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Versatile synthesis of pathogen specific bacterial cell wall building blocks†
Lukas Martin Wingen,Christina Braun,Harald Gross,Tanja Schneider,Dirk Menche
RSC Advances Pub Date : 05/18/2022 00:00:00 , DOI:10.1039/D2RA01915A
Abstract

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 was efficiently applied for the 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.

Graphical abstract: Versatile synthesis of pathogen specific bacterial cell wall building blocks
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