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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.

Original publication

DOI

10.1039/P19810003186

Type

Journal article

Journal

Journal of the Chemical Society, Perkin Transactions 1

Publication Date

01/12/1981

Pages

3186 - 3195