Mechanism and Stereoselectivity of Zeolite-catalysed Sugar Isomerisation in Alcohols

Saravanamurugan Shunmugavel; Anders Riisager; Esben Taarning; Sebastian Meier

doi:10.1039/C6CC05592C

Mechanism and Stereoselectivity of Zeolite-catalysed Sugar Isomerisation in Alcohols

Saravanamurugan Shunmugavel
, Anders Riisager
, Esben Taarning
, Sebastian Meier

Department of Chemistry

Haldor Topsoe AS

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Glucose isomerisation to fructose can occur by different pathways and the mechanism of zeolite-catalysed glucose isomerisation in methanol has remained incompletely understood. Herein, the mechanism is studied using an 1H-13C HSQC NMR assay resolving different fructose isotopomers. We find that zeolite-catalysed glucose isomerisation proceeds predominantly via a hydride shift into the pro-R position of fructose, thus resembling the stereoselectivity of the enzymatic isomerisation process.

Original language	English
Journal	Chemical Communications
Volume	52
Pages (from-to)	12773-12776
Number of pages	4
ISSN	1359-7345
DOIs	https://doi.org/10.1039/C6CC05592C
Publication status	Published - 2016

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title = "Mechanism and Stereoselectivity of Zeolite-catalysed Sugar Isomerisation in Alcohols",

abstract = "Glucose isomerisation to fructose can occur by different pathways and the mechanism of zeolite-catalysed glucose isomerisation in methanol has remained incompletely understood. Herein, the mechanism is studied using an 1H-13C HSQC NMR assay resolving different fructose isotopomers. We find that zeolite-catalysed glucose isomerisation proceeds predominantly via a hydride shift into the pro-R position of fructose, thus resembling the stereoselectivity of the enzymatic isomerisation process.",

author = "Saravanamurugan Shunmugavel and Anders Riisager and Esben Taarning and Sebastian Meier",

year = "2016",

doi = "10.1039/C6CC05592C",

language = "English",

volume = "52",

pages = "12773--12776",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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T1 - Mechanism and Stereoselectivity of Zeolite-catalysed Sugar Isomerisation in Alcohols

AU - Shunmugavel, Saravanamurugan

AU - Riisager, Anders

AU - Taarning, Esben

AU - Meier, Sebastian

PY - 2016

Y1 - 2016

N2 - Glucose isomerisation to fructose can occur by different pathways and the mechanism of zeolite-catalysed glucose isomerisation in methanol has remained incompletely understood. Herein, the mechanism is studied using an 1H-13C HSQC NMR assay resolving different fructose isotopomers. We find that zeolite-catalysed glucose isomerisation proceeds predominantly via a hydride shift into the pro-R position of fructose, thus resembling the stereoselectivity of the enzymatic isomerisation process.

AB - Glucose isomerisation to fructose can occur by different pathways and the mechanism of zeolite-catalysed glucose isomerisation in methanol has remained incompletely understood. Herein, the mechanism is studied using an 1H-13C HSQC NMR assay resolving different fructose isotopomers. We find that zeolite-catalysed glucose isomerisation proceeds predominantly via a hydride shift into the pro-R position of fructose, thus resembling the stereoselectivity of the enzymatic isomerisation process.

U2 - 10.1039/C6CC05592C

DO - 10.1039/C6CC05592C

M3 - Journal article

SN - 1359-7345

VL - 52

SP - 12773

EP - 12776

JO - Chemical Communications

JF - Chemical Communications

ER -

Mechanism and Stereoselectivity of Zeolite-catalysed Sugar Isomerisation in Alcohols

Abstract

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