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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

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Title 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
 
Creator MOHAN DAS, T
RAO, CHEBROLU P
KOLEHMAINEN, ERKKI
 
Subject synthesis (chemical)
optical rotation
molecular weight
mass spectrometry
nuclear magnetic resonance spectroscopy
 
Description 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.
 
Publisher Elsevier
 
Date 2009-03-02T09:30:06Z
2011-11-25T18:20:37Z
2011-12-26T13:06:31Z
2011-12-27T05:54:21Z
2009-03-02T09:30:06Z
2011-11-25T18:20:37Z
2011-12-26T13:06:31Z
2011-12-27T05:54:21Z
2001
 
Type Article
 
Identifier Carbohydrate Research 334(4), 261-269
0008-6215
http://dx.doi.org/10.1016/S0008-6215(01)00202-6
http://hdl.handle.net/10054/839
http://dspace.library.iitb.ac.in/xmlui/handle/10054/839
 
Language en