated derivatives and a cyclopropane derivative. The compounds were obtained in an efficient way starting from late-stage synthetic intermediates of an earlier developed synthesis of carba-substituted carba-glucosamines. All carba-glucosamine mimics were tested for their antibacterial properties against Bacillus subtilis and some of them displayed promising activities in a filter disc assay.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c02816

Authors: Bjarne Silkenath, Dennis Kläge, Philip Eppelin, Jörg S. Hartig, Valentin Wittmann

Institution: University of Konstanz

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Deutsche Forschungsgemeinschaft, Universität Konstanz