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 alpha and beta anomers were studied. The observed variation in pyranose ring conformations in product compounds is explained in terms of C-2 substitution.
Suresh
Chiravakkattu G
CG
Division of Biochemical Sciences, National Chemical Laboratory, Pune 411 008, India. suresh@ems.ncl.res.in
Ravindran
Bindu
B
Pathak
Tanmaya
T
Rao
Krishnamurthy
K
Shashidharaprasad
J
J
Lokanath
N K
NK
D000606:Amino Sugars / Q000737:chemistry*; D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D003837:Deoxy Sugars / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D011714:Pyrans / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000606:Amino Sugars; D003837:Deoxy Sugars; D011714:Pyrans