Carbopeptoids: peptides and diketopiperazines incorporating the anomeric centre of mannopyranose

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...

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التفاصيل البيبلوغرافية
المؤلفون الرئيسيون: Long, D, Tennant-Eyles, R, Estevez, J, Wormald, M, Dwek, R, Smith, M, Fleet, G
التنسيق: Journal article
اللغة:English
منشور في: 2001
الوصف
الملخص: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.

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