biostudies-literatureUnknown90(8)Silkenath BCarba-sugars─carbohydrate mimics in which the ring oxygen is replaced by a methylene group─are carbohydrate analogues 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 <i>glmS</i> 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 compouThe Journal of organic chemistry2969-2977https://www.ebi.ac.uk/biostudies/studies/S-EPMC11877516biostudies-literatureDiverse Library of 5a-Substituted Carba-Glucosamines.PMC11877516Silkenath BHartig JSWittmann VKlage DEppelin PfalseDiverse Library of 5a-Substituted Carba-Glucosamines.Carba-sugars─carbohydrate mimics in which the ring oxygen is replaced by a methylene group─are carbohydrate analogues 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 <i>glmS</i> 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 compou2025-01-01T00:00:00Z2025 Feb2025-04-18T13:04:02.924Z2025-04-06T22:35:03.32ZS-EPMC118775163995426310.1021/acs.joc.4c02816