STUDIES ON THE REACTIVITY OF BISGLYCOALDEHYDE PHOSPHODIESTER IN ALKALINE-SOLUTION

The behaviour of bisglycoaldehyde phosphodiester in alkaline solution has previously been investigated by reducing, dephosphorylating and ac etylating the products. The detection of threitol and erythreitol tetr aacetates by GC coupled with kinetic arguments suggested that bisglyco aldehyde phosphodiester undergoes rapid intramolecular aldolisation to give a mixture of erythrose and threose-2,4-cyclophosphates (Pitsch, S.; Pombo-Villar, E.; Eschenmoser, A. Helv. Chim. Acta 1994, 77, 2251) . In this paper, electrospray mass spectroscopy, deuteration studies a nd comparison with synthetic materials are used to confirm and augment these earlier findings. Copyright (C) 1996 Elsevier Science Ltd