# Diverse Library of 5a-Substituted Carba-Glucosamines

## TL;DR

Scientists created a diverse set of carba-glucosamine compounds that can act as antibiotics by targeting bacterial cell wall synthesis.

## Contribution

A new library of 20 carba-glucosamine derivatives with varied substituents was synthesized and tested for antibacterial activity.

## Key findings

- The compounds were efficiently synthesized from late-stage intermediates.
- Some carba-glucosamine derivatives showed promising antibacterial activity against Bacillus subtilis in a filter disk assay.

## Abstract

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 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 disk
assay.