Complete 1H and 13C NMR chemical shift assignments of mono- to tetrasaccharides as basis for NMR chemical shift predictions of oligosaccharides using the computer program CASPER

Carbohydrate Research

Volumn 380, Issue , 2013, Pages 156-166

  Rönnols, Jerk ^a   Pendrill, Robert ^a   Fontana, Carolina ^a   Hamark, Christoffer ^a   D'Ortoli, Thibault Angles ^a   Engström, Olof ^a   Ståhle, Jonas ^a   Zaccheus, Mona V ^a   Säwén, Elin ^a   Hahn, Liljan E ^a   Iqbal, Shahzad ^a   Widmalm, Göran ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Automation; Chemical shift prediction; Glycan; Oligosaccharide

Indexed keywords

AUTOMATION; FORECASTING; FUNCTIONAL GROUPS; GLUCOSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOSACCHARIDES; POLYSACCHARIDES;

ANOMERIC FORMS; GLYCAN; HEPTASACCHARIDES; LINE-SHAPE ANALYSIS; NMR CHEMICAL SHIFTS; PENTASACCHARIDES; STRUCTURAL DETERMINATION; TETRASACCHARIDES;

CHEMICAL SHIFT;

DISACCHARIDE; FUCOSE; MANNOSE; MONOSACCHARIDE; OLIGOSACCHARIDE; PENTASACCHARIDE; TETRASACCHARIDE; TRISACCHARIDE;

ACCURACY; ARTICLE; CARBOHYDRATE ANALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; COMPUTER PROGRAM; GLYCOSYLATION; NONHUMAN; PREDICTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE;

AUTOMATION; CHEMICAL SHIFT PREDICTION; GLYCAN; OLIGOSACCHARIDE;

MAGNETIC RESONANCE SPECTROSCOPY; MONOSACCHARIDES; OLIGOSACCHARIDES; SOFTWARE;

EID: 84883737726     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2013.06.026     Document Type: Article

References (73)

1. S. Herget, P.V. Toukach, R. Ranzinger, W.E. Hull, Y.A. Knirel, and C.W. von der Lieth BMC Struct. Biol. 8 2008 35
2. V. Bouvet, and R.N. Ben Cell Biochem. Biophys. 39 2003 133 144
3. M.L. Rosén Klement, L. Öjemyr, K. Tagscherer, G. Widmalm, and Å. Wieslander Mol. Microbiol. 65 2007 1444 1457
4. H. Pfander, and H. Stoll Nat. Prod. Rep. 8 1991 69 95
5. G. Widmalm Carbohydr. Res. 378 2013 123 132
6. S. Krapp, Y. Mimura, R. Jefferis, R. Huber, and P. Sondermann J. Mol. Biol. 325 2003 979 989
7. S. Daikoku, G. Widmalm, and O. Kanie Rapid Commun. Mass Spectrom. 23 2009 3713 3719
8. H. Li, B. Bendiak, W.F. Siems, D.R. Gang, and H.H. Hill Jr. Anal. Chem. 85 2013 2760 2769
9. J.H. Prestegard, S.C. Sahu, W.K. Nkari, L.C. Morris, D. Live, and C. Gruta J. Biomol. NMR 55 2013 201 209
10. S.L. Lam, K.F. Lai, and L.M. Chi J. Magn. Reson. 187 2007 105 111
11. D.S.M. Bot, P. Cleij, H.A. van't Klooster, H. van Halbeek, G.A. Veldink, and J.F.G. Vliegenthart J. Chemometr. 2 1988 11 27
12. F. Pereira Molecules 17 2012 3818 3833
13. F.V. Toukach, and A.S. Shashkov Carbohydr. Res. 335 2001 101 114
14. P.-E. Jansson, R. Stenutz, and G. Widmalm Carbohydr. Res. 341 2006 1003 1010
15. M. Lundborg, C. Fontana, and G. Widmalm Biomacromolecules 12 2011 3851 3855
16. P. Söderman, P.-E. Jansson, and G. Widmalm J. Chem. Soc., Perkin Trans. 2 1998 639 648
17. M. Lundborg, and G. Widmalm Anal. Chem. 83 2011 1514 1517
18. A.S. Shashkov, G.M. Lipkind, Y.A. Knirel, and N.K. Kochetkov Magn. Reson. Chem. 26 1988 735 747
19. A. Adeyeye, P.-E. Jansson, L. Kenne, and G. Widmalm J. Chem. Soc., Perkin Trans. 2 1991 963 973
20. M.U. Roslund, E. Säwén, J. Landström, J. Rönnols, K.H.M. Jonsson, M. Lundborg, M.V. Svensson, and G. Widmalm Carbohydr. Res. 346 2011 1311 1319
21. R.C. Beier, and B.P. Mundy J. Carbohydr. Chem. 3 1984 253 266
22. J. StanÄk Jr., J. Moravcová, and J. Jarý J. Carbohydr. Chem. 4 1985 79 90
23. B.M. Sattelle, S.U. Hansen, J. Gardiner, and A. Almond J. Am. Chem. Soc. 132 2010 13132 13134
24. W. Zhang, X. Hu, I. Carmichael, and A.S. Serianni J. Org. Chem. 77 2012 9521 9534
25. J. Gervay, and G. Batta Tetrahedron Lett. 35 1994 3009 3012
26. T. Klepach, W. Zhang, I. Carmichael, and A.S. Serianni J. Org. Chem. 73 2008 4376 4387
27. K. Bock, J. Defaye, H. Driguez, and E. Bar-Guilloux Eur. J. Biochem. 131 1983 595 600
28. K. Bock, and R.U. Lemieux Carbohydr. Res. 100 1982 63 74
29. M.J. McConville, and M.A.J. Ferguson Biochem. J. 294 1993 305 324
30. P. Shi, M.C. Silva, H.-Y.L. Wang, B. Wu, N.G. Akhmedov, M. Li, P.J. Beuning, and G.A. O'Doherty ACS Med. Chem. Lett. 3 2012 1086 1090
31. P.-M. Åberg, L. Blomberg, H. Lönn, and T. Norberg Glycoconjugate J. 7 1990 201 205
32. N. Fusetani, D. Ejima, S. Matsunaga, K. Hashimoto, K. Itagaki, Y. Akagi, N. Taga, and K. Suzuki Experientia 43 1987 464 465
33. G.S. Besra, M.R. McNeil, K.-H. Khoo, A. Dell, H.R. Morris, and P.J. Brennan Biochemistry 32 1993 12705 12714
34. S.W. Hunter, R.C. Murphy, K. Clay, M.B. Goren, and P.J. Brennan J. Biol. Chem. 258 1983 10481 10487
35. M. Díez-Municio, M. Herrero, M.L. Jimeno, A. Olano, and F.J. Moreno J. Agric. Food. Chem. 60 2012 10564 10571
36. S. Dasgupta, and M. Nitz Carbohydr. Res. 345 2010 2282 2286
37. B. Lindberg, L. Rodén, and B.-G. Silvander Carbohydr. Res. 2 1966 413 417
38. C. Hermida, G. Corrales, F.J. Cañada, J.J. Aragón, and A. Fernández-Mayoralas Bioorg. Med. Chem. 15 2007 4836 4840
39. L. Liao, and F.-I. Auzanneau J. Org. Chem. 70 2005 6265 6273
40. L. Liao, and F.-I. Auzanneau Org. Lett. 5 2003 2607 2610
41. L. Liao, and F.-I. Auzanneau Carbohydr. Res. 341 2006 2426 2433
42. J.L. Hendel, A. Cheng, and F.-I. Auzanneau Carbohydr. Res. 343 2008 2914 2923
43. A. Asnani, and F.-I. Auzanneau Carbohydr. Res. 343 2008 1653 1664
44. B.S. Komarova, Y.E. Tsvetkov, Y.A. Knirel, U. Zähringer, G.B. Pier, and N.E. Nifantiev Tetrahedron Lett. 47 2006 3583 3587
45. J.O. Duus, N.E. Nifant'ev, A.S. Shashkov, E.A. Khatuntseva, and K. Bock Isr. J. Chem. 40 2000 223 239
46. D. Vasiliu, N. Razi, Y. Zhang, N. Jacobsen, K. Allin, X. Liu, J. Hoffmann, O. Bohorov, and O. Blixt Carbohydr. Res. 341 2006 1447 1457
47. O. Blixt, B.E. Collins, I.M. van den Nieuwenhof, P.R. Crocker, and J.C. Paulson J. Biol. Chem. 278 2003 31007 31019
48. O. Blixt, J. Brown, M.J. Schur, W. Wakarchuk, and J.C. Paulson J. Org. Chem. 66 2001 2442 2448
49. O. Blixt, D. Vasiliu, K. Allin, N. Jacobsen, D. Warnock, N. Razi, J.C. Paulson, S. Bernatchez, M. Gilbert, and W. Wakarchuk Carbohydr. Res. 340 2005 1963 1972
50. J.P. Kamerling, R. Schauer, A.K. Shukla, S. Stoll, H. van Halbeek, and J.F.G. Vliegenthart Eur. J. Biochem. 162 1982 601 607
51. T. Ali, A. Weintraub, and G. Widmalm Carbohydr. Res. 341 2006 1878 1883
52. P.-E. Jansson, L. Kenne, and E. Schweda J. Chem. Soc., Perkin Trans. 1 1987 338 377
53. C. Fontana, K. Ramström, A. Weintraub, and G. Widmalm Glycobiology 23 2013 354 362
54. M.U. Roslund, O. Aitio, J. Wärnå, H. Maaheimo, D.Y. Murzin, and R. Leino J. Am. Chem. Soc. 130 2008 8769 8772
55. K. Zangger, and H. Sterk J. Magn. Reson. 124 1997 486 489
56. J.A. Aguilar, M. Nilsson, and G.A. Morris Angew. Chem., Int. Ed. 50 2011 9716 9717
57. R. Laatikainen, M. Niemitz, U. Weber, J. Sundelin, T. Hassinen, and J. Vepsäläinen J. Magn. Reson., Ser A 120 1996 1 10
58. R. Laatikainen, M. Niemitz, W.J. Malaisse, M. Biesemans, and R. Willem Magn. Reson. Med. 36 1996 359 365
59. M.U. Roslund, P. Tähtinen, M. Niemitz, and R. Sjöholm Carbohydr. Res. 343 2008 101 112
60. T. Klepach, I. Carmichael, and A.S. Serianni J. Am. Chem. Soc. 130 2008 11892 11900
61. A.B. Yongye, J. Gonzalez-Outeriño, J. Glushka, V. Schultheis, and R.J. Woods Biochemistry 47 2008 12493 12514
62. Y. Kubota, H. Hori, R. Sawa, H. Seki, and J. Uzawa Magn. Reson. Chem. 50 2012 659 664
63. M. Nilsson, and T. Norberg J. Carbohydr. Chem. 9 1990 1 14
64. M. Nilsson, and T. Norberg J. Carbohydr. Chem. 8 1989 613 627
65. R. Šardzík, R. Sharma, S. Kaloo, J. Voglmeir, P.R. Crocker, and S.L. Flitsch Chem. Commun. 47 2011 5425 5427
66. H.M.I. Osborn Carbohydrates 2003 Academic Press Amsterdam
67. D.R. Bundle, and R.U. Lemieux Methods Carbohydr. Chem. 7 1976 79 86
68. L. Braunschweiler, and R.R. Ernst J. Magn. Reson. 53 1983 521 528
69. T. Parella, F. Sánchez-Ferrando, and A. Virgili J. Magn. Reson. 126 1997 274 277
70. B.O. Petersen, E. Vinogradov, W. Kay, P. Würtz, N.T. Nyberg, J.O. Duus, and O.W. Sørensen Carbohydr. Res. 341 2006 550 556
71. A. Bax, and M.F. Summers J. Am. Chem. Soc. 108 1986 2093 2094
72. R. Laatikainen J. Magn. Reson. 92 1991 1 9
73. T.D.W. Claridge, and I. Pérez-Victoria Org. Biomol. Chem. 1 2003 3632 3634