Literature DB >> 22665778

Metalloenzyme-like catalyzed isomerizations of sugars by Lewis acid zeolites.

Ricardo Bermejo-Deval1, Rajeev S Assary, Eranda Nikolla, Manuel Moliner, Yuriy Román-Leshkov, Son-Jong Hwang, Arna Palsdottir, Dorothy Silverman, Raul F Lobo, Larry A Curtiss, Mark E Davis.   

Abstract

Isomerization of sugars is used in a variety of industrially relevant processes and in glycolysis. Here, we show that hydrophobic zeolite beta with framework tin or titanium Lewis acid centers isomerizes sugars, e.g., glucose, via reaction pathways that are analogous to those of metalloenzymes. Specifically, experimental and theoretical investigations reveal that glucose partitions into the zeolite in the pyranose form, ring opens to the acyclic form in the presence of the Lewis acid center, isomerizes into the acyclic form of fructose, and finally ring closes to yield the furanose product. The zeolite catalysts provide processing advantages over metalloenzymes such as an ability to work at higher temperatures and in acidic conditions that allow for the isomerization reaction to be coupled with other important conversions.

Entities:  

Year:  2012        PMID: 22665778      PMCID: PMC3382492          DOI: 10.1073/pnas.1206708109

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  13 in total

1.  Synthetic glycolysis.

Authors:  Raul F Lobo
Journal:  ChemSusChem       Date:  2010-11-22       Impact factor: 8.928

2.  Mechanism of glucose isomerization using a solid Lewis acid catalyst in water.

Authors:  Yuriy Román-Leshkov; Manuel Moliner; Jay A Labinger; Mark E Davis
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

3.  Conversion of sugars to lactic acid derivatives using heterogeneous zeotype catalysts.

Authors:  Martin Spangsberg Holm; Shunmugavel Saravanamurugan; Esben Taarning
Journal:  Science       Date:  2010-04-30       Impact factor: 47.728

4.  Sn-zeolite beta as a heterogeneous chemoselective catalyst for Baeyer-Villiger oxidations.

Authors:  A Corma; L T Nemeth; M Renz; S Valencia
Journal:  Nature       Date:  2001-07-26       Impact factor: 49.962

5.  Theoretical study of 1,2-hydride shift associated with the isomerization of glyceraldehyde to dihydroxy acetone by Lewis acid active site models.

Authors:  Rajeev S Assary; Larry A Curtiss
Journal:  J Phys Chem A       Date:  2011-07-18       Impact factor: 2.781

6.  A kinetic estimate of the free aldehyde content of aldoses.

Authors:  J P Dworkin; S L Miller
Journal:  Carbohydr Res       Date:  2000-11-03       Impact factor: 2.104

7.  Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water.

Authors:  Manuel Moliner; Yuriy Román-Leshkov; Mark E Davis
Journal:  Proc Natl Acad Sci U S A       Date:  2010-03-22       Impact factor: 11.205

8.  Reactivity of Ti(IV) species hosted in TS-1 towards H2O2-H2O solutions investigated by ab initio cluster and periodic approaches combined with experimental XANES and EXAFS data: a review and new highlights.

Authors:  Silvia Bordiga; Francesca Bonino; Alessandro Damin; Carlo Lamberti
Journal:  Phys Chem Chem Phys       Date:  2007-07-25       Impact factor: 3.676

9.  Xylose isomerase in substrate and inhibitor michaelis states: atomic resolution studies of a metal-mediated hydride shift.

Authors:  Timothy D Fenn; Dagmar Ringe; Gregory A Petsko
Journal:  Biochemistry       Date:  2004-06-01       Impact factor: 3.162

10.  Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates.

Authors:  Yuriy Román-Leshkov; Christopher J Barrett; Zhen Y Liu; James A Dumesic
Journal:  Nature       Date:  2007-06-21       Impact factor: 49.962

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  16 in total

1.  Interrogating the Lewis Acidity of Metal Sites in Beta Zeolites with 15N Pyridine Adsorption Coupled with MAS NMR Spectroscopy.

Authors:  William R Gunther; Vladimir K Michaelis; Robert G Griffin; Yuriy Román-Leshkov
Journal:  J Phys Chem C Nanomater Interfaces       Date:  2016-09-21       Impact factor: 4.126

2.  Catalytic consequences of open and closed grafted Al(III)-calix[4]arene complexes for hydride and oxo transfer reactions.

Authors:  Partha Nandi; Wenjie Tang; Alexander Okrut; Xueqian Kong; Son-Jong Hwang; Matthew Neurock; Alexander Katz
Journal:  Proc Natl Acad Sci U S A       Date:  2013-01-28       Impact factor: 11.205

3.  Deprotonation and acidity characterization of biomass sugars: a first-principles study.

Authors:  Gang Yang; Chang Zhu; Lijun Zhou
Journal:  J Mol Model       Date:  2016-04-13       Impact factor: 1.810

4.  Radicalization and Radical Catalysis of Biomass Sugars: Insights from First-principles Studies.

Authors:  Gang Yang; Chang Zhu; Xianli Zou; Lijun Zhou
Journal:  Sci Rep       Date:  2016-07-13       Impact factor: 4.379

Review 5.  Recent progress in the development of solid catalysts for biomass conversion into high value-added chemicals.

Authors:  Michikazu Hara; Kiyotaka Nakajima; Keigo Kamata
Journal:  Sci Technol Adv Mater       Date:  2015-05-20       Impact factor: 8.090

6.  Competitive Adsorption of Substrate and Solvent in Sn-Beta Zeolite During Sugar Isomerization.

Authors:  William N P van der Graaff; Christiaan H L Tempelman; Guanna Li; Brahim Mezari; Nikolay Kosinov; Evgeny A Pidko; Emiel J M Hensen
Journal:  ChemSusChem       Date:  2016-10-28       Impact factor: 8.928

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

Authors:  William R Gunther; Yuran Wang; Yuewei Ji; Vladimir K Michaelis; Sean T Hunt; Robert G Griffin; Yuriy Román-Leshkov
Journal:  Nat Commun       Date:  2012       Impact factor: 14.919

8.  Identification of Active and Spectator Sn Sites in Sn-β Following Solid-State Stannation, and Consequences for Lewis Acid Catalysis.

Authors:  Ceri Hammond; Daniele Padovan; Abbas Al-Nayili; Peter P Wells; Emma K Gibson; Nikolaos Dimitratos
Journal:  ChemCatChem       Date:  2015-09-01       Impact factor: 5.686

9.  Dynamic nuclear polarization NMR enables the analysis of Sn-Beta zeolite prepared with natural abundance ¹¹⁹Sn precursors.

Authors:  William R Gunther; Vladimir K Michaelis; Marc A Caporini; Robert G Griffin; Yuriy Román-Leshkov
Journal:  J Am Chem Soc       Date:  2014-04-16       Impact factor: 15.419

10.  Selective Chemical Conversion of Sugars in Aqueous Solutions without Alkali to Lactic Acid Over a Zn-Sn-Beta Lewis Acid-Base Catalyst.

Authors:  Wenjie Dong; Zheng Shen; Boyu Peng; Minyan Gu; Xuefei Zhou; Bo Xiang; Yalei Zhang
Journal:  Sci Rep       Date:  2016-05-25       Impact factor: 4.379

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