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A pronounced kinetic isotope effect (KIE) was observed if the deuterium label was at the C2 position, thus suggesting that a hydrogen shift from the C2 to C1 positions was the rate\u2010limiting step with the three catalysts. <jats:sup>13<\/jats:sup>C and <jats:sup>1<\/jats:sup>H\u2005NMR spectroscopic investigations confirmed that an intra\u2010hydride\u2010transfer reaction pathway was the predominant reaction channel for all three catalysts in aqueous media. Furthermore, the deuterium atom in the labeled glucose could be mapped onto hydroxymethylfurfural and formic acid through reactions that followed the isomerization step in the presence of Br\u00f8nsted acids. In all three catalysts, the active site appeared to be a bifunctional Lewis\u2010acidic\/Br\u00f8nsted\u2010basic site, based on a speciation model and first\u2010principles calculations. For the first time, a mechanistic similarities between the homogeneous and heterogeneous catalysis of aldose\u2010to\u2010ketose isomerization is established and it is suggested that learning from homogeneous catalysis could assist in the development of improved heterogeneous catalysts.<\/jats:p>","DOI":"10.1002\/cssc.201300328","type":"journal-article","created":{"date-parts":[[2013,10,8]],"date-time":"2013-10-08T08:02:36Z","timestamp":1381219356000},"page":"2369-2376","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":157,"title":["Comparison of Homogeneous and Heterogeneous Catalysts for Glucose\u2010to\u2010Fructose Isomerization in Aqueous Media"],"prefix":"10.1002","volume":"6","author":[{"given":"Vinit","family":"Choudhary","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ana B.","family":"Pinar","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Raul F.","family":"Lobo","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dionisios G.","family":"Vlachos","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stanley I.","family":"Sandler","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,9,17]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.biombioe.2012.03.016"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300182k"},{"key":"e_1_2_6_4_2","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2ra21811a"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/b925869h"},{"key":"e_1_2_6_7_2","doi-asserted-by":"crossref","first-page":"17","DOI":"10.3998\/ark.5550190.0002.102","volume":"2","author":"Lewkowski J.","year":"2001","journal-title":"ARKIVOC"},{"key":"e_1_2_6_8_2","unstructured":"\u00a0"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1002358107"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs300265d"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs300192z"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201100688"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp2113895"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi049812o"},{"key":"e_1_2_6_15_2","unstructured":"\u00a0"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1141199"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100171a"},{"key":"e_1_2_6_18_2","unstructured":"\u00a0"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja808537j"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201000181"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11244-012-9826-y"},{"key":"e_1_2_6_22_2","unstructured":"\u00a0"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1126337"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0gc00639d"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs2000544"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201000250"},{"key":"e_1_2_6_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201000250"},{"key":"e_1_2_6_27_2","unstructured":"\u00a0"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11244-010-9570-0"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.biortech.2012.03.126"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja3122763"},{"key":"e_1_2_6_31_2","unstructured":"\u00a0"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs200461t"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2ra21381h"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1007\/3-540-44422-X_1"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja961259d"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00296a004"},{"key":"e_1_2_6_37_2","unstructured":"\u00a0"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0065-2318(08)60411-4"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0008-6215(97)00058-X"},{"key":"e_1_2_6_40_2","first-page":"183","volume":"26","author":"Bilik V.","year":"1972","journal-title":"Chem. 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