Carbopeptoids: peptides and diketopiperazines incorporating the anomeric centre of mannopyranose

An approach to the synthesis of D-mannopyranose derivatives incorporating an anomeric α-amino acid component is described. An N-acylated bicyclic [2.2.2] lactone, formed via an oxidative ring closure, provides access to a new class of glycopeptide analogues of D-mannopyranose and determines the anom...

Full description

Bibliographic Details
Main Authors: Long, D, Tennant-Eyles, R, Estevez, J, Wormald, M, Dwek, R, Smith, M, Fleet, G
Format: Journal article
Language:English
Published: 2001
Description
Summary:An approach to the synthesis of D-mannopyranose derivatives incorporating an anomeric α-amino acid component is described. An N-acylated bicyclic [2.2.2] lactone, formed via an oxidative ring closure, provides access to a new class of glycopeptide analogues of D-mannopyranose and determines the anomeric configuration of compounds derived therefrom. The mannopyranose diketopiperazine may be equilibrated to the more stable furanose form under basic conditions; in general, mannopyranose derivatives containing an α-amino acid moiety at the anomeric position are less stable than the mannofuranose isomers.