New TRR-publication! Versatile synthesis of pathogen specific bacterial cell wall building blocks
Congratulations to Lukas Martin Wingen, Christina Braun, Marvin Rausch, Harald Gross, Tanja Schneider and Dirk Menche!
A modular three coupling strategy involving a versatile solid phase peptide synthesis enable access to pathogen specific lipid analogs in high yield, revealing high spectroscopic resolution of these key bacterial cell wall building blocks.
Full details on the design, strategies and tactics for development of a novel synthetic sequence to farnesyl lipid I and II analogs is reported. The modular route was based on a three coupling strategy involving an efficient solid phase synthesis of the elaborate peptide fragment, which proceeded with excellent yield and stereoselectivity and efficiently applied for convergent synthesis of 3-lipid I and II. Furthermore, the generality of this route was demonstrated by synthesis of 3-lipid I congeners that are characteristic for S. aureus and E. faecalis. All 3-lipid I and II building blocks were obtained in high purity revealing high spectroscopic resolution.
The full research paper can be accessed under: https://doi.org/10.1039/D2RA01915A