Stabilization of the Acyclic Tautomer in Reducing Carbohydrates

Abstract

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.