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2020•Organic LettersRequires access

Synthesis of a meso-Oxa-Diaminopimelic Acid Containing Peptidoglycan Pentapeptide and Coupling to the GlcNAc-anhydro-MurNAc Disaccharide

Arvind S. Soni, Condarache M. Vacariu, Jeff Y. Chen, Martin E. Tanner

Open publisher page 8 citations

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.

About this research paper

What this paper is about

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.

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OpenAlex reports 8 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available 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.

Key concepts: Pentapeptide repeat, Peptidoglycan, Diaminopimelic acid, Chemistry, Disaccharide, Stereochemistry, Serine, Residue (chemistry)

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Synthesis of a meso-Oxa-Diaminopimelic Acid Containing Peptidoglycan Pentapeptide and Coupling to the GlcNAc-anhydro-MurNAc Disaccharide — Research Paper | ScholarLens