Optimizations of lipid II synthesis: an essential glycolipid precursor in bacterial cell wall synthesis and a validated antibiotic target

Milandip Karak, Cian R. Cloonan, Brad Baker, Rachel V. K. Cochrane, Stephen A. Cochrane*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Downloads (Pure)

Abstract

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.
Original languageEnglish
Pages (from-to)220–227
JournalBeilstein Journal of Organic Chemistry
Volume20
DOIs
Publication statusPublished - 06 Feb 2024

Keywords

  • Chemical Glycosylation, Lipid II, Polyprenyls, Total synthesis, Peptidoglycan

Fingerprint

Dive into the research topics of 'Optimizations of lipid II synthesis: an essential glycolipid precursor in bacterial cell wall synthesis and a validated antibiotic target'. Together they form a unique fingerprint.

Cite this