Deoxo-trifluoro analog of d-glucose

ORGN 681

Stefano Bresciani Sr., sb559@st-andrews.ac.uk and David O'Hagan, do1@st-andrews.ac.uk. 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.