Enantioselective Keto–Enol Tautomerism of 3-Hydroxyflavones Upon Molecular Complex Formation of Their α-Diketo Forms with Carbohydrates in Aqueous Solutions

Enantioselective Keto–Enol Tautomerism of 3-Hydroxyflavones Upon Molecular Complex Formation of Their α-Diketo Forms with Carbohydrates in Aqueous Solutions

Complementary physicochemical methods (UV, IR, ORD) found that the α-diketo tautomer of 3-hydroxyflavones formed complexes with carbohydrates in water. The contribution of the flavone α-diketone increased sharply because it was stabilized after reacting with a carbohydrate cis-diol. The newly formed...

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Bibliographic Details
Published in:Chemistry of natural compounds Vol. 52; no. 4; pp. 579 - 584
Main Authors: Pogodaeva, N. N., Sukhov, B. G., Medvedeva, S. A.
Format: Journal Article
Language:English
Published: New York Springer US 01-07-2016
Springer
Subjects:
Enantiomers
Enols
Galactose
Isoflavones
Medicine
Organic Chemistry
Pharmacy
Plant Sciences
Polysaccharides
carbohydrates
3-hydroxyflavones
Cotton effect
arabinogalactan
molecular complexes
optical rotary dispersion
UV and IR spectroscopy
keto–enol tautomerism
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Summary:Complementary physicochemical methods (UV, IR, ORD) found that the α-diketo tautomer of 3-hydroxyflavones formed complexes with carbohydrates in water. The contribution of the flavone α-diketone increased sharply because it was stabilized after reacting with a carbohydrate cis-diol. The newly formed chiral center of the tautomeric diketo flavones was induced asymmetrically. The complexing ability of the carbohydrates was inversely proportional to their degree of hydration (and decreased in the order maltoseglucose-galactose-arabinose).
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-016-1717-1