DOI: 10.1021/acs.joc.6c02197 ISSN: 0022-3263
A Concise Synthesis of
l
-Altruronic Acid: A Rare Sugar Located in the Surface Antigen of
Enterococcus faecium
Nicholas W. See, Ajay Sharma S., Guoqing Zhang, Norbert Wimmer, Elizabeth H. Krenske, Vito Ferro Abstract
l-Altruronic acid-based glycoconjugates demonstrate excellent preliminary efficacy as antigens for Enterococcus faecium vaccine development; however, progress has been limited by the poor accessibility of l-altruronic acid. We report here on a concise preparation of a donor-functionalized derivative of l-altruronic acid via a fluorine-directed C-5 epimerization. DFT calculations also reveal how the stereoselectivity of epimerization is influenced by stabilizing effects in the intermediate carbohydrate radicals.