Document Detail

A method for obtaining equilibrium tautomeric mixtures of reducing sugars via glycosylamines using nonaqueous media.
MedLine Citation:
PMID:  12007481     Owner:  NLM     Status:  MEDLINE    
Equilibrium tautomeric mixtures of several mono- and disaccharides are obtained in anhydrous form, without the use of water, by reacting the commercially available reducing sugars with ammonia gas in dry methanol, followed by the concentration of the resultant solution to dryness. Mutarotation and hydrolysis of the initially formed glycosylamine in the resultant medium account for the transformation. Equilibrium anomeric mixtures enriched in the beta-form of commercially available sugars such as alpha-D-glucose and alpha-lactose have not only vastly increased solubility, but are also synthetically valuable as these can be readily converted to the methyl/benzyl/trimethylsilyl ether and other derivatives for further transformations.
Sikkander Sulthan Allavudeen; Balagurunathan Kuberan; Duraikkannu Loganathan
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Carbohydrate research     Volume:  337     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  2002 May 
Date Detail:
Created Date:  2002-05-14     Completed Date:  2002-12-03     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  965-8     Citation Subset:  IM    
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India.
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MeSH Terms
Amines / chemistry
Disaccharides / chemical synthesis*,  chemistry*
Ethanol / chemistry
Glucose / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Monosaccharides / chemical synthesis*,  chemistry*
Reg. No./Substance:
0/Amines; 0/Disaccharides; 0/Monosaccharides; 50-99-7/Glucose; 64-17-5/Ethanol

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