Determination of acid dissociation constants of anomers of amino sugars by 1H NMR spectroscopy

Carbohydrate Research

Volumn 298, Issue 3, 1997, Pages 163-172

  Blaskó, Andrei ^a   Bunton, Clifford A ^a   Bunel, Sergio ^b   Ibarra, Carmen ^b   Moraga, Exiquiel ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CHILE   (Chile)

Author keywords

Amino sugars; Dissociation constants; NMR

Indexed keywords

AMINOSUGAR; GALACTOSAMINE; GLUCOSAMINE; MANNOSAMINE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; CARBOHYDRATE ANALYSIS; DISSOCIATION CONSTANT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PKA; PRIORITY JOURNAL;

EID: 0031041565     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(96)00290-X     Document Type: Article

References (42)

1. B. Capon and W.G. Overend, Adv. Carbohydr. Chem., 15 (1960) 11-51.
2. A. Albert and E.P. Serjeant, The Determination of Ionization Constants, 3rd ed., Chapman and Hall, London, 1984.
3. P. Dais and A.S. Perlin, Carbohydr. Res., 136 (1985) 215-223; M. Jasea, A.S. Perlin, and P. Dais, Mag. Reson. Chem., 28 (1990) 283-289.
4. P. Dais and A.S. Perlin, Carbohydr. Res., 136 (1985) 215-223; M. Jasea, A.S. Perlin, and P. Dais, Mag. Reson. Chem., 28 (1990) 283-289.
5. M.A. Kabayama and D. Patterson, Can. J. Chem., 36 (1958) 568-573.
6. J.M. Harvey and M.J.R. Symons, J. Solution Chem., 7 (1978) 571-586.
7. F. Franks, Pure Appl. Chem., 59 (1987) 1189-1202; S. Bociek and F. Franks, J. Chem. Soc., Faraday Trans. 1, 75 (1979) 262-270.
8. F. Franks, Pure Appl. Chem., 59 (1987) 1189-1202; S. Bociek and F. Franks, J. Chem. Soc., Faraday Trans. 1, 75 (1979) 262-270.
9. J.M. Losand and L.B. Simpson, Rec. Trav. Chim., 73 (1954) 941-958; 75 (1956) 267-285.
10. J.M. Losand and L.B. Simpson, Rec. Trav. Chim., 73 (1954) 941-958; 75 (1956) 267-285.
11. S. Bunel, C. Ibarra, E. Moraga, V. Calvo, A. Blaskó, and C.A. Bunton, Carbohydr. Res., 239 (1992) 185-196; A. Blaskó, C.A. Bunton, S. Bunel, E. Moraga, C. Ibarra, and J. Parada, Bol. Soc. Chil. Quim., 40 (1995) 449-454.
12. S. Bunel, C. Ibarra, E. Moraga, V. Calvo, A. Blaskó, and C.A. Bunton, Carbohydr. Res., 239 (1992) 185-196; A. Blaskó, C.A. Bunton, S. Bunel, E. Moraga, C. Ibarra, and J. Parada, Bol. Soc. Chil. Quim., 40 (1995) 449-454.
13. S. Bunel, C. Ibarra, E. Moraga, A. Blaskó, and C.A. Bunton, Carbohydr. Res., 244 (1993) 1-14.
14. E. Moraga, S. Bunel, C. Ibarra, A. Blaskó, and C.A. Bunton, Carbohydr. Res., 268 (1995) 1-15; A. Blaskó, C.A. Bunton, E. Moraga, S. Bunel, and C. Ibarra, Carbohydr. Res., 278 (1995) 315-328.
15. E. Moraga, S. Bunel, C. Ibarra, A. Blaskó, and C.A. Bunton, Carbohydr. Res., 268 (1995) 1-15; A. Blaskó, C.A. Bunton, E. Moraga, S. Bunel, and C. Ibarra, Carbohydr. Res., 278 (1995) 315-328.
16. D.M. Whitfield, S. Stojkovski, and B. Sarkar, Cord. Chem. Rev., 122 (1993) 171-225; Kozlowski, P. Decock, I. Oliver, G., Micera, A. Pusino, and L.D. Petitt, Carbohydr. Res., 197 (1990) 109-117, and references therein.
17. D.M. Whitfield, S. Stojkovski, and B. Sarkar, Cord. Chem. Rev., 122 (1993) 171-225; Kozlowski, P. Decock, I. Oliver, G., Micera, A. Pusino, and L.D. Petitt, Carbohydr. Res., 197 (1990) 109-117, and references therein.
18. A. Neuberger and A.P. Fletcher, J. Chem. Soc., B (1969) 178-181.
19. J. Keeler, Chem. Soc. Rev., 19 (1990) 381-406.
20. D. Horton, J.S. Jewell, and K.D. Philips, J. Org. Chem., 31 (1966) 4022-4025.
21. G.E. Martin and A.S. Zektzer, Two-Dimensional NMR Methods for Establishing Connectivity, VCH, New York, 1988, pp 99-101.
22. T.H. Fife and T.C. Bruice, J. Phys. Chem., 65 (1961) 1079-1079.
23. P. Ballinger and F.A. Long, J. Am. Chem. Soc., 81 (1959) 1050-1053, 2347-2352.
24. D.C. Martin and J.A.V. Butler, J. Chem. Soc., (1939) 1366-1369.
25. E. Högfeldt and J. Bigeleisen, J. Am. Chem. Soc., 82 (1960) 15-20.
26. C.A. Bunton and V.J. Shiner, J. Am. Chem. Soc., 83 (1961) 42-47.
27. A. De Bruyn, M. Anteunis, and P. Kovác, Coll. Czech. Chem. Comm., 42 (1977) 3057-3068.
28. S.J. Berners-Price, T.A. Frenkiel, U. Frey, J.D. Ranford, and P.J. Sadler, J. Chem. Soc., Chem. Commun., (1992) 789-791.
29. C.L. Perrin, Pure Appl. Chem., 67 (1995) 719-728.
30. E.L. Martell and R.M. Smith, Critical Stability Constants, Vol. 3, Plenum, New York, 1977, p 274.
31. A. Albert and E.P. Serjeant, The Determination of Ionization Constants, 3rd ed., Chapman and Hall, London, 1984, p 143; C.A. Bunton and H. Chaimovich, J. Am. Chem. Soc., 88 (1966) 4082-4089.
32. A. Albert and E.P. Serjeant, The Determination of Ionization Constants, 3rd ed., Chapman and Hall, London, 1984, p 143; C.A. Bunton and H. Chaimovich, J. Am. Chem. Soc., 88 (1966) 4082-4089.
33. J.G. Batchelor, J. Chem. Soc., Perkin Trans. 2, (1976) 1585-1590; H. Booth and M.L. Jozefowicz, J. Chem. Soc., Perkin Trans. 2, (1976) 895-901.
34. J.G. Batchelor, J. Chem. Soc., Perkin Trans. 2, (1976) 1585-1590; H. Booth and M.L. Jozefowicz, J. Chem. Soc., Perkin Trans. 2, (1976) 895-901.
35. E.L. Eliel, Stereochemistry of Carbon Compounds, McGraw-Hill, New York, 1962, ch. 8.
36. A.J. Kirby, The Anomeric Effect and Related Stereo-electronic Effects at Oxygen, Springer, New York, 1983; J.-P. Praly and R.U. Lemieux, Can. J. Chem., 65 (1987) 213-223; E. Juaristi and G. Cuevas, Tetrahedron, 48 (1992) 5019-5085.
37. A.J. Kirby, The Anomeric Effect and Related Stereo-electronic Effects at Oxygen, Springer, New York, 1983; J.-P. Praly and R.U. Lemieux, Can. J. Chem., 65 (1987) 213-223; E. Juaristi and G. Cuevas, Tetrahedron, 48 (1992) 5019-5085.
38. A.J. Kirby, The Anomeric Effect and Related Stereo-electronic Effects at Oxygen, Springer, New York, 1983; J.-P. Praly and R.U. Lemieux, Can. J. Chem., 65 (1987) 213-223; E. Juaristi and G. Cuevas, Tetrahedron, 48 (1992) 5019-5085.
39. C.L. Perrin and K.B. Armstrong, J. Am. Chem. Soc., 115 (1993) 6825-6834.
40. Handbook of Chemistry and Physics, 52 ed., R.C. Weast, Chemical Rubber Co., Cleveland, 1971, p D-117.
41. R.W. Lenz and J.P. Heeschen, J. Polym. Sci., 51 (1961) 247-261.
42. P.D.E. Pretsch, T. Clerc, J. Seibl, and W. Simon, Tables of Spectral Data for Determination of Organic Compounds, 2nd ed., Springer-Verlag, New York, 1989, p H25.