| Sn-Beta zeolites with borate salts catalyse the epimerization of carbohydrates via an intramolecular carbon shift. | |
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MedLine Citation:
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PMID: 23047667 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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William R Gunther; Yuran Wang; Yuewei Ji; Vladimir K Michaelis; Sean T Hunt; Robert G Griffin; Yuriy Román-Leshkov |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: Nature communications Volume: 3 ISSN: 2041-1723 ISO Abbreviation: Nat Commun Publication Date: 2012 |
Date Detail:
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Created Date: 2012-10-10 Completed Date: 2013-02-01 Revised Date: 2013-03-21 |
Medline Journal Info:
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Nlm Unique ID: 101528555 Medline TA: Nat Commun Country: England |
Other Details:
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Languages: eng Pagination: 1109 Citation Subset: IM |
Affiliation:
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Department of Chemical Engineering, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Arabinose
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chemistry Borates / chemistry* Carbohydrates / chemistry* Catalysis Glucose / chemistry Molecular Structure Xylose / chemistry Zeolites / chemistry* |
| Grant Support | |
ID/Acronym/Agency:
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EB-001960/EB/NIBIB NIH HHS; EB-002026/EB/NIBIB NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Borates; 0/Carbohydrates; 0/Xylose; 1318-02-1/Zeolites; 1330-43-4/sodium borate; 147-81-9/Arabinose; 50-99-7/Glucose |
| Comments/Corrections | |
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