Structure of glycosylamines and diglycosylamines in the arabinose, mannose, and rhamnose series

✍ Scribed by Kazimir Linek; Juraj Alföldi; Jacques Defaye

• Book ID: 102992897
• Publisher: Elsevier Science
• Year: 1993
• Tongue: English
• Weight: 436 KB
• Volume: 247
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(93)84267-a

✦ Synopsis

Aldoses react with ammonia, generally to give cyclic products (glycosylamines), which may further undergo spontaneous transglycosylation to yield diglycosylamines. The reaction has been known since the pioneering work of Isbell and Frush', who assigned the anomeric configuration of a number of glycosylamines on the basis of their optical rotations. The structures of the corresponding diglycosylamines is, however, still uncertain. Furthermore, in some instances, anomerization reactions have been shown to occur upon 0-acetylation'. In a previous paper', the structure of glycosylamines and diglycosylamines derived from o-glucose and o-xylose have been firmly assigned using 'H and 13C NMR spectroscopy. The results are now extended in the arabinose, mannose, and rhamnose series.

cY-L-Arabinopyranosylamine was earlier prepared by Isbell and Frush3, and its anomeric configuration assigned2 on the basis of Hudson's isorotation rules. a-D-~abinopyranosylamine * Corresponding author.