Optimizations of Lipid II Synthesis: An Essential Glycolipid Precursor in Bacterial Cell Wall Synthesis and a Validated Antibiotic Target

Submitting author affiliation:
Queen's University Belfast, Belfast, United Kingdom

Beilstein Arch. 2023, 202349. https://doi.org/10.3762/bxiv.2023.49.v1

Published 21 Nov 2023

cc-by Logo


Lipid II is an essential glycolipid found in bacteria. Accessing this valuable cell wall precursor is important both for studying cell wall synthesis and for studying/identifying novel antimicrobial compounds. Herein we describe optimizations to the modular chemical synthesis of lipid II and unnatural analogues. In particular, the glycosylation step, a critical step in the formation of the central disaccharide unit (GlcNAc-MurNAc), was optimized. This was achieved by employing the use of glycosyl donors with diverse leaving groups. The key advantage of this approach lies in its adaptability, allowing for the generation of a wide array of analogues through the incorporation of alternative building blocks at different stages of synthesis.

Keywords: Chemical Glycosylation, Lipid II, Polyprenyls, Total synthesis, Peptidoglycan

Supporting Information

Format: DOCX Size: 7.4 MB   Download

How to Cite

When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Karak, M.; Cloonan, C. R.; Baker, B.; Cochrane, R. V. K.; Cochrane, S. A. Beilstein Arch. 2023, 202349. doi:10.3762/bxiv.2023.49.v1

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.