1962
DOI: 10.1126/science.135.3501.367
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Taste-Structure Correlation with α-D-Mannose and β-D-Mannose

Abstract: The so-called ambiguity of taste perception of D-mannose has been traced to actual differences in taste between the two anomers of this substance. Preliminary data indicate strongly that the alpha-anomer is sweet (sucrose-like) and the beta-anomer is bitter (quinine-like). The difference in taste is attributed to the slight difference in structures of the anomers.

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Cited by 33 publications
(13 citation statements)
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“…D-Mannose is the 2-epimer of glucose and exists primarily as sweet-tasting α- (67%) or as a bitter-tasting β- (33%) anomer of the pyranose [6,7]; furanose forms comprise <2%. Mannose is ~5x as active as glucose in non-enzyamtic glycation [8], which may explain why evolution did not favor it as a biological energy source.…”
Section: Mannose Chemistrymentioning
confidence: 99%
“…D-Mannose is the 2-epimer of glucose and exists primarily as sweet-tasting α- (67%) or as a bitter-tasting β- (33%) anomer of the pyranose [6,7]; furanose forms comprise <2%. Mannose is ~5x as active as glucose in non-enzyamtic glycation [8], which may explain why evolution did not favor it as a biological energy source.…”
Section: Mannose Chemistrymentioning
confidence: 99%
“…Reducing sugars typically exist as a mixture of α and β anomers, as natural interconversion between open‐ and closed‐chain forms results in anomerization to an equilibrium mixture of α and β anomers within a few hours of solvation. Differences in sweetness have been found between the α‐ and β‐anomeric forms of several sugars, though only for lactose has the magnitude of that difference been explicitly quantified (Pangborn and Gee ; Steinhardt and others ; Parrish and others ; Sakaguchi and others ). Pangborn and Gee () found the α‐form of fructose, glucose, and galactose to be the sweeter anomer, whereas the β‐form of lactose was judged to be sweeter than α‐lactose (Parrish and others ).…”
Section: Technical and Functional Roles Of Sugars In Foods And Beveragesmentioning
confidence: 99%
“…It is important to note, that although α‐ and β‐sugar anomers may differ in their degree of sweetness, d ‐ and l ‐isomers have the same degree of sweetness. For instance, α‐d‐mannose is found to be sweet in taste, although its anomer β‐d‐mannose is bitter and not sweet (Steinhardt and others ).…”
Section: Technical and Functional Roles Of Sugars In Foods And Beveragesmentioning
confidence: 99%
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“…Similarly, there is a difference in taste between D-and L-mannose. In fact, the two anomers of D-mannose possess different tastes (50). α-D-mannose is sweet like sucrose, whereas β-D-mannose is bitter like quinine (Table VI).…”
Section: Properties Of Taste Moleculesmentioning
confidence: 98%