Source:http://linkedlifedata.com/resource/pubmed/id/11527527
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
4
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pubmed:dateCreated |
2001-8-30
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pubmed:abstractText |
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 beta and alpha anomers in solution, the corresponding N-glycosyl amines were of only the beta anomeric form as determined by NMR and FTIR spectroscopy. On the other hand, N-glycosyl amines synthesised from 2-(o-aminophenyl)benzimidazole prefer the alpha anomeric form, and in two cases a mixture of both the beta and the alpha anomers were observed. The trends observed in the chemical shifts were compared among different products.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/2-(2'-aminophenyl)benzimidazole,
http://linkedlifedata.com/resource/pubmed/chemical/4,6-O-benzylidene-D-glucopyranose,
http://linkedlifedata.com/resource/pubmed/chemical/Amines,
http://linkedlifedata.com/resource/pubmed/chemical/Benzimidazoles,
http://linkedlifedata.com/resource/pubmed/chemical/Glucose,
http://linkedlifedata.com/resource/pubmed/chemical/Hexoses,
http://linkedlifedata.com/resource/pubmed/chemical/Pentoses,
http://linkedlifedata.com/resource/pubmed/chemical/Polycyclic Hydrocarbons, Aromatic
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pubmed:status |
MEDLINE
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pubmed:month |
Sep
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pubmed:issn |
0008-6215
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
7
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pubmed:volume |
334
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
261-9
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:11527527-Amines,
pubmed-meshheading:11527527-Benzimidazoles,
pubmed-meshheading:11527527-Carbohydrate Sequence,
pubmed-meshheading:11527527-Glucose,
pubmed-meshheading:11527527-Glycosylation,
pubmed-meshheading:11527527-Hexoses,
pubmed-meshheading:11527527-Hydrogen Bonding,
pubmed-meshheading:11527527-Molecular Sequence Data,
pubmed-meshheading:11527527-Nuclear Magnetic Resonance, Biomolecular,
pubmed-meshheading:11527527-Pentoses,
pubmed-meshheading:11527527-Polycyclic Hydrocarbons, Aromatic
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pubmed:year |
2001
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pubmed:articleTitle |
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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pubmed:affiliation |
Bioinorganic Laboratory, Department of Chemistry, Indian Institute of Technology Bombay, Powai, 400 076, Mumbai, India.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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