C2 hydroxyl group governs the difference in hydrolysis rates of methyl-α-d-glycero-d-guloseptanoside and methyl-β-d-glycero-d- guloseptanoside

Journal of Organic Chemistry

Volumn 77, Issue 9, 2012, Pages 4242-4251

  Beck, Jeremy M ^a   Miller, Shawn M ^b   Peczuh, Mark W ^b   Hadad, Christopher M ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANOMERIC CARBON; ANOMERS; BOND CLEAVAGES; COMPUTATIONAL INVESTIGATION; COMPUTATIONAL STUDIES; CONFORMATIONAL ANALYSIS; ENERGY CONFORMATION; HYDROGEN BONDING INTERACTIONS; HYDROLYSIS RATE; HYDROXYL GROUPS; MODEL COMPOUND; MODEL SYSTEM; OXEPANE; OXOCARBENIUM; PYRANOSIDES; RING SYSTEMS; TRANSITION STATE;

CARBOHYDRATES; CONFORMATIONS; HYDROGEN BONDS; METHANOL; QUANTUM CHEMISTRY;

HYDROLYSIS;

CARBOHYDRATE DERIVATIVE; CARBON; HYDROXYL GROUP; METHANOL; METHYL ALPHA DEXTRO GLYCERO DEXTRO GULOSEPTANOSIDE; METHYL BETA DEXTRO GLYCERO DEXTRO GULOSEPTANOSIDE; OXEPANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; CONTROLLED STUDY; HYDROGEN BOND; HYDROLYSIS; PHASE TRANSITION;

COMPUTER SIMULATION; GLUCOSIDES; HYDROGEN BONDING; HYDROLYSIS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; THERMODYNAMICS;

EID: 84860630752     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202639g     Document Type: Article

References (51)

1. Freeze, H. Degradation and Turnover of Glycans. In Essentials of Glycobiology; Varki, A., Cummings, R., Esko, J., Freeze, H., Hart, G., Marth, J., Eds.; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 1999; pp 267-284.
2. http://www.cazy.org/.
3. Cantarel, B. L.; Coutinho, P. M.; Rancurel, C.; Bernard, T.; Lombard, V.; Henrissat, B. Nucleic Acids Res. 2009, 37, D233-D238
4. Davies, G.; Henrissat, B. Structure 1995, 3, 853-859
5. Kirby, A. J. Acc. Chem. Res. 1984, 17, 305-311
6. Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1999, 38, 750-770
7. Isoma, P.; Polaina, J.; Latorre-Garcia, L.; Canada, F. J.; Gonzalez, B.; Sanz-Aparicio, J. J. Mol. Biol. 2007, 371, 1204-1218
8. Gloster, T. M.; Roberts, S.; Ducros, V. M.-A.; Perugino, G.; Rossi, M.; Hoos, R.; Moracci, M.; Vasella, A.; Davies, G. J. Biochemistry 2004, 43, 6101-6109
9. Biarnés, X.; Nieto, J.; Planas, A.; Rovira, C. J. Biol. Chem. 2006, 281, 1432-1441
10. Biarnes, X.; Ardevol, A.; Planas, A.; Rovira, C. Biocatal. Biotransform. 2010, 28, 33-40
11. Deslongchamps, P. Intramolecular Strategies and Stereoelectronic Effects: Glycosides and Orthoesters Hydrolysis Revisited. In The Anomeric Effect and Associated Stereoelectronic Effects; Thatcher, G. R. J., Ed.; ACS Symposium Series 539: Washington, DC, 1993; pp 26-54.
12. Perrin, C. L. Anomeric Effects: An Iconoclastic View. In The Anomeric Effect and Associated Stereoelectronic Effects; Thatcher, G. R. J., Ed.; ACS Symposium Series 539: Washington, DC, 1993; pp 70-96.
13. Sinnott, M. L. No Kinetic Anomeric Effect in Reactions of Acetal Derivatives. In The Anomeric Effect and Associated Stereoelectronic Effects; Thatcher, G. R. J., Ed.; ACS Symposium Series 539: Washington, DC, 1993; pp 97-113.
14. Cocinero, E. J.; Carcabal, P.; Vaden, T. D.; Simons, J. P.; Davis, B. G. Nature 2011, 469, 76-80
15. DeMatteo, M. P.; Snyder, N. L.; Morton, M.; Baldisseri, D. M.; Hadad, C. M.; Peczuh, M. W. J. Org. Chem. 2005, 70, 24-38
16. DeMatteo, M. P.; Mei, S.; Fenton, R.; Morton, M.; Baldisseri, D. M.; Hadad, C. M.; Peczuh, M. W. Carbohydr. Res. 2006, 341, 2927-2945
17. Markad, S. D.; Miller, S. M.; Morton, M.; Peczuh, M. W. Tetrahedron Lett. 2010, 51, 1209-1212
18. Woods, R. J.; Andrews, C. W.; Bowen, J. P. J. Am. Chem. Soc. 1992, 114, 859-864
19. Andrews, C. W.; Fraser-Reid, B.; Bowen, J. P. J. Am. Chem. Soc. 1991, 113, 8293-8298
20. Deslongchamps, P.; Li., S.; Dory, Y. L. Org. Lett. 2004, 6, 505-508
21. van Eikeren, P. J. Org. Chem. 1985, 45, 4641-4645
22. Deslongchamps, P.; Dory, Y. L.; Li, S. Can. J. Chem. 1994, 72, 2021-2027
23. Bérces, A.; Enright, G.; Nukada, T.; Whitfield, D. M. J. Am. Chem. Soc. 2001, 123, 5460-5464
24. Stubbs, J. M.; Marx, D. Chem.-Eur. J. 2005, 11, 2651-2659
25. Satoh, H.; Hansen, H. S.; Manabe, S.; van Gunsteren, W. F.; Hünenberger, P. H. J. Chem. Theory Comput. 2010, 6, 1783-1797
26. Namchuck, M. N.; McCarter, J. D.; Becalski, A.; Andrews, T.; Withers, S. G. J. Am. Chem. Soc. 2000, 122, 1270-1277
27. Mega, T.; Matsushima, Y. J. Biochem. 1983, 94, 1637-1647
28. Withers, S. G.; Percival, M. D.; Street, I. P. Carbohydr. Res. 1989, 187, 43-66
29. Withers, S. G.; MacLennan, D. J.; Street, I. P. Carbohydr. Res. 1986, 154, 127-144
30. Edward, J. T. Chem. Ind. 1955, 1102-1104
31. Bennet, A.; Sinnott, M. L. J. Am. Chem. Soc. 1986, 108, 7287-7294
32. Sinnott, M. L.; Jencks, W. P. J. Am. Chem. Soc. 1980, 102, 2026-2032
33. Baker., F. W.; Parish, R. C.; Stock., L. M. J. Am. Chem. Soc. 1967, 89, 5677-5685
34. Capon, B. Chem. Rev. 1969, 69, 407-498 and cited references.
35. Molecular Operating Environment, version 2007.09; Chemical Computing Group: Montreal, Quebec, Canada, 2007.
36. Halgren, T. A. J. Comput. Chem. 1996, 17, 490-641
37. Halgren, T. A. J. Comput. Chem. 1999, 20, 720-729
38. Halgren, T. A. J. Comput. Chem. 1999, 20 730-741.
39. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision A.1; Gaussian, Inc.: Wallingford CT, 2009.
40. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377
41. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1998, 37, 785-789
42. Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 16, 217-219
43. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327-335
44. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396
45. Hratchian, H. P.; Schlegel, H. B. J. Chem. Theory Comput. 2005, 1, 61-69
46. National Institute of Standards and Technology, http://srdata.nist.gov/ ccbdb.
47. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
48. Zhao, Y.; Truhlar, D. G. Org. Lett. 2006, 8, 5753-5755
49. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Theory Comput. 2006, 364-382
50. Csonka, G. I.; French, A. D.; Johnson, G. P.; Stortz, C. A. J. Chem. Theory Comput. 2009, 5, 679-692
51. Cramer, C. J.; Truhlar, D. G.; French, A. D. Carbohydr. Res. 1997, 298, 1-14