Structural studies on C-2 substitution in a new set of synthetic aminodideoxy sugars: the steric bulk at C-2 influences the puckering of the pyranose ring

Synthesis and single-crystal X-ray structural analyses of selected aminodideoxy sugars with different group substitutions at the C-2 position were carried out. Product formation and X-ray crystallographic determination of the products from C-2 substitution in both α and β anomers were studied. The o...

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Bibliographic Details
Published in:Carbohydrate research 2002-09, Vol.337 (16), p.1507-1512
Main Authors: Suresh, Chiravakkattu G., Ravindran, Bindu, Pathak, Tanmaya, Rao, Krishnamurthy Narasimha, Shashidharaprasad, J., Lokanath, N.K.
Format: Article
Language:English
Subjects:
Amino sugars
Amino Sugars - chemistry
C-2 Substitution
Carbohydrate Conformation
Crystallography, X-Ray
Deoxy Sugars - chemistry
Magnetic Resonance Spectroscopy
Models, Molecular
Pyranose conformation
Pyrans - chemistry
Stereoisomerism
Steric hindrance
Structure-Activity Relationship
α and β Anomers
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Summary:Synthesis and single-crystal X-ray structural analyses of selected aminodideoxy sugars with different group substitutions at the C-2 position were carried out. Product formation and X-ray crystallographic determination of the products from C-2 substitution in both α and β anomers were studied. The observed variation in pyranose ring conformations in product compounds is explained in terms of C-2 substitution. Graphic
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(02)00208-2