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Original Articles

Quantum Mechanical Calculation of 13C NMR Chemical Shifts in a Series of Isomeric Fucobiosides with the Account for Conformational Equilibrium

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Pages 93-104 | Received 01 Jul 2011, Accepted 11 Oct 2011, Published online: 07 Feb 2012

REFERENCES

  • Berteau , O. and Mulloy , B. 2003 . Sulfated fucans, fresh perspectives: structures, functions, and biological properties of sulfated fucans and an overview of enzymes active toward this class of polysaccharide . Glycobiology , 13 : 29R – 40R .
  • Cumashi , A. , Ushakova , N. A. , Preobrazhenskaya , M. E. , D’Incecco , A. , Piccoli , A. , Totani , L. , Tinari , N. , Morozevich , G. E. , Berman , A. E. , Bilan , M. I. , Usov , A. I. , Ustyuzhanina , N. E. , Grachev , A. A. , Sanderson , C. J. , Kelly , M. , Rabinovich , G. A. , Iacobelli , S. and Nifantiev , N. E. 2007 . A comparative study of the anti-inflammatory, anticoagulant, antiangiogenic, and antiadhesive activities of nine different fucoidans from brown seaweeds . Glycobiology , 17 : 541 – 552 .
  • Croci , D. O. , Cumashi , A. , Ushakova , N. A. , Preobrazhenskaya , M. E. , Piccoli , A. , Totani , L. , Ustyuzhanina , N. E. , Bilan , M. I. , Usov , A. I. , Grachev , A. A. , Morozevich , G. E. , Berman , A. E. , Sanderson , C. J. , Kelly , M. , Di Gregorio , P. , Rossi , C. , Tinari , N. , Iacobelli , S. , Rabinovich , G. A. and Nifantiev , N. E. 2011 . Fucans, but not fucomannoglucuronans, determine the biological activities of sulfated polysaccharides from Laminaria saccharina brown seaweed . PLoS ONE , 6 ( 2 ) : e17283 doi: 10.1371/journal.pone.0017283
  • Gerbst , A. G. , Grachev , A. A. , Ustuzhanina , N. E. , Nifantiev , N. E. , Vyboichtchik , A. A. , Shashkov , A. S. and Usov , A. I. 2010 . Application of artificial neural networks for analysis of 13C NMR spectra of fucoidans . J. Carbohydr. Chem. , 29 : 92 – 102 .
  • Ustyuzhanina , N. E. , Krylov , V. B. , Grachev , A. A. and Nifantiev , N. E. 2006 . NMR and conformational studies of fucoidan fragments. VIII. Convergent synthesis of branched and linear oligosaccharides . Synthesis , 23 : 4017 – 4031 .
  • Ustyuzhanina , N. E. , Krylov , V. B. , Usov , A. I. and Nifantiev , N. E. 2009 . “ Synthesis of fucoidan fragments ” . In Progress in the synthesis of complex carbohydrate chains of plant and microbial polysaccharides, Research Signpost Edited by: Nifantiev , N. E. 131 – 154 .
  • “ DALTON, a molecular electronic structure program, Release 2.0 (2005) ” . see http://www.kjemi.uio.no/software/dalton/dalton.html
  • Jorgensen , W. L. , Chandrasekhar , J. , Madura , J. D. , Impey , R. W. and Klein , M. L. 1983 . Comparison of simple potential functions for simulating liquid water . J. Chem. Phys. , 79 : 926 – 935 .
  • Leimkuhler , B. and Skeel , R. 1994 . Symplectic numerical integrators in constrained Hamiltonian systems . J. Comp. Phys. , 112 : 117 – 125 .
  • Tvaroška , I. and Gajdoš , J. 1995 . Angular dependence of vicinal carbon-proton coupling constants for conformational studies of the hydroxymethyl group in carbohydrates . Carbohydr. Res. , 251 : 151 – 162 .
  • Swalina , C. W. , Zauhar , R. J. , DeGrazia , M. J. and Moyna , G. 2001 . Derivation of 13C chemical shift surfaces for the anomeric carbons of oligosaccharides and glycopeptides using ab initio methodology . J. Biomol. NMR , 21 : 49 – 61 .
  • Tafazzoli , M. and Ghiasi , M. 2007 . New Karplus equations for 2JHH, 3JHH, 2JCH, 3JCH, 3JCOCH, 3JCSCH and 3JCCCH in some aldohexopyranoside derivatives as determined using NMR spectroscopy and density functional theory calculations . Carbohydr. Res. , 342 : 2086 – 2096 .
  • Gerbst , A. G. , Ustuzhanina , N. E. , Grachev , A. A. , Zlotina , N. S. , Khatuntseva , E. A. , Tsvetkov , D. E. , Shashkov , A. S. , Usov , A. I. and Nifantiev , N. E. 2002 . Synthesis, NMR and conformational studies of fucoidan fragments 4: 4-mono- and 4,4′-disulfated (1→3)-α-L-fucobioside and 4-sulfated fucoside fragments . J. Carbohydr. Chem. , 21 : 313 – 324 .
  • Grachev , A. A. , Gerbst , A. G. , Ustyuzhanina , N. E. , Krylov , V. B. , Shashkov , A. S. , Usov , A. I. and Nifantiev , N. E. 2007 . Modeling of polysaccharides with oligosaccharides: how large should the model be? . Mend. Commun. , 17 : 57 – 62 .
  • Hehre , W. J. , Ditchfield , R. and Pople , J. A. 1972 . Self-consistent molecular orbital methods. XII. Further extensions of Gaussian-type basis sets for use in molecular orbital studies of organic molecules . J. Chem. Phys. , 56 : 2257 – 2261 .
  • Dunning , T. H. Jr. 1970 . Gaussian basis functions for use in molecular calculations. I. Contraction of (9s5p) atomic basis sets for the first-row atoms . J. Chem. Phys. , 53 : 2823 – 2833 .
  • Schafer , A. , Horn , H. and Ahlrichs , R. 1992 . Fully optimized contracted Gaussian basis sets for atoms Li to Kr . J. Chem. Phys. , 97 : 2571 – 2577 .
  • Grossberg , S. 1976 . Adaptive pattern classification and universal recoding: I. Parallel development and coding of neural feature detectors . Biol. Cybern. , 23 : 121 – 134 .
  • Grossberg , S. 1976 . Adaptive pattern classification and universal recoding: I. Feedback, expectation, olfaction, illusion . Biol. Cybern. , 23 : 187 – 202 .
  • Carpenter , G. A. and Grossberg , S. 1987 . A massively parallel architecture neural pattern recognition machine . Comput. Vision Graph. , 37 : 54 – 115 .
  • Mulloy , B. , Frenkiel , T. A. and Davies , D. B. 1988 . Long-range carbon-proton coupling constants: application to conformational studies of oligosaccharides . Carbohydr. Res. , 184 : 39 – 46 .
  • Gerbst , A. G. , Grachev , A. A. , Ustuzhanina , N. E. , Khatuntseva , E. A. , Tsvetkov , D. E. , Usov , A. I. , Shashkov , A. S. , Preobrazenskaya , M. E. , Ushakova , N. A. and Nifantiev , N. E. 2004 . Synthesis, NMR and conformational studies of Fucoidan fragments. VI. Fragments with α-(1→2)-linked fucobioside unit . Russ. J. Bioorg. Chem. , 30 : 137 – 147 .

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