Sn-Beta zeolites with borate salts catalyse the epimerization of carbohydrates via an intramolecular carbon shift
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Gunther_2012-Sn-Beta zeolites.pdf
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Author(s)
Wang, Yuran
Ji, Yuewei
Michaelis, Vladimir K.
Gunther, William Robert
Hunt, Sean Thomas
Roman, Yuriy
Griffin, Robert Guy
Date Issued
October 2012
Journal
Nature Communications
Publisher
Nature Publishing Group
Citation
Gunther, William R., Yuran Wang, Yuewei Ji, Vladimir K. Michaelis, Sean T. Hunt, Robert G. Griffin, and Yuriy Roman-Leshkov. “Sn-Beta zeolites with borate salts catalyse the epimerization of carbohydrates via an intramolecular carbon shift.” Nature Communications 3 (October 9, 2012): 1109. © 2012 Nature Publishing Group, a division of Macmillan Publishers Limited
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Abstract
Carbohydrate epimerization is an essential technology for the widespread production of rare sugars. In contrast to other enzymes, most epimerases are only active on sugars substituted with phosphate or nucleotide groups, thus drastically restricting their use. Here we show that Sn-Beta zeolite in the presence of sodium tetraborate catalyses the selective epimerization of aldoses in aqueous media. Specifically, a 5 wt% aldose (for example, glucose, xylose or arabinose) solution with a 4:1 aldose:sodium tetraborate molar ratio reacted with catalytic amounts of Sn-Beta yields near-equilibrium epimerization product distributions. The reaction proceeds by way of a 1,2 carbon shift wherein the bond between C-2 and C-3 is cleaved and a new bond between C-1 and C-3 is formed, with C-1 moving to the C-2 position with an inverted configuration. This work provides a general method of performing carbohydrate epimerizations that surmounts the main disadvantages of current enzymatic and inorganic processes.
MIT Department
Massachusetts Institute of Technology. Department of Chemical Engineering
Massachusetts Institute of Technology. Department of Chemistry
Francis Bitter Magnet Laboratory (Massachusetts Institute of Technology)
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DOI of Published Version
https://doi.org/10.1038/ncomms2122
