Anomeric Effect. Origin and Consequences by Walter A. & Derek Horton (eds.) Szarek

By Walter A. & Derek Horton (eds.) Szarek

content material: The interplay among the ring-oxygen p-type lone pair and adjoining [sigma]-bonds in pyranose derivatives / Serge David --
The exo-anomeric influence / R.U. Lemieux, S. Koto, and D. Voisin --
Proton spin-lattice rest : a brand new, quantitative degree of aglycon-sugar interactions / J.M. Berry, L.D. corridor, D.G. Welder, and K.F. Wong --
The structural homes of the anomeric heart in pyranoses and pyranosides / G.A. Jeffrey --
points of conformational research of pentopyranosyl acetates, benzoates, and halides / Hans Paulsen, Peter Luger, and Fred R. Heiker --
The effect of reactant constitution and solvent on glycoside synthesis / Conrad Schuerch --
Conformational interactions in 1,4-heterobutane segments / Ernest L. Eliel and Eusebio Juaristi.

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As previously mentioned ( l j , many publications on the conformation of glycosidic linkages Have not taken into consideration the exo-anomeric effect and, therefore, the con­ clusions reached may require revision. Lemieux and coworkers (3) obtained evidence that hydration may have an influence on the anomeric and exo-anomeric effects. Painter (18) has studied the influence of cosolutes upon the con­ formations of carbohydrates in aqueous solution and concluded that the observations made are in general accord with influences on the anomeric and exo-anomeric effects.

Use t h e i n t e r p r o t o n n u c l e a r O v e r h a u s e r enhancement ex­ periment (14). The r e m a i n d e r o f t h i s d i s c u s s i o n w i l l be c o n c e r n e d w i t h f i r s t two o f t h e s e m e t h o d s . the T h e r e a r e a number o f ways o f u s i n g t h e r e g r e s s i o n a l a n a l y ­ s i s method and t h e s i m p l e s t , and f o r many p u r p o s e s t h e most p o w e r f u l o f t h e s e can be i l l u s t r a t e d w i t h r e s p e c t t o t h e d e t e r ­ mination of the r e l a x a t i o n c o n t r i b u t i o n s which the anomeric pro­ ton of thegalactopyranose residue of V r e c e i v e s from the protons o f t h e f r u c t o f u r a n o s e r i n g .

Ch003 Department of Chemistry, The University of British Columbia, Vancouver, British Columbia, Canada V6T 1W5 It is now well known that the anomeric effect of many substituents can dominate the conformations favoured by carbohydrate derivatives in solution. For example, all the pentopyransyl fluoride (2) and chloride derivatives (3) favour in solution that conformation in which the halogen substituent has an axial orientation - even in the case of the ß-D-xylopyranosyl derivatives where the C -chair conformation requires that all the substituents be axially oriented.

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