Title: Alternative Sweeteners

372 White and Osberger
Figure 1 Cyclic tautomers of fructose. (From Ref. 7.)
NMR measurements at different temperatures demonstrate that the change in
relative sweetness is directly related to the shift in tautomeric equilibrium as
temperature is increased, as illustrated in Table 4 (9). On the basis of the correlation
between fructose sweetness and mutarotational behavior, Shallenberger deduced
that the furanoses are nearly devoid of sweet taste (6). Although this deduction
is based primarily on conformational considerations, it is evident that an
increase in the furanose anomer at the expense of the pyranose form will cause
a reduction in perceived sweetness.