Sn-Beta zeolites with borate salts catalyse the epimerization of carbohydrates via an intramolecular carbon shift

William R. Gunther, Yuran Wang, Yuewei Ji, Vladimir K. Michaelis, Sean T. Hunt, Robert G. Griffin and Yuriy Román-Leshkov ()
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William R. Gunther: Massachusetts Institute of Technology
Yuran Wang: Massachusetts Institute of Technology
Yuewei Ji: Massachusetts Institute of Technology
Vladimir K. Michaelis: Massachusetts Institute of Technology
Sean T. Hunt: Massachusetts Institute of Technology
Robert G. Griffin: Massachusetts Institute of Technology
Yuriy Román-Leshkov: Massachusetts Institute of Technology

Nature Communications, 2012, vol. 3, issue 1, 1-8

Abstract: 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.

Date: 2012
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DOI: 10.1038/ncomms2122

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