title: Synthesis of the NAG-NAM disaccharide via a versatile intermediate.
abstract: A simple strategy for the synthesis of a β-GlcNAc-(1→4)-MurNAc (NAG-NAM) moiety, crucial for the preparation of synthetic components of a bacterial peptidoglycan, was achieved. This strategy relies on the use of three O-protecting groups, 4,6-O-benzilidene acetal, benzyl, and acetyl group, which allows further regioselective manipulation at O-3, O-4 positions, and on the insertion of the peptide chain at the lactate moiety in an advanced and versatile intermediate. Overall, a simple route to achieve the biological relevant NAG-NAM is presented, which may serve as a conceptual framework in the designing of synthetic strategies of different natural and non-natural polysaccharides.
authors.affiliation: REQUIMTE-CQFB, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal.
authors.forename: Ramu
authors.initials: R
authors.lastname: Enugala
authors.affiliation: REQUIMTE-CQFB, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal.
authors.forename: Marina J D
authors.initials: MJ
authors.lastname: Pires
authors.affiliation: REQUIMTE-CQFB, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal. Electronic address: mmbmarques@fct.unl.pt.
authors.forename: M Manuel B
authors.initials: MM
authors.lastname: Marques
mesh_terms: D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D004187:Disaccharides
keywords: Glycosylation; N-Acetyl glucosamine; NAG–NAM; Peptidoglycan; Protecting group