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Structure-reactivity relationship of Amadori rearrangement products compared to related ketoses.

Martin Kaufmann, Philipp M Meissner, Daniel Pelke,Clemens Mügge,Lothar W Kroh

Carbohydrate Research（2016）

Cited 30|Views9
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Abstract
•Sugar degradation kinetics are related to isomerisation dynamics.•Amadori rearrangement products show complex isomerisation/mutarotation.•Isomerisation rates depend on C-1 substituent mediated intramolecular catalysis.•Fast 5C2 ↔ 2C5 ring inversion occurs in case of d-fructose-derived α-pyranoses.
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Key words
Isomerisation dynamics,Reactivity,Dynamic NMR spectroscopy,d-Fructose,Amadori compound,Ring inversion
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