Synthesis and characterisation of N-glycosyl amines from the reaction between 4,6-O-benzylidene-D-glucopyranose and substituted aromatic amines and also between 2-(o-aminophenyl)benzimidazole and pentoses or hexoses

Mohan Das, T. ; Rao, Chebrolu P. ; Kolehmainen, Erkki (2001) Synthesis and characterisation of N-glycosyl amines from the reaction between 4,6-O-benzylidene-D-glucopyranose and substituted aromatic amines and also between 2-(o-aminophenyl)benzimidazole and pentoses or hexoses Carbohydrate Research, 334 (4). pp. 261-269. ISSN 0008-6215

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/S0008-6215(01)00202-6

Abstract

Twelve N-glycosyl amines were synthesised using 4,6-O-benzylidene-D-glucopyranose and different substituted aromatic amines, including some diamines that resulted in bis-glycosyl amines. Another set of six N-glycosyl amines was synthesised using different hexoses and pentoses and 2-(o-aminophenyl)benzimidazole. All compounds were isolated as solid products and purified, their elemental compositions were established, and these were characterised by NMR (1H and 13C), UV-Vis, and FTIR spectroscopy, by FAB mass spectrometry (molecular-ion peaks gave molecular weights), and by their optical rotations. While the protected saccharide, 4,6-O-benzylidene-D-glucopyranose, exists as a mixture of β and α anomers in solution, the corresponding N-glycosyl amines were of only the β anomeric form as determined by NMR and FTIR spectroscopy. On the other hand, N-glycosyl amines synthesised from 2-(o-aminophenyl)benzimidazole prefer the α anomeric form, and in two cases a mixture of both the β and the α anomers were observed. The trends observed in the chemical shifts were compared among different products.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:N-Glycosyl Amines; α and β Anomers; Optical rotation; 4,6-O-Benzylidene-D-glucopyranose; 4,6-O-Butylidene-D-glucopyranose; 2-(o-Aminophenyl)benzimidazole; Hydrogen-bonding Interaction
ID Code:79130
Deposited On:24 Jan 2012 12:12
Last Modified:19 Apr 2012 05:46

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