Friday 5, October 2012; 3:00 p.m.; LSci 175

Dr. Andreas Franz
Associate Professor, Department of Chemistry,
University of the Pacific

Presents:

 “Carbohydrate Mimetics in Synthesis, NMR Structure Studies, and Chiral Differentiation”

The roles that oligosaccharides play in nature, their synthesis and metabolism are complex and remain poorly understood to this day. Detailed knowledge about carbohydrate structure and adequate structure elucidation methods are crucial for scientists to develop possible cures for carbohydrate-based diseases. The talk will discuss two classes of carbohydrate mimetics that we synthesized and whose structures were described by NMR, X-Ray spectroscopy, and molecular modeling. The rigidity of the one class of mimetics revealed a set of “standard” NMR coupling constants for 2,3-enopyranosyl rings in the unusual 5HO-conformation. Quantitative long-range HMBC-correlations revealed a sufficient number of experimental 3JH,C-values to match with those derived from molecular dynamics and statistical fitting to HCCC/HCOC Karplus-equations for satisfactory structure description. The talk will also discuss how such carbohdydrate mimetics could be used in future as chiral auxiliaries during stereodifferentiation reactions.