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Stabilization of the Acyclic Tautomer in Reducing Carbohydrates
Author(s) -
Mossine Valeri V.,
Barnes Charles L.,
Chance Deborah L.,
Mawhinney Thomas P.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200902123
Subject(s) - tautomer , chemistry , hydrogen bond , carbohydrate , fructose , stereochemistry , combinatorial chemistry , molecule , organic chemistry
Sweet structure : Acyclic reducing carbohydrate intermediates are typically impossible to crystallize. 1‐Amino‐1‐deoxy‐ D ‐fructose derivatives afford an exceptional example of the keto form in the crystalline state (see structure), possibly as a consequence of an interplay between the hydrophobic microenvironment around the carbonyl group and hydrogen‐bonding patterns.