Conformational analysis of thiosugars: Theoretical NMR chemical shifts and 3JH,H coupling constants of 5-thio-pyranose monosaccharides

Journal of Carbohydrate Chemistry

Volumn 25, Issue 7, 2006, Pages 557-594

  Aguirre valderrama, Alonso ^a   Dobado, José A ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

5 Thio sugars; 5 Thiopyranoses; Conformational analysis; Thiopyranoses; Thiosugars

Indexed keywords

EID: 33750508755     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328300600966471     Document Type: Article

References (62)

1. Ganem, B. Inhibitors of carbohydrate-processing enzymes: design and synthesis of sugar-shaped heterocycles. Acc. Chem. Res. 1996, 29, 340-347.
2. Yuasa, H.; Saotome, C.; Kanie, O. Design syntheses of inhibitors of glycoenzymes. Trends Glycosci. Glyc. 2002, 14, 231-251.
3. Simanek, E.E.; McGarvey, G.J.; Jablonowski, J.A.; Wong, C.H. Selectin-carbohydrate interactions: from natural ligands to designed mimics. Chem. Rev. 1998, 98, 833-862.
4. Sears, P.; Wong, C.H. Carbohydrate mimetics: a new strategy for tackling the problem of carbohydrate-mediated biological recognition. Angew. Chem. Int. Ed. 1999, 38, 2300-2324.
5. Yuasa, H.; Hashimoto, H. Recent advances in the development of unnatural oligosaccharides. Conformation and bioactivity. Trends Glycosci. Glyc. 2001, 13, 31-55.
6. Atsushi, K.; Noriko, K.; Erika, K.; Isao, A.; Kyoko, I.; Liang, Y.; Tadashi, O.; Yasunori, B.; Hidekazu, O.; Hiroki, T.; Naoki, A. Biological properties of D- and L-1-deoxyazasugars. J. Med. Chem. 2005, 48, 2036-2044.
7. Yuasa, H.; Hashimoto, H. Replacing the ring oxygen of carbohydrates with sulfur: its biological and chemical consequences. Rev. Heteroatom. Chem. 1999, 19, 35-65.
8. Fernández-Bolaños, J.G.; Al-Masoudi, N.A.L.; Maya, I. Sugar derivatives having sulfur in the ring. Adv. Carbohydr. Chem. Biochem. 2001, 57, 21-98.
9. Robina, I.; Vogel, P.; Witczak, Z.J. Synthesis and biological properties of monothiosaccharides. Curr. Org. Chem. 2001, 5, 1177-1214.
10. Paulsen, H.; Todt, K. Cyclic monosaccharides having nitrogen or sulfur in the ring. Adv. Carbohydr. Chem. 1968, 23, 115-232.
11. Robina, I.; Vogel, P. The synthesis of disaccharides, oligosaccharides and analogues containing thiosugars. Curr. Org. Chem. 2002, 6, 471-491.
12. Tsuruta, O.; Yuasa, H.; Hashimoto, H.; Sujino, K.; Otter, A.; Li, H.; Palcic, M.M. Synthesis of GDP-5-thiosugars and their use as glycosyl donor substrates for glycosyltransferases. J. Org. Chem. 2003, 68, 6400-6406.
13. Schwarz, J.C.P.; Yule, K.C. D-xylothiapyranose - a sugar with sulphur in ring. Proc. Chem. Soc. 1961, 417.
14. Adley, T.J.; Owen, L.N. Thio-sugars with sulphur in ring. Proc. Chem. Soc. 1961, 418.
15. Whistler, R.L.; Nayak, U.G. Improved syntheses of 5-thio-D-glucose. J. Org. Chem. 1969, 34, 97-100.
16. β. Biochem. Pharmacol. 1973, 22, 29-35.
17. Kim, J.H.; Kim, S.H.; Han, E.W.; Song, C.W. 5-Thio-D-glucose selectivity potentiates hyperthermia killing of hypoxic tumor-cells. Science 1978, 200, 206-207.
18. Inamori, Y.; Muro, C.; Toyoda, M.; Kato, Y.; Tsujibo, H. Inhibitory activity of 5-thio-D-glucose on plant-growth. Biosci. Biotech. Biochem. 1994, 58, 1877-1878.
19. Izumi, M.; Tsuruta, O.; Hashimoto, H. A facile synthesis of 5-thio-L-fucose and 5-thio-D-arabinose from D-arabinose. Carbohydr. Res. 1996, 280, 287-302.
20. Hashimoto, H.; Kawanishi, M.; Yuasa, H. Novel conversion of aldopyranosides into 5-thioaldopyranosides via acyclic monthioacetals with inversion and retention of configuration at C-5. Carbohydr. Res. 1996, 282, 207-221.
21. Le Merrer, Y.; Fuzier, M.; Dosbaa, I.; Foglietti, M.J.; Depezay, J.C. Synthesis of thiosugars as weak inhibitors of glycosidases. Tetrahedron 1997, 53, 16731-16746.
22. Cubero, I.I.; López-Espinosa, M.T.P.; Richardson, A.C.; Ortega, M.D.S. Enantiospecific synthesis of 1-deoxythiomannojirimycin from a derivative of D-glucose. Carbohydr. Res. 1993, 242, 109-118.
23. Yuasa, H.; Izukawa, Y.; Hashimoto, H. Synthesis of 5-thio-D-mannose. J. Carbohydr. Chem. 1989, 8, 753-763.
24. Capon, R.J.; MacLeod, J.K. 5-Thio-D-mannose from the marine sponge Clathria Pyramida (Lendenfeld). The first example of a naturally occurring 5-thiosugar. J. Chem. Soc., Chem. Commun. 1987, 1200-1201.
25. Yuasa, H.; Takada, J.; Hashimoto, H. Synthesis of salacinol. Tetrahedron Lett. 2000, 41, 6615-6618.
26. Imberty, A.; Pérez, S. Structure, conformation, and dynamics of bioactive oligosaccharides: theoretical approaches and experimental validations. Carbohydr. Res. 2000, 100, 4567-4588.
27. Panday, N.; Meyyappan, M.; Vasella, A. A comparison of glucose- and glucosamine-related inhibitors: probing the interaction of the 2-hydroxy group with retaining β-glucosidases. Helv. Chim. Acta 2000, 83, 513-538.
28. Wormald, M.R.; Petrescu, A.J.; Pao, Y.; Glithero, A.; Elliott, T.; Dwek, R.A. Conformational studies of oligosaccharides and glycopeptides: complementarity of NMR, X-ray crystallography, and molecular modelling. Chem. Rev. 2002, 102, 371-386.
29. The anomeric effect has been explained by decreasing the dipole-dipole repulsion between C-O bonds in the axial anomer (Edward, J.T. Stability of glycosides to acid hydrolysis - a conformational analysis. Chem. Ind. (London) 1955, 36, 1102-1104.
30. Anderson, C.B.; Sepp, D.T Conformation and the anomeric effect in 2-oxy-substituted tetrahydropyrans. Tetrahedron 1968, 24, 1707-1716)
31. and/or from greater hyperconjugative stabilization of pyranose oxygen lone-pair density, when delocalized into the empty axial σ*CO orbital (Romers, C.; Altona, C.; Buys, H.R.; Havinga E. In Topics in Stereochemistry; Eliel, E.L., Allinger, N.L., Eds.; Wiley: New York, 1969; Vol. 4, 39).
32. Woods, R.J.; Smith, J.V.H.; Szarek, W.A.; Farazdel, A. Ab initio LCAO-MO calculations on α-D-glucopyranose, β-D-fructopyranose, and their thiopyranoid-ring analogues. Application to a theory of sweetness. J. Chem. Soc., Chem. Commun. 1987, 937-939.
33. Kavlekar, L.M.; Kuntz, D.A.; Wen, X.; Jonshton, B.D.; Svensson, B.; Rose, D.R.; Mario Pinto, B. 5-Thio-D-glycopyranosylamines and their amidinium salts as potential transition-state mimics of glycosyl hydrolases: synthesis, enzyme inhibitory activities, X-ray crystallography, and molecular modeling. Tetrahedron: Asymm. 2005, 16, 1035-1046.
34. Wong, C.H. Mimics of complex carbohydrates recognized by receptors. Acc. Chem. Res. 1999, 32, 376-385.
35. Calvo-Flores, F.G.; García-Mendoza, P.; Hernández-Mateo, F.; Isac-García, J.; Santoyo-González, F. Applications of cyclic sulfates of vic-diols: synthesis of episulfides, olefins, and thio sugars. J. Org. Chem. 1997, 62, 3944-3961.
36. 4 α-L-fucose. J. Comput. Chem. 1996, 18, 330-342.
37. 1 chair forms of β-D-glucose: a density functional study. Chem. Phys. Lett. 1996, 257, 49-60.
38. Lemieux, R.U. How water provides the impetus for molecular recognition in aqueous solution. Acc. Chem. Res. 1996, 29, 373-380.
39. Tomasi, J.; Persico, M. Molecular interactions in solution: an overview of methods based on continuous distributions of the solvent. Chem. Rev. 1994, 94, 2027-2094.
40. Cramer, C.J.; Truhlar, D.G. Implicit solvation models: equilibria, structure, spectra, and dynamics. Chem. Rev. 1999, 99, 2161-2200.
41. Duus, J.Ø.; Gotfredsen, C.H.; Bock, K. Carbohydrate structural determination by NMR spectroscopy: modern methods and limitations. Chem. Rev. 2000, 100, 4589-4614.
42. Herfurth, L.; Weimar, T.; Peters, T. Application of 3D-TOCSY-trNOESY for the assignment of bioactive ligands from mixtures. Angew. Chem. Int. Ed. 2000, 39, 2097-2099.
43. Helgaker, T.; Watson, M.; Handy, N.C. Analytical calculation of nuclear magnetic resonance indirect spin-spin coupling constants at the generalized gradient approximation and hybrid levels of density-functional theory. J. Chem. Phys. 2000, 113, 9402-9409.
44. Sychrovský, V.; Gräfenstein, J.; Cremer, D. Nuclear magnetic resonance spin-spin coupling constants from coupled perturbed density functional theory. J. Chem. Phys. 2000, 113, 3530-3547.
45. Haassnoot, C.A.G.; De-Leeuw, F.A.A.M.; Altona, C. The relationship between proton-proton NMR coupling constants and substituent electronegativities-I (an empirical generalization of the Karplus equation). Tetrahedron 1980, 36, 2783-2792.
46. 2 torsional terms. J. Am. Chem. Soc. 1977, 99, 8127-8134)
47. and MMP1 programs (Allinger, N.L.; Sprague, J.T. Calculation of the structures of hydrocarbons containing delocalized electronic systems by the molecular mechanics method. J. Am. Chem. Soc. 1973, 95, 3893-3907) by Gajewski and Gilbert implemented in the PCMODEL program (available on Serena Software, PO Box, 3076, Bloomington, IN 47402-3076, USA).
48. We used the Cremer and Pople puckering coordinates algorithm (see Cremer, D.; Pople, J.A A general definition of ring puckering coordinates. J. Am. Chem. Soc. 1975, 97, 1354-1358) to classify the ring form.
49. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Montgomery, J.A., Jr.; Vreven, T.; Kudin, K.N.; Burant, J.C.; Millam, J.M.; Iyengar, S.S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G.A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J.E.; Hratchian, H.P.; Cross, J.B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Ayala, P.Y.; Morokuma, K.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Zakrzewski, V.G.; Dapprich, S.; Daniels, A.D.; Strain, M.C.; Farkas, O.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Ortiz, J.V.; Cui, Q.; Baboul, A.G.; Clifford, S.; Cioslowski, J.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M.W.; Johnson, B.; Chen, W.; Wong, M.W.; Gonzalez, C. Gaussian 03, Revision B.05; Gaussian, Inc: Pittsburgh, PA, 2003.
50. Cramer, C.J.; Truhlar, D.G. Quantum chemical conformational analysis of glucose in aqueous solution. J. Am. Chem. Soc. 1993, 115, 5745-5753.
51. Stewart, J.J.P. Optimization of parameters for semiempirical methods I. Method. J. Comput. Chem. 1989, 10, 209-220.
52. Onsager, L. Electric moments of molecules in liquids. J. Am. Chem. Soc. 1936, 58, 1486-1493.
53. Wolinski, K.; Hinton, J.F.; Pulay, P. Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J. Am. Chem. Soc. 1990, 112, 8251-8260.
54. Csonka, G.I.; Élías, K.; Kolossváry, I.; Sosa, C.P.; Csizmadia, I.G. Theoretical study of alternative ring forms of α-L-fucopyranose. J. Phys. Chem. A 1998, 102, 1219-1229.
55. 4 ring form of 1 this situation is done for 1t orientation. The 1g+, one is non-exo, and the 1 g-, although it is exo, shows 1-3-diaxial-type repulsion with axial hydrogen on C3 and C5.
56. Mehta, S.; Jordan, K.L.; Weimar, T.; Kreis, U.C.; Batchelor, R.J.; Einstein, F.W.B.; Mario Pinto, B. Synthesis of sulfur analogues of methyl and allyl kojibiosides and methyl isomaltoside and conformational analysis of the kojibiosides. Tetrahedron: Asymm. 1994, 5, 2367-2396.
57. Hughes, N.A.; Munkombwe, N.M.; Todhunter, N.D. Synthesis of derivatives of 5-thio-L-idose. Carbohydr. Res. 1991, 216, 119-139.
58. López de la Paz, M.; Ellis, G.; Pérez, M.; Perkins, J.; Jiménez-Barbero, J.; Vicent, C. Carbohydrate hydrogen-bonding cooperativity - intramolecular hydrogen bonds and their cooperative effect on intermolecular processes - binding to a hydrogen-bond acceptor molecule. Eur. J. Org. Chem. 2002, 840-855.
59. Longchambon, F.; Ohannessian, J.; Avenel, D.; Neuman, A. Structure cristalline du β-D-galactose et de 1′α-L-Fucose. Acta Cryst. 1975, 31, 2623-2627.
60. Cramer, C.J.; Truhlar, D.G.; French, A.D. Exo-anomeric effects on energies and geometries of different conformations of glucose and related systems in the gas phase and aqueous solution. Carbohydr. Res. 1997, 298, 1-14.
61. Izumi, K. NMR spectra of some monosaccharides of galactopyranose series in deuterium oxide. Agr. Biol. Chem. 1971, 35, 1816-1818.
62. Lambert, J.B.; Wharry, S.M. Conformational analysis of 5-thio-D-glucose. J. Org. Chem. 1981, 46, 3193-3196.