Carbohydrate Research p. 1 - 26 (1981)
Update date:2022-09-26
Topics:
Duke, Colin C.
MacLeod, John K.
Williams, John F.
N.m.r. studies show that a concentrated (ca. 1.0 M ) aqueous solution of D-erythrose 4-phosphate is composed of an equilibrium mixture of the monomeric aldehyde and hydrated aldehyde forms, which interconvert rapidly, together with a major contribution from three dimeric forms.In dilute solutions (ca. 0.04 M ), the hydrated monomer is predominant and dimeric forms are not detectable at this concentration.The chemical structures and stereochemistry of the three dimers have been elucidated by (1)H- and (13)C n.m.r. spectroscopy of D-erythrose 4-phosphate and its (4,4-2H2) and (3,4,4'-2H3) derivatives, aided by the use of the model compounds, glycolaldehyde, D-glyceraldehyde, and DL-glyceraldehyde 3-phosphate, which also form dimers in concenrated aqueous solution.In some cases, the tert-butyldimethylsilyl derivatives of the model dimeric compounds were prepared and isolated.The two major dimers of D-erythrose 4-phosphate, I and II are asymmetrically substituted 1,3-dioxane and 1,3-dioxolane stuctures, respectively, and dimer III is the α anomer of dimer I.
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