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The Stereochemical Basis of Bitterness in Sugar Analogues
Author(s) -
Lee C. K.
Publication year - 1977
Publication title -
starch ‐ stärke
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.62
H-Index - 82
eISSN - 1521-379X
pISSN - 0038-9056
DOI - 10.1002/star.19770290606
Subject(s) - sweetness , chemistry , anomer , sugar , hydrogen bond , molecule , stereochemistry , glycoside , oxygen atom , taste , ring (chemistry) , organic chemistry , biochemistry
Bitterness of sugars and their derivatives appears to be the result of polar as well as hydrophobic molecular features. It is multifunctional and the ring oxygen atom, the anomeric oxygen atom and the C‐2 hydroxyl group (and possibly the C‐6 hydroxyl group), all of which constitute the most polar and highly reactive “end” of the sugar molecule, together interact to elicit bitterness. The configuration of the substituents on C‐1 and possibly on C‐2 is critical in determining bitterness in many sugars an indeed β‐glycosides and β‐linked disaccharides are more likely to be bitter than α‐linked anomers. Unlike sweetness, no distinct interorbital distances can yet be established for bitterness. However, current hydrogen bond theories of sweetness seem suffice to explain bitterness in most types of sugar analogue. “Polarisation” of bitter/sweet molecules on taste receptors are also discussed and evidence obtained suggests that at least some of the sweet and bitter receptor sites might be extremely close to one another, and probably within 3–4 Å.