An efficient synthesis of 1,6-anhydro- N-acetylmuramic acid from N-acetylglucosamine

Matthew B Calvert; Christoph Mayer; Alexander Titz

doi:10.3762/bjoc.13.261

An efficient synthesis of 1,6-anhydro- N-acetylmuramic acid from N-acetylglucosamine

Beilstein J Org Chem. 2017 Dec 11:13:2631-2636. doi: 10.3762/bjoc.13.261. eCollection 2017.

Authors

Matthew B Calvert^{1

2}, Christoph Mayer³, Alexander Titz^{1

2

4}

Affiliations

¹ Chemical Biology of Carbohydrates, Helmholtz Institute for Pharmaceutical Research Saarland (HIPS), D-66123 Saarbrücken, Germany.
² Deutsches Zentrum für Infektionsforschung (DZIF), Standort Hannover-Braunschweig, Germany.
³ Interfaculty Institute of Microbiology and Infection Medicine Tübingen (IMIT), Department of Microbiology and Biotechnology, University of Tübingen, Germany.
⁴ Department of Pharmacy, Saarland University, Saarbrücken, Germany.

Abstract

A novel synthesis of 1,6-anhydro-N-acetylmuramic acid is described, which proceeds in only five steps from the cheap starting material N-acetylglucosamine. This efficient synthesis should enable future studies into the importance of 1,6-anhydromuramic acid in bacterial cell wall recycling processes.

Keywords: N-acetylmuramic acid; anhydrosugars; antibiotic resistance; bacterial cell wall recycling; carbohydrate synthesis.