2006
DOI: 10.1016/j.carres.2006.02.035
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A theoretical study of glucose mutarotation in aqueous solution

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Cited by 75 publications
(73 citation statements)
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“…Lefort et al produced predominantly amorphous α-lactose by controlled ball milling of anhydrous α-lactose for 30 h. Upon storage of these samples at elevated temperatures approaching the glass transition of lactose, a solid state mutarotation to the β anomer was observed (23). A final ratio of 50% β and 50% α indicated that the mechanism in the solid state is different from the mutarotation reaction pathway recorded in aqueous solution (23), where at equilibrium a typical ratio of 63% β and 37% α has been recorded (8,11). A 1:1 ratio of anomers is almost never observed for spray or freeze dried amorphous lactose and furthermore there is a broad range of anomeric ratios reported (18,19,24,25).…”
Section: Introductionmentioning
confidence: 96%
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“…Lefort et al produced predominantly amorphous α-lactose by controlled ball milling of anhydrous α-lactose for 30 h. Upon storage of these samples at elevated temperatures approaching the glass transition of lactose, a solid state mutarotation to the β anomer was observed (23). A final ratio of 50% β and 50% α indicated that the mechanism in the solid state is different from the mutarotation reaction pathway recorded in aqueous solution (23), where at equilibrium a typical ratio of 63% β and 37% α has been recorded (8,11). A 1:1 ratio of anomers is almost never observed for spray or freeze dried amorphous lactose and furthermore there is a broad range of anomeric ratios reported (18,19,24,25).…”
Section: Introductionmentioning
confidence: 96%
“…This mechanism is based on the literature reports of the mutarotation for related sugars principally glucose (11,12). It is currently believed that the mutarotation of lactose involves the formation of the free aldehyde form of the glucose unit which is initiated by the protonation of the O5, followed by breakage of the O1-H bond (11,12). The starting state in the reaction scheme is the α form, (Fig.…”
Section: Introductionmentioning
confidence: 98%
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“…Mutarotation has been the subject of intense experimental studies in the previous century [5,6], but it has been studied only in solution. Recently, QM calculations were performed by Da Silva et al to understand the mechanism responsible for this phenomenon [7]. The authors performed calculations of energy barriers for intra as well as intermolecular mechanisms of mutarotation of glucose.…”
Section: Introductionmentioning
confidence: 99%
“…It is known that for some reactions in condensed phase, like the glucose mutarotation in aqueous solution, 30 the solvent-assisted pathway is much more favored than the intramolecular pathway. Taking into account this possibility, and once the ammonium salt can act as another proton donator besides the chiral alcohol, the following steps were investigated.…”
Section: The Intermolecular Mechanism (B)mentioning
confidence: 99%