172987-06-3Relevant academic research and scientific papers
Carbopeptoids: Peptides and diketopiperazines incorporating the anomeric centre of mannopyranose
Long, Daniel D.,Tennant-Eyles, Richard J.,Estevez, Juan C.,Wormald, Mark R.,Dwek, Raymond A.,Smith, Martin D.,Fleet, George W.J.
, p. 807 - 813 (2007/10/03)
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.
Spirodiketopiperazines at the anomeric position of mannopyranose: Novel N-linked glycopeptides incorporating an α-amino acid at the anomeric position of mannopyranose
Estevez, Juan C.,Long, Daniel D.,Wormald, Mark R.,Dwek, Raymond A.,Fleet, George W. J.
, p. 8287 - 8290 (2007/10/02)
The first synthesis of a spirodiketopiperazine at the anomeric carbon of a pyranose sugar is described; an N-acylated bicyclic amino [2.2.2.] lactone provides access to a new class of glycopeptide analogues of pyranoses and determines the anomeric configuration of the spirodiketopiperazine. The mannopyranose may be equilibrated to the more stable furanose form.
