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

Scientific Reports

Volumn 6, Issue , 2016, Pages

  Yang, Gang ^a   Zhu, Chang ^a   Zou, Xianli ^a   Zhou, Lijun ^a  

^a SOUTHWEST UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84978890735     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep29711     Document Type: Article

References (59)

1. Mäki-Arvela, P., Simakova, I. L., Salmi, T. & Murzi. D. Y. Production of lactic acid/lactates from biomass and their catalytic transformations to commodities. Chem. Rev. 114, 1909-1971 (2014).
2. Bermejo-Deval, R. et al. Metalloenzyme-like catalyzed isomerizations of sugars by Lewis acid zeolites. Proc. Natl. Acd. Sci. USA 109, 9727-9732 (2012).
3. Holm, M. S., Saravanamurugan, S. & Taarning, E. Conversion of sugars to lactic acid derivatives using heterogeneous zeotype catalysts. Science 328, 602-605 (2010).
4. Caratzoulas, S. et al. Challenges of and insights into acid-catalyzed transformations of sugars. J. Phys. Chem. C 118, 22815-22833 (2014).
5. Zhao, H. B., Holladay, J. E., Brown, H. & Zhang, Z. C. Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural. Science 316, 1597-1600 (2007).
6. Hu, S. Q., Zhang, Z. F., Song, J. L., Zhou, Y. X. & Han, B. X. Efficient conversion of glucose into 5-hydroxymethylfurfural catalyzed by a common Lewis acid SnCl4 in an ionic liquid. Green Chem. 11, 1746-1749 (2009).
7. Moliner, M., Román-Leshkov, Y. & Davis, M. E. Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water. Proc. Natl. Acd. Sci. USA 107, 6164-6168 (2010).
8. Pidko, E. A., Degirmenci, V., van Santen, R. A. & Hensen, E. J. M. Glucose activation by transient Cr2+ dimers. Angew. Chem. Int. Ed. 49, 2530-2534 (2010).
9. Bermejo-Deval, R. et al. Metalloenzyme-like catalyzed isomerizations of sugars by Lewis acid zeolites. Proc. Natl. Acd. Sci. USA 109, 9727-9732 (2012).
10. Yang, G., Pidko, E. A. & Hensen, E. J. M. The mechanism of glucose isomerization to fructose over Sn-BEA zeolite: A periodic density functional theory study. ChemSusChem 6, 1688-1696 (2013).
11. Rai, N., Caratzoulas, S. & Vlachos, D. G. Role of Silanol group in Sn-Beta zeolite for glucose isomerization and epimerization reactions. ACS Catal. 3, 2294-2298 (2013).
12. Li, Y. P., Head-Gordon, M. & Bell, A. T. Analysis of the reaction mechanism and catalytic activity of metal-substituted beta zeolite for the isomerization of glucose to fructose. ACS Catal. 4, 1537-1545 (2014).
13. Chethana, B. K. & Mushrif, S. H. Brønsted and Lewis acid sites of Sn-beta zeolite, in combination with the borate salt, catalyze the epimerization of glucose: A density functional theory study. J. Catal. 323, 158-164 (2015).
14. Christianson, J. R., Caratzoulas, S. & Vlachos, D. G. Computational insight into the effect of Sn-beta Na exchange and solvent on glucose isomerization and epimerization. ACS Catal. 5, 5256-5263 (2015).
15. 2. ChemSusChem 8, 2907-2916 (2015).
16. Yang, G., Pidko, E. A. & Hensen, E. J. M. Mechanism of Brønsted acid catalyzed conversion of carbohydrates. J. Catal. 295, 122-132 (2012).
17. Qian, X. H., Nimlos, M. R., Davis, M., Johnson, D. K. & Himmel, M. E. Ab initio molecular dynamics simulations of β-D-glucose and β-D-xylose degradation mechanisms in acidic aqueous solution. Carbohydrate Res. 340, 2319-2327 (2005).
18. Qian, X. H., Johnson, D. K., Himmel, M. E. & Nimlos, M. R. The role of hydrogen-bonding interactions in acidic sugar reaction pathways. Carbohydrate Res. 345, 1945-1951 (2010).
19. Nikolla, E., Román-Leshkov, Y., Moliner, M. & Davis, M. E. "One-pot" synthesis of 5-(hydroxymethyl)furfural from carbohydrates using Tin-beta zeolite. ACS Catal. 1, 408-410 (2011).
20. Salpin, J. Y. & Tortajada, J. Gas-phase acidity of D-glucose. A density functional theory study. J. Mass Spectrom. 39, 930-941 (2004).
21. Feng, S. T., Bagia, C. & Mpourmpakis, G. Determination of proton affinities and acidity constants of sugars. J. Phys. Chem. A 117, 5211-5219 (2013).
22. Woods, R. J., Szarek, W. A. & Vedene, H. S., Jr. The proton affinities and deprotonation enthalpies of D-fructopyranose and L-sorbopyranose. Can. J. Chem. 69, 1917-1928 (1991).
23. Flosadottir, H. D., Bald, I. & Ingólfsson, O. Fast and metastable fragmentation of deprotonated D-fructose-A combined experimental and computational study. Int. J. Mass Spectrom. 305, 50-57 (2011).
24. Liu, C. et al. Selective base-catalyzed isomerization of glucose to fructose. ACS Catal. 4, 4295-4298 (2014).
25. Mukherjee, S. & List, B. Organic chemistry: Radical catalysis. Nature 447, 152-153 (2007).
26. Studer, A. & Curran, D. P. Catalysis of radical reactions: A radical chemistry perspective. Angew. Chem. Int. Ed. 55, 58-102 (2016).
27. Vanhaelewyn, G. et al. Electron magnetic resonance study of stable radicals in irradiated D-fructose single crystals. Phys. Chem. Chem. Phys. 3, 1729-1735 (2001).
28. Pauwels, E., van Speybroeck, V. & Waroquier, M. Radiation-induced radicals in α-D-glucose: Comparing DFT cluster calculations with magnetic resonance experiments. Spectrochim. Acta Part A 63, 795-801 (2006).
29. Tarpan, M. A., Pauwels, E., Vrielinck, H., Waroquier, M. & Callens, F. Electron magnetic resonance and density functional theory study of room temperature X-irradiated D-fructose single crystals. J. Phys. Chem. A 114, 12417-12426 (2010).
30. Kusakovskij, J., Callens, F. & Vrielinck, H. EMR study and DFT-assisted identification of transient radicals in X-irradiated crystalline sucrose. J. Phys. Chem. B 119, 6562-6570 (2015).
31. Pauwels, E. et al. Tentative structures for the radiation-induced radicals in crystalline β-D-fructose using density functional theory. J. Phys. Chem. A 106, 12340-12348 (2002).
32. Declerck, R., Pauwels, E., van Speybroeck, V. & Waroquier, M. Molecular environment and temperature dependence of hyperfine interactions in sugar crystal radicals from first principles. J. Phys. Chem. B 112, 1508-1514 (2008).
33. Croft, A. K., Easton, C. J. & Radom, L. Design of radical-resistant amino acid residues: A combined theoretical and experimental investigation. J. Am. Chem. Soc. 125, 4119-4124 (2003).
34. Yang, G., Zu, Y. G. & Zhou, L. Deprotonation and radicalization of glycine neutral structures. J. J. Phys. Org. Chem. 21, 34-40 (2008).
35. Hioe, J. & Zipse, H. Radical stability and its role in synthesis and catalysis. Org. Biomol. Chem. 8, 3609-3617 (2010).
36. Jebber, K. A., Zhang, K., Cassady, C. J. & Chung-Phillips, A. Ab initio and experimental studies on the protonation of glucose in the gas phase. J. Am. Chem. Soc. 118, 10515-10524 (1996).
37. Liu, D. J., Nimlos, M. R., Johnson, D. K., Himmel, M. E. & Qian, X. H. Free energy landscape for glucose condensation reactions. J. Phys. Chem. A 114, 12936-12944 (2010).
38. Jadhav, H., Pedersen, C. M., Sølling, T. & Bols, M. 3-Deoxy-glucosone is an intermediate in the formation of furfurals from D-glucose. ChemSusChem 4, 1049-1051 (2011).
39. Csonka, G. I., French, A. D., Johnson, G. P. & Stortz, C. A. Evaluation of density functionals and basis sets for carbohydrates. J. Chem. Theory Comput. 5, 679-692 (2009).
40. Li, D. M., Huang, X. Q., Han, K. L. & Zhan, C. G. Catalytic mechanism of cytochrome P450 for 5'-hydroxylation of nicotine: Fundamental reaction pathways and stereoselectivity. J. Am. Chem. Soc. 133, 7416-7427 (2011).
41. Li, D. M., Wang, Y. & Han, K. L. Recent density functional theory model calculations of drug metabolism by cytochrome P450. Coordination Chem. Rev. 256, 1137-1150 (2012).
42. Gaussian 09, Revision D.01, Frisch, M.J. et al. Gaussian, Inc., Wallingford CT (2013).
43. Roothaan, C. C. J. New developments in molecular orbital theory. Rev. Mod. Phys. 23, 69-89 (1951).
44. Becke, A. D. A Multicenter numerical integration scheme for polyatomic molecules. J. Chem. Phys. 88, 2547-2551 (1988).
45. Lee, C., Yang, W. T. & Parr, R. G. Development of the Colle-Salvetti correlation energy formula into a functional of the electron density. Phys. Rev. B 37, 785-789 (1988).
46. Perdew, J. P. Density-functional approximation for the correlation energy of the inhomogeneous electron gas. Phys. Rev. B 33, 8822-8824 (1986).
47. Adamo, C. & Barone, V. Toward reliable density functional methods without adjustable parameters: The PBE0 model. J. Chem. Phys. 110, 6158-6169 (1999).
48. Zhao, Y. & Truhlar, D. G. A new local density functional for main-group thermochemistry, transition metal bonding, thermochemical kinetics, and noncovalent interactions. J. Chem. Phys. 125, 194101 (2006).
49. Zhao, Y. & Truhlar, D. G. The M06 Suite of Density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: Two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor. Chem. Acc. 120, 215-241 (2008).
50. Tomasi, J., Mennucci, R. & Cammi, R. Quantum Mechanical Continuum Solvation Models. Chem. Rev. 105, 2999-3093 (2005).
51. Lundberg, M., Kawatsu, T., Vreven, T., Frisch, M. J. & Morokuma, K. Transition states in a protein environment-ONIOM QM:MM modeling of isopenicillin N synthesis. J. Chem. Theory Comput. 5, 222-234 (2009).
52. Chung, L W. et al. The ONIOM nethod and its applications. Chem. Rev. 115, 5678-5796 (2015).
53. Alonso, J. L. et al. The conformational behavior of free D-glucose-At last. Chem. Sci. 5, 515-522 (2014).
54. Yang, G., Li, X. & Zhou, L. J. Adsorption of fructose in Sn-BEA zeolite from periodic density functional calculations. RSC Adv. 6, 8838-8847 (2016).
55. Curtiss, L. A., Redfern, P. C. & Raghavachari, K. Gaussian-4 theory using reduced order perturbation theory. J. Chem. Phys. 127, 124105 (2007).
56. Rankin, K. N., Gauld, J. W. & Boyd, R. J. Density functional study of the proline-catalyzed direct aldol reaction. J. Phys. Chem. A 106, 5155-5159 (2002).
57. Yang, G., Yang, Z. W., Zhou, L. J., Zhu, R. X. & Liu, C. B. A revisit to proline-catalyzed aldol reaction: Interactions with acetone and catalytic mechanisms. J. Mol. Catal. A: Chemistry 316, 112-117 (2010).
58. Tang, S., Liu, K., Liu, C. & Lei, A. W. Olefinic C-H functionalization through radical alkenylation. Chem. Soc. Rev. 44, 1070-1082 (2015).
59. Yang, L., Tsilomelekis, G., Caratzoulas, S. & Vlachos, D. G. Mechanism of Brønsted acid-catalyzed glucose dehydration. ChemSusChem 8, 1334-1341 (2015).