Oral Presentation Royal Australian Chemical Institute National Congress 2026

A CONCISE SYNTHESIS OF AN L-ALTRURONIC ACID GLYCOSYL DONOR (136444)

Ajay Sharma S 1 , Vito Ferro 1 , Nicholas See 1 , Elizabeth Krenske 1
  1. The University of Queensland, Robertson, QUEENSLAND, Australia

 

L-Altruronic acid (L-AltA) is a rare hexose that manifests in the capsular polysaccharides of numerous pathogenic bacteria, including Enterococcus faecium. Encouraging evidence has been provided for the efficacy of glycoconjugates as vaccine candidates against E. faecium. Of those examined, the highest-performing structure contained L-AltA as a signature sugar. However, further investigation in this area has been limited by poor synthetic access to appropriate L-AltA building blocks. We now report the straightforward preparation of a glycosyl donor-functionalized derivative of L-AltA from inexpensive starting materials. Central to this synthesis is the fluorine-directed C-5 epimerization, which has previously been instrumental in accessing other rare L-hexoses.1-3

 

 

  1. 1. N.W. See, N. Wimmer, E.H. Krenske, V. Ferro, Eur. J. Org. Chem., 2021, 1575-1584. 2. N.W. See, G.K. Pierens, E.H. Krenske, V. Ferro, Synthesis, 2024, 56, 966-974. 3. N.W. See, N. Wimmer, G. Zhang, E.H. Krenske, V. Ferro, J. Org. Chem., 2024, 89, 17941-17949.