TY - JOUR
T1 - Diagnostic structural criteria for the anomeric effect in carbohydrates and inferences of general significance on their scope and limitations
AU - Schleifer, Leah
AU - Senderowitz, Hanoch
AU - Aped, Pinchas
AU - Tartakovsky, Evgeny
AU - Fuchs, Benzion
PY - 1990/9/30
Y1 - 1990/9/30
N2 - A systematic analysis of 529 carbohydrate structures that contain OCO units, retrieved from the Cambridge Structural Database, was performed with regard to the bond lengths (CO) and bond (COC and OCO) angles as they depend on the dihedral angles in the sequence COCOC. This dependence was then interpreted in terms of the anomeric effect. Known and new concepts that concern the manifestations of the anomeric and exo-anomeric effects were thus reassessed. A set of structural criteria of diagnostic value was defined which, together with qualifying arguments, allow evaluation of the scope and limitations of these stereoelectronic effects in carbohydrate systems.
AB - A systematic analysis of 529 carbohydrate structures that contain OCO units, retrieved from the Cambridge Structural Database, was performed with regard to the bond lengths (CO) and bond (COC and OCO) angles as they depend on the dihedral angles in the sequence COCOC. This dependence was then interpreted in terms of the anomeric effect. Known and new concepts that concern the manifestations of the anomeric and exo-anomeric effects were thus reassessed. A set of structural criteria of diagnostic value was defined which, together with qualifying arguments, allow evaluation of the scope and limitations of these stereoelectronic effects in carbohydrate systems.
UR - http://www.scopus.com/inward/record.url?scp=0040128277&partnerID=8YFLogxK
U2 - 10.1016/0008-6215(90)84003-D
DO - 10.1016/0008-6215(90)84003-D
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AN - SCOPUS:0040128277
SN - 0008-6215
VL - 206
SP - 21
EP - 39
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 1
ER -