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.
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Journal of the Chemical Society, Perkin Transactions 1
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