Analysis of the chirality of [16O,17O,18O] phosphate esters by 31P nuclear magnetic resonance spectroscopy

Abstract

A stereospecific method for cyclising D-glucose 6-[¹⁶O,¹⁷O,¹⁸O]phosphate and adenosine 5′-[¹⁶O,¹⁷O,¹⁸O]-phosphate to their conformationally locked six-membered cyclic phosphate diesters has been developed. Using [¹⁶O,¹⁷O,¹⁸O]phosphate esters of known absolute configuration it is shown by ³¹P n.m.r. spectroscopy, after esterification to the axial and equatorial triesters, that the cyclisation occurs with inversion of configuration. It is now possible, therefore, to determine the chirality at phosphorus of D-glucose 6-[¹⁶O,¹⁷O,¹⁸O]phosphate and adenosine 5′-[¹⁶O,¹⁷O,¹⁸O]phosphate by this procedure.