Abstract
The syntheses of peptidoglycan (PG)-derived peptides containing meso-diaminopimelic acid (meso-Dap) are typically quite lengthy due to the need to prepare orthogonally protected meso-Dap. In this work, the preparation of the PG pentapeptide containing the isosteric analog meso-oxa-Dap is described. The synthesis relies on the ring opening of a peptide embedded aziridine via the attack of a serine residue. The pentapeptide was attached to a GlcNAc-anhydro-MurNAc disaccharide, to produce a putative substrate for the AmpG pore protein.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Acetylglucosamine / chemistry*
-
Diaminopimelic Acid / analogs & derivatives*
-
Diaminopimelic Acid / chemical synthesis
-
Diaminopimelic Acid / chemistry
-
Disaccharides / chemistry*
-
Muramic Acids / chemistry*
-
Oligopeptides / chemical synthesis*
-
Oligopeptides / chemistry
-
Oxazoles / chemical synthesis
-
Oxazoles / chemistry
-
Peptidoglycan / chemistry*
Substances
-
Disaccharides
-
Muramic Acids
-
Oligopeptides
-
Oxazoles
-
Peptidoglycan
-
N-acetylmuramic acid
-
Diaminopimelic Acid
-
Acetylglucosamine