Deoxo-trifluoro analog of d-glucose

ORGN 681

Stefano Bresciani Sr., and David O'Hagan, School of Chemistry (Centre for Biomolecular Sciences), University of St Andrews, North Haugh, St Andrews, Fife, Uk, ky169ST, St Andrews, United Kingdom
A preparation of the 2,3,4 tri-deoxo-fluoro analogue of D-glucose is under investigation. A synthesis is addressed to provide moieties bearing three vicinal fluorines placed in a stereoselective manner. Replacement of F for OH removes the hydrogen bonding donor ability of the OH substituent, however the polarity of the C-F bond mimics that of the C-O bond [1]. Such inherent polarity is an important factor in determining carbohydrate conformation. The 2,3,4 tri-deoxo-trifluoro analogue of glucose represents an exciting sugar mimetic which will allow examination of the influence of polarity but without the hydrogen bonding donor/acceptor ability of the OH groups in carbohydrate interactions. Such compounds will be explored in suitable enzymatic reactions and protein binding studies.