Structural effects of oxidation on sugars: glucose as a precursor of gluconolactone and glucuronolactone

Although structural information on sugars is wide, experimental studies on the oxidation products of sugars in the gas phase, free from solvent interactions, have been rarely reported. We present an experimental work on the changes in the structure and interactions of two products of glucose oxidati...

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Published inChemical communications (Cambridge, England) Vol. 6; no. 4; pp. 532 - 535
Main Authors Parra-Santamaria, Maider, Insausti, Aran, Alonso, Elena R, Basterretxea, Francisco J, Cocinero, Emilio J
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 14.05.2024
Subjects
Gluconates - chemistry
Gluconolactone
Glucose
Glucose - chemistry
Lactones - chemistry
Molecular Structure
Oxidation
Oxidation-Reduction
Precursors
Sugar
Vapor phases
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Summary:Although structural information on sugars is wide, experimental studies on the oxidation products of sugars in the gas phase, free from solvent interactions, have been rarely reported. We present an experimental work on the changes in the structure and interactions of two products of glucose oxidation ( d -glucono-1,5-lactone ( GlcL ) and d -glucurono-6,3-lactone ( GlcurL )) with respect to their precursor. Features such as intramolecular interactions, ring puckering and tautomerism were observed. This atomic-resolution study reveals glucose changes due to oxidation, exploring key carbohydrate aspects like hydrogen bonding, ring-puckering, anomeric effect, and tautomeric selection. Results confirm mutarotation suppression in the gas phase.
Bibliography:https://doi.org/10.1039/d4cc00735b
Electronic supplementary information (ESI) available. See DOI
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d4cc00735b