Stabilization of the Acyclic Tautomer in Reducing Carbohydrates

Stabilization of the Acyclic Tautomer in Reducing Carbohydrates

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 micr...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (30), p.5517-5520
Hauptverfasser: Mossine, Valeri V, Barnes, Charles L, Chance, Deborah L, Mawhinney, Thomas P
Format: Artikel
Sprache:eng
Schlagworte:
carbohydrates
Fructosamine - chemical synthesis
Fructosamine - chemistry
Hydrogen Bonding
Hydrophobic and Hydrophilic Interactions
hydrophobic effect
Isomerism
solid‐state structures
tautomerism
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Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200902123