Two-bond 13C-13C spin-coupling constants in carbohydrates: Effect of structure on coupling magnitude and sign

Carbohydrate Research

Volumn 280, Issue 2, 1996, Pages 177-186

  Church, Timothy ^a   Carmichael, Ian ^b   Serianni, Anthony S ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

Conformational analysis; Coupling constants, two bond 13C 13C spin spin

Indexed keywords

MONOSACCHARIDE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; THEORY;

EID: 0030058697     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/0008-6215(95)00311-8     Document Type: Article

References (32)

1. A.D. French and J. Brady (Eds.), Computer Modeling of Carbohydrate Molecules, ACS Symp. Ser., 430 (1990).
2. O. Jardetzky, Biochim. Biophys. Acta, 621 (1980) 227-232.
3. P.C. Kline and A.S. Serianni, J. Am. Chem. Soc., 112 (1990) 7373-7381.
4. A.S. Serianni, in C.I. Stassinopoulou (Ed.), NMR of Biological Macromolecules, NATO ASI Series H; Cell Biology, Vol. 87, Springer, Berlin, 1994, pp 293-306.
5. J.R. Snyder and A.S. Serianni, J. Org. Chem., 51 (1986) 2694-2702.
6. A.S. Serianni and C.A. Podlasek, Carbohydr. Res., 259 (1994) 277-282.
7. C.A. Podlasek, J. Wu, W.A. Stripe, P.B. Bondo, and A.S. Serianni, J. Am. Chem. Soc., 117 (1995) 8635-8644.
8. A.S. Serianni, J. Wu, and I. Carmichael, J. Am. Chem. Soc., 117 (1995) 8645-8650.
9. M.J. King-Morris and A.S. Serianni, J. Am. Chem. Soc., 109 (1987) 3501-3508.
10. J. Wu, P.B. Bondo, T. Vuorinen, and A.S. Serianni, J. Am. Chem. Soc., 114 (1992) 3499-3505.
11. A.S. Serianni and R. Barker, J. Org. Chem., 49 (1984) 3292-3300.
12. I. Carmichael, D.M. Chipman, C.A. Podlasek, and A.S. Serianni, J. Am. Chem. Soc., 115 (1993) 10863-10870.
13. P.C. Kline and A.S. Serianni, J. Org. Chem., 57 (1992) 1772-1777.
14. T. Bandyopadhyay, J. Wu, and A.S. Serianni, J. Org. Chem., 58 (1993) 5513-5517.
15. J.A. Schwarcz, N. Cyr, and A.S. Perlin, Can. J. Chem., 50 (1972) 3667-3676.
16. I. Tvaroska, M. Hricovini, and E. Petrakova, Carbohydr. Res., 189 (1989) 359-362.
17. J.A. Schwarcz, N. Cyr, and A.S. Perlin, Can. J. Chem. 53 (1975) 1872-1875.
18. K. Bock and C. Pedersen, Acta Chem. Scand., Ser. B, 31 (1977) 354-358.
19. T.E. Walker, R.E. London, T.W. Whaley, R. Barker, and N.A. Matwiyoff, J. Am. Chem. Soc., 98 (1976) 5807-5813.
20. R. Barker and T.E. Walker, Methods Carbohydr. Chem., 8 (1980) 151-165.
21. P.E. Hansen, Org. Magn. Reson., 11 (1978) 215-233.
22. S.J. Angyal, Angew. Chem., Intl. Ed. Engl., 8 (1969) 157-226.
23. S.J. Angyal, Adv. Carbohydr. Chem. Biochem., 42 (1984) 15-68.
24. M.J. Frisch, G.W. Trucks, M. Head-Gordon, P.M.W. Gill, M.W. Wong, J.B. Foresman, B.G. Johnson, H.B. Schlegel, M.A. Robb, E.S. Replogle, R. Gomperts, J.L. Andres, K. Raghavachari, J.S. Binkley, C. Gonzales, R.L. Martin, D.J. Fox, D.J. DeFrees, J. Baker, J.J.P Stewart, and J.A. Pople, Gaussian 92, Revision C.3; Gaussian, Inc., Pittsburgh, PA, 1992.
25. I. Carmichael, J. Phys. Chem., 97 (1993) 1789-1792.
26. J.L. Marshall, Carbon-Carbon and Carbon-Proton NMR Couplings: Applications to Organic Stereochemistry and Conformational Analysis, Verlag Chemie International, Deerfield Beach, FL, 1983, p 207.
27. H.A. Nunez and R. Barker, Biochemistry, 19 (1980) 489-495.
28. P.R. Rosevear, H.A. Nunez, and R. Barker, Biochemistry, 21 (1982) 1421-1431.
29. M.L. Hayes, A.S. Serianni, and R. Barker, Carbohydr. Res., 100 (1982) 87-101.
30. J.M. Duker and A.S. Serianni, Carbohydr. Res., 249 (1993) 281-303.
31. R.U. Lemieux, Pure Appl. Chem., 25 (1971) 527-548.
32. R.U. Lemieux, S. Koto, and D. Voisin, ACS Symp. Ser., 87 (1979) 17-29.