FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2045642859> ?p ?o ?g. }

• W2045642859 endingPage "1476" @default.
• W2045642859 startingPage "1469" @default.
• W2045642859 abstract "Pure-silica zeolite beta containing Lewis acidic framework Ti4+ centers (Ti-Beta) is shown to catalyze the isomerization of d-glucose to l-sorbose via an intramolecular C5–C1 hydride shift. Glucose–sorbose isomerization occurs in parallel to glucose–fructose isomerization on Ti-Beta in both water and methanol solvents, with fructose formed as the predominant product in water and sorbose as the predominant product in methanol (at 373 K) at initial times and over the course of >10 turnovers. Isotopic tracer studies demonstrate that 13C and D labels placed respectively at the C1 and C2 positions of glucose are retained respectively at the C6 and C5 positions of sorbose, consistent with its formation via an intramolecular C5–C1 hydride shift isomerization mechanism. This direct Lewis acid-mediated pathway for glucose–sorbose isomerization appears to be unprecedented among heterogeneous or biological catalysts and sharply contrasts indirect base-mediated glucose–sorbose isomerization via 3,4-enediol intermediates or via retro-aldol fragmentation and recombination of sugar fragments. Measured first-order glucose–sorbose isomerization rate constants (per total Ti; 373 K) for Ti-Beta in methanol are similar for glucose and glucose deuterated at the C2 position (within a factor of ∼1.1), but are a factor of ∼2.3 lower for glucose deuterated at each carbon position, leading to H/D kinetic isotope effects expected for kinetically relevant intramolecular C5–C1 hydride shift steps. Optical rotation measurements show that isomerization of d-(+)-glucose (92% enantiomeric purity) with Ti-Beta in water (373 K) led to the formation of l-(−)-sorbose (73% enantiomeric purity) and d-(−)-fructose (87% enantiomeric purity) as the predominant stereoisomers, indicating that stereochemistry is preserved at carbon centers not directly involved in intramolecular C5–C1 or C2–C1 hydride shift steps, respectively. This new Lewis acid-mediated rearrangement of glucose to sorbose does not appear to have a metalloenzyme analog." @default.
• W2045642859 created "2016-06-24" @default.
• W2045642859 creator A5010404427 @default.
• W2045642859 creator A5072511676 @default.
• W2045642859 date "2013-06-03" @default.
• W2045642859 modified "2023-10-16" @default.
• W2045642859 title "Titanium-Beta Zeolites Catalyze the Stereospecific Isomerization of <scp>d</scp>-Glucose to <scp>l</scp>-Sorbose via Intramolecular C5–C1 Hydride Shift" @default.
• W2045642859 cites W113517929 @default.
• W2045642859 cites W1586372951 @default.
• W2045642859 cites W1995315995 @default.
• W2045642859 cites W1999992131 @default.
• W2045642859 cites W2001210063 @default.
• W2045642859 cites W2001319130 @default.
• W2045642859 cites W2001347858 @default.
• W2045642859 cites W2005014839 @default.
• W2045642859 cites W2019704353 @default.
• W2045642859 cites W2020720383 @default.
• W2045642859 cites W2021341365 @default.
• W2045642859 cites W2026100982 @default.
• W2045642859 cites W2029641302 @default.
• W2045642859 cites W2039120214 @default.
• W2045642859 cites W2060675608 @default.
• W2045642859 cites W2068654934 @default.
• W2045642859 cites W2069612873 @default.
• W2045642859 cites W2076237586 @default.
• W2045642859 cites W2077279509 @default.
• W2045642859 cites W2083210056 @default.
• W2045642859 cites W2096605011 @default.
• W2045642859 cites W2109715305 @default.
• W2045642859 cites W2127381875 @default.
• W2045642859 cites W2133134312 @default.
• W2045642859 cites W2145629361 @default.
• W2045642859 cites W22461807 @default.
• W2045642859 cites W2324003949 @default.
• W2045642859 cites W2327836111 @default.
• W2045642859 cites W2328328583 @default.
• W2045642859 cites W2460535487 @default.
• W2045642859 cites W4239337538 @default.
• W2045642859 cites W42406836 @default.
• W2045642859 cites W4240743811 @default.
• W2045642859 doi "https://doi.org/10.1021/cs400273c" @default.
• W2045642859 hasPublicationYear "2013" @default.
• W2045642859 type Work @default.
• W2045642859 sameAs 2045642859 @default.
• W2045642859 citedByCount "56" @default.
• W2045642859 countsByYear W20456428592013 @default.
• W2045642859 countsByYear W20456428592014 @default.
• W2045642859 countsByYear W20456428592015 @default.
• W2045642859 countsByYear W20456428592016 @default.
• W2045642859 countsByYear W20456428592017 @default.
• W2045642859 countsByYear W20456428592018 @default.
• W2045642859 countsByYear W20456428592019 @default.
• W2045642859 countsByYear W20456428592020 @default.
• W2045642859 countsByYear W20456428592021 @default.
• W2045642859 countsByYear W20456428592022 @default.
• W2045642859 countsByYear W20456428592023 @default.
• W2045642859 crossrefType "journal-article" @default.
• W2045642859 hasAuthorship W2045642859A5010404427 @default.
• W2045642859 hasAuthorship W2045642859A5072511676 @default.
• W2045642859 hasConcept C121332964 @default.
• W2045642859 hasConcept C126661725 @default.
• W2045642859 hasConcept C155647269 @default.
• W2045642859 hasConcept C161790260 @default.
• W2045642859 hasConcept C178790620 @default.
• W2045642859 hasConcept C185592680 @default.
• W2045642859 hasConcept C2776970464 @default.
• W2045642859 hasConcept C2779638233 @default.
• W2045642859 hasConcept C58364064 @default.
• W2045642859 hasConcept C62520636 @default.
• W2045642859 hasConcept C69928629 @default.
• W2045642859 hasConcept C71240020 @default.
• W2045642859 hasConcept C75079739 @default.
• W2045642859 hasConcept C75473681 @default.
• W2045642859 hasConceptScore W2045642859C121332964 @default.
• W2045642859 hasConceptScore W2045642859C126661725 @default.
• W2045642859 hasConceptScore W2045642859C155647269 @default.
• W2045642859 hasConceptScore W2045642859C161790260 @default.
• W2045642859 hasConceptScore W2045642859C178790620 @default.
• W2045642859 hasConceptScore W2045642859C185592680 @default.
• W2045642859 hasConceptScore W2045642859C2776970464 @default.
• W2045642859 hasConceptScore W2045642859C2779638233 @default.
• W2045642859 hasConceptScore W2045642859C58364064 @default.
• W2045642859 hasConceptScore W2045642859C62520636 @default.
• W2045642859 hasConceptScore W2045642859C69928629 @default.
• W2045642859 hasConceptScore W2045642859C71240020 @default.
• W2045642859 hasConceptScore W2045642859C75079739 @default.
• W2045642859 hasConceptScore W2045642859C75473681 @default.
• W2045642859 hasIssue "7" @default.
• W2045642859 hasLocation W20456428591 @default.
• W2045642859 hasOpenAccess W2045642859 @default.
• W2045642859 hasPrimaryLocation W20456428591 @default.
• W2045642859 hasRelatedWork W2086191285 @default.
• W2045642859 hasRelatedWork W2320277076 @default.
• W2045642859 hasRelatedWork W2363498292 @default.
• W2045642859 hasRelatedWork W2395773616 @default.
• W2045642859 hasRelatedWork W2397405551 @default.
• W2045642859 hasRelatedWork W2605206679 @default.
• W2045642859 hasRelatedWork W2949226866 @default.

• next