Abstract
Peptidoglycans, the ubiquitous constituents of bacterial cell walls, exhibit versatile biological activities including immunomodulating properties. We have synthesized novel derivatives of peptidoglycan monomer (PGM) 1 (R1-L-Ala-D-iGln-m-Dap(R2)-D-Ala-D-Ala, R1 = GlcNAc-MurNAc, R2 = H) with attached adamant-2-yl (Ad) residues: Ad-CH2CO-PGM 2 (Ad-PGM, R1 = GlcNAc-MurNAc, R2 = Ad) and the corresponding Ad-CH2CO-pentapeptide 3 (Ad-PP, R1 = H, R2 = Ad). Attachement of a bulky adamantyl group may, in principle, introduce conformational restraints into the PGM molecule and the pentapeptide derived thereof. We have therefore investigated the conformational properties of 2 and 3, using 2D NMR spectroscopy and molecular modelling, for solutions in DMSO.
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