Examples of results are given for 11 a-linked disaccharide methyl glycoside derivatives. This graphical application works with a Newman projection of the molecular fragment and displays a plot of J values versus the torsion angle. Karplus equations of varying complexity are available for most of the three- and four-bond spin—spin coupling constants that are commonly measured for carbohy- drates.
Similar equations have also been developed for one- and two-bond couplings between pairs of nuclei that are not directly connected by a dihedral angle, but instead depend on the relative torsion angles of substituents either inside, or outside the coupling pathway. The coefficients in the equations have in most cases been deter- mined by fitting of experimental data and are specific for particular pairs of nuclei separated by various coupling pathways.
These coefficients are summarized in Table I. The main text or original publications should be consulted for full details. Many of the three-parameter equations have been constructed from quite small experimental data sets, especially for the heteronuclear couplings. A notable exception is the work of Serianni and coworkers, who have generated vast quantities of coupling-constant data, experimentally from 13 C-substituted sugars, and theoretically by DFT methods.
The inclusion, in the Karplus equation, of other admittedly important molecular properties such as atomic or group electronegativity, electronegativity orientation, valence-bond angle, and bond length requires large experimental or theoretical data sets and has not been performed for all combinations of nuclei, and of coupling pathway. As the quantity of available experimental and theoretical data has increased, there has been a trend towards parametrization of multiple Karplus equations for various structural elements, especially for different coupling pathways, and anomeric configurations.
As an alternative to the use of these empirically derived equations, Serianni et al. Interactive, online programs are available for the calculation of coupling constants, dihedral angles, and the 1H—1H distance across thr a-linkages of some disaccharides, as well as a program for plotting up to five Karplus curves.
Karplus, Contact electron—spin coupling of nuclear magnetic moments, J. Lemieux, R.
Kullnig, H. Bernstein, and W. Schneider, Configurational effects on the proton magnetic resonance spectra of six-membered ring compounds, J. Kullnig, and R. Moir, The configuration of the 3-methoxycyclohexene oxides. A novel application of proton magnetic resonance spectroscopy to the determination of structure and configuration, J.
Dalton, Karplus equation. Theoretical calculation links NMR coupling constant to molecular geometry, Chem. News, 81 37— Lenz and J. Heeschen, The application of nuclear magnetic resonance to structural studies of carbohydrates in aqueous solution, J. Polymer Sci. Abraham, L. Hall, L. Hough, and K. McLauchlan, A proton resonance study of the conformations of carbohydrates in solution. Part I. Derivatives of 1,2-O-isopropylidene-a-D-xylo- hexofuranose, J. Hall, Nuclear magnetic resonance, Adv. Karplus, Vicinal proton coupling in nuclear magnetic resonance, J. Taravel, Carbon—proton coupling constants in the conformational analysis of sugar molecules, Adv.
Perlin and B. Bock, I. Lundt, and C. Pedersen, Assignment of anomeric structure to carbohydrates through geminal 13C-H coupling constants, Tetrahedron Lett. Bock and C. Pedersen, A study of 13CH coupling constants in hexopyranoses, J. Perkin II — Pedersen, A study of 13CH coupling constants in pentopyranoses and some of their derivatives, Acta Chem. Pedersen, Determination of one-bond carbon—proton coupling constants through 13 C-satellites in 1H-n.
Hricovini and I. Taravel, One-bond carbon—proton coupling constants: Angular dependence in a-linked oligosaccharides, Carbohydr. Taravel, One-bond carbon—proton coupling constants: Angular dependence in b-linked oligosaccharides, J. NMR, 2 — Ernst, Sensitivity enhancement in magnetic resonance, Advan.
Ernst and W. Anderson, Application of Fourier transform spectroscopy to magnetic resonance, Rev. Coxon, Conformational analysis via nuclear magnetic resonance spectroscopy, Methods Carbohydr. Brinkmann, H. Luthman, L. Eriksson, and M. Levitt, Determination of molecular geometry by high-order multiple-quantum evolution in solid-state NMR, J. Karplus, Theory of proton coupling constants in unsaturated molecules, J.
Abraham and K. Pachler, The proton magnetic resonance spectra of some substituted ethanes. Durette and D. Horton, Conformational studies on pyranoid sugar derivatives by NMR spectros- copy. Correlations of observed proton—proton coupling constants with the generalized Karplus equation, Org. Streefkerk, M. De Bie, and J. Vliegenthart, Conformational studies on pertrimethyl- silyl derivatives of some mono- and disaccharides by MHz PMR spectroscopy, Tetrahedron, 29 — Vliegenthart, Conformational studies of pertrimethyl- silyl derivatives of some 6-deoxyaldohexopyranoses and four less-common aldohexopyranoses by MHz P.
Substituent and configurational effects on the chemical shifts of the ring protons, Carbohydr. Dorland, B. Schut, J. Vliegenthart, G. Strecker, B. Fournet, G. Spik, and J. Montreuil, Structural studies on 2-acetamidoN- 4-L-aspartyl deoxy-b-D-glucopyranosylamine and 2-acetamidoO- a-L-fucopyranosyl N- 4-L-aspartyl deoxy-b-D-glucopyranosylamine, Eur. Williams and N. Bhacca, Dependency of vicinal coupling constants on the configuration of electronegative substituents, J.
Abraham and G. Gatti, Rotational isomerism. Part VII. B — Phillips and V. Wray, The structural dependence of the inductive effect. Part VI. The calculation of vicinal proton—proton spin—spin coupling constants in substituted ethanes, J. Haasnoot, F. Altona, Interpretation of vicinal proton—proton coupling constants by a generalized Karplus relation.
Conformational analysis of the exocyclic C —C bond in nucleosides and nucleotides, Recueil, J. Netherlands Chem. Altona, The relationship between proton—proton NMR coupling constants and substituent electronegativities-I. An empirical generalization of the Karplus equation, Tetrahedron, 36 — Altona, The relationship between proton—proton NMR coupling constants and substituent electronegativities. II-Conformational analy- sis of the sugar ring in nucleosides and nucleotides in solution using a generalized Karplus equation, Org.
The effect of substituents on vicinal couplings in monosubstituted ethanes, Tetrahedron, 27 — Pachler, The dependence of vicinal proton—proton coupling constants on dihedral angle and substituents, J.
Advances in Carbohydrate Chemistry and Biochemistry, Volume 59 - 1st Edition
Booth, The variation of vicinal proton—proton coupling constants with orientation of electronega- tive substituents, Tetrahedron Lett. Balacco, A desktop calculator for the Karplus equation, J. Cerda-Garcia-Rojas, L. Zepeda, and P.
Methods, 3 — Altona, Relationship between proton—proton NMR coupling constants and substituent electronegativities. Conformational anal- ysis of proline rings in solution using a generalized Karplus equation, Biopolymers, 20 — Altona and M. Sundaralingam, Conformational analysis of the sugar ring in nucleosides and nucleotides. A new description using the concept of pseudorotation, J. Improved method for the interpretation of proton magnetic resonance coupling constants, J. Abraham, P. Loftus, and W. Thomas, Rotational isomerism-XXI. Altona and C. Haasnoot, Prediction of anti and gauche vicinal proton—proton coupling constants in carbohydrates: A simple additivity rule for pyranose rings, Org.
Colucci, S. Jungk, and R. Gandour, An equation utilizing empirically derived substituent constants for the prediction of vicinal coupling constants in substituted ethanes, Magn. Huggins, Bond energies and polarities, J. Pauling, The nature of the chemical bond. The energy of single bonds and the relative electronegativity of atoms, J. Altona, J. Ippel, A. Westra Hoekzema, C. Erkelens, M. Groesbeek, and L. Donders, Relationship between proton—proton NMR coupling constants and substituent electronegativities.
Empirical substituent constants derived from ethanes and propanes, Magn. Donders, F. Altona, Through-space effects on vicinal proton spin—spin coupling constants mediated via hetero atoms: Nonequivalence of cis-couplings in five- membered rings, J. Marchand, N. Marchand, and A. Segre, NMR studies of rigid bicyclic systems. Evidence for the nonequivalence of exo—exo and endo—endo coupling constants in 7-substituted-1,4- dichloro-2,2,3,3-tetradeuterionorbornanes, Tetrahedron Lett.
Marshall, S. Walter, M. Barfield, A. Segre, Reasons for the nonequivalence of the exo—exo and endo—endo vicinal NMR coupling constants in norbor- nanes, Tetrahedron, 32 — Kessler, A. Friedrich, and W. Hull, Peptide conformation. Conformation of cyclo- L-Pro3 in solution, J. Kessler, W. Bermel, A. Friedrich, G. Krack, and W. Imai and E. Altona, R. Francke, R. Ippel, G. Daalmans, A. Westra Hoekzema, and J.
Guilleme, C. Altona, and L. Donders, Vicinal proton—proton coupling constants. Formulation of an equation including interactions between substituents, Molec. Guilleme, J. Bermejo, and A. Esteban, Vicinal proton—proton coupling constants. II: Analysis of the effect of interaction between geminal substituents upon vicinal couplings to methyl groups, Molec.
Casanueva, and E. Stenutz, I. Carmichael, G. Widmalm, and A. Tafazzoli and M. Barfield and M. Karplus, Valence-bond bond-order formulation for contact nuclear spin—spin coupling, J. Coxon, Conformations and proton coupling constants in some methyl 4,6-O-benzylidene-a-D- hexopyranosides, Tetrahedron, 21 — Coxon, Deuterium isotope effects in carbohydrates revisited.
Bystrov, V. Ivanov, S. Portnova, T. Balashova, and Y. Ovchinnikov, Refinement of the angular dependence of the peptide vicinal NH-C alpha H coupling constant, Tetrahedron, 29 — Almond, A. Brass, and J. Sheehan, Dynamic exchange between stabilized conformations predicted for hyaluronan tetrasaccharides: Comparison of molecular dynamics simulations with available NMR data, Glycobiology, 8 — Mobli and A.
Fraser, M. Kaufman, P. Morand, and G. Poppe and H. Evidence for a strong intramolecular hydrogen bond in sialic acid residues, J. Coxon, Boat conformations: Synthesis, NMR spectroscopy, and molecular modeling of methyl 2,6- anhydrodeoxyphthalimido-a-D-mannopyranoside and its 15N-labeled analog, Carbohydr. Zhao, Q. Pan, W. Zhang, I. Carmichael, and A. Carleer and M. Anteunis, Angular dependence of the vicinal interproton spin—spin coupling in silacyclohexanes. The conformational energy term of the methyl group in 1-methylsilacyclohexane, Org.
Lemieux, T. Nagabhushan, and B. Paul, Relationship of 13C to vicinal 1H coupling to the torsion angle in uridine and related structures, Can. Hamer, F. Balza, N. Cyr, and A. Coxon, Carbon Nuclear magnetic resonance spectroscopy of food-related disaccharides and trisaccharides, In Developments in Food Carbohydrate-2, C. Lee, Ed. Mulloy, T. Frenkiel, and D. Davies, Long-range carbon—proton coupling constants. Applica- tion of conformational studies of oligosaccharides, Carbohydr. Cloran, I. Pozsgay, N. Sari, and B. Widmalm, Conformational flexibility of the disaccharide a-D-Manp- 1!
Nishida, G. Widmalm, and P. Sandor, Hadamard long-range proton—carbon coupling constant measurements with band-selective proton decoupling, Magn. Kjellberg, C. Damberg, T. Nishida, and G. Widmalm, Magn. Cheetham, P. Dasgupta, and G. Ball, NMR and modelling studies of disaccharide conformation, Carbohydr. Houseknecht, T. Lowary, and C.
Hadad, Improved Karplus equations for 3JC1,H4 in aldopentofuranosides: Application to the conformational preferences of the methyl aldopentofurano- sides, J. B, 31 — Aydin and H. Koch and A. Bond-polarization differences between the anomers of D-glucose, Carbohydr. Taravel, V. Durier, C. Gouvion, K. Mazeau, and I.
Mazeau, M. Blanc-Muesser, S. Lavaitte, H. Driguez, and F. Taravel, Karplus-type equation for vicinal carbon—proton coupling constants for the C—S—C—H pathway in 1-thioglycosides, Carbohydr. Carmichael, D. Chipman, C. Podlasek, and A. Serianni, Torsional effects on the one-bond 13 C—13C spin coupling constant in ethylene glycol: Insights into the behavior of 1JCC in carbohydrates, J.
Batta and K. Williamson, B. Gerwick, and K. Gerwick, and R. Batta, and K. Coxon and R. Reynolds, Synthesis of nitrogenlabeled amino sugar derivatives by addition of phthalimideN to a carbohydrate epoxide, Carbohydr. Reynolds, Boat conformations. Synthesis, NMR spectroscopy, and molecular dynamics of methyl 4,6-O-benzylidenedeoxyphthalimido-a-D-altropyranoside derivatives, Carbohydr. Coxon, unpublished. Bystrov, Y.
Gavrilov, and V. Comparison of experimental and theoretical data, J. Lankhorst, C. Haasnoot, C. Erkelens, and C. Altona, Carbon NMR in conformational analysis of nucleic acid fragments. Erkelens, H. Westerink, G. Zimmer, J. Marino, and C. Mooren, S. Wijmenga, G. Plavec and J. Duker and A. Serianni, 13C -Substituted sucrose: 13C—1H and 13C—13C spin coupling constants to assess furanose ring and glycosidic bond conformations in aqueous solution, Carbohydr.
Zhao, G. Bondo, J. Zajicek, and A. Serianni, Two-bond 13C—13C spin-coupling constants in carbohydrates: New measurements of coupling signs, Carbohydr. Church, I. Serianni, Two-bond 13C—13C spin coupling constants in carbohy- drates: Effect of structure on coupling magnitude and sign, Carbohydr.
Serianni, P. Bondo, and J. Zajicek, Verification of the projection resultant method for two- bond 13C—13C coupling sign determinations in carbohydrates, J. Xu and C. Bush, Measurement of long-range carbon—carbon coupling constants in a uniformly enriched complex polysaccharide, Carbohydr. Bush, Molecular modeling of the flexible cell wall polysaccharide of Streptococcus mitis J22 on the basis of heteronuclear NMR coupling constants, Biochemistry, 35 — Bax, D. Max, and D. King-Morris and A. Wu, P.
Bondo, T. Vuorinen, and A. Serianni, 13C—13C Spin coupling constants in aldoses enriched with 13C at the terminal hydroxymethyl carbon: Effect of coupling pathway structure on JCC in carbohydrates, J. Milton, R. Harris, M. Probert, R. Field, and S. Homans, New conformational constraints in isotopically 13C enriched oligosaccharides, Glycobiology, 8 — Bose, S.
Zhao, R. Stenutz, F. Cloran, P. Bondo, G. Bondo, B. Hertz, I. Conn, and M. Barfield, Vicinal 13C—13C spin-spin coupling constants of 1-butanols, Org. Marshall,, Carbon—carbon and carbon—proton NMR couplings. Applications to organic stereo- chemistry and conformational analysis, Methods in Stereochemical Analysis Vol. Zhao, I. Doddrell, I. Burfitt, J. Grutzner, and M.
Barfield, Experimental and theoretical studies of vicinal 13 C—13C coupling oonstants, J. Barfield, I. Burfitt, and D. Doddrell, Conformational and substituent dependencies of 13C—13C coupling constants, J. Barfield, S. Conn, J. Marshall, and D. Miiller, Experimental and theoretical studies of the conformational and substituent dependencies of vicinal 13C—13C coupling constants. Impinging multiple rear-lobe effects, J. Barfield, J. Marshall, E. Canada, and M. Marshall, L. Faehl, and R. Berger, The conformational dependence of vicinal 13C13C spin—spin coupling constants in alicyclic compounds, Org.
Denisov, A. Tkachev, and V. Mamatyuk, Vicinal 13C—13C coupling constants in bicyclic monoterpenes, Magn. Thibaudeau, R. Stenutz, B. Hertz, T. Klepach, S. Wu, I. Hall and D. Jones, Observations on the electronegativity dependence of vicinal 19F-1H coupling constants, Can. Hamman, C. Charlon, and C. Influence of electronegativity on vicinal proton— proton and fluorine—proton coupling constants, Org. Thibaudeau, J. Plavec, and J. Chattopadhyaya, A new generalized Karplus-type equation relating vicinal proton—fluorine coupling constants to H—C—C—F torsion angles, J.
Hammer and S. B, 29 — Michalik, M. Hein, and M. Deitz, Color and Turbidity of Sugar Products, Karabinos and M. Hindert, Carboxymethylcellulose, Ellis and J. Honeyman, Glycosylamines, Hodge, The Amadori Rearrangement, Haynes and F. Polglase, Polysaccharides Associated with Wood Celloluse, Foster and A. Huggard, The Chemsitry of Heparin, Bobbitt, Periodate Oxidation of Carbohydrates, Bayne and J. Fewster, The Osones, Beelik, Kojic Acid, Hough and J.
Jones, The Biosynthesis of the Monosaccharides, Shafizadeh, Branched-chain Sugars of Natural Occurrence, Barker, The Nucleic Acids, Greenwood, Aspects of the Physical Chemistry of Starch, Neeley, Infrared Spectra of Carbohydrates, Sowden, The Saccharinic Acids, Foster, Zone Electrophoresis of Carbohydrates, Honeyman and J.
Morgan, Sugar Nitrates, McCloskey, Benzyl Ethers of Sugars, Conchie, G. Levvy and C. French, The Schardinger Dextrins, Manners, The Molecular Structure of Glycogens, Whistler and E. Olson, The Biosynthesis of Hyaluronic Acid, Speck Jr. Crum, The Four-carbon Saccharinic Acids, Goodman, Glycosyl Ureides, Zilliken and M. Stoloff, Polysaccharide Hydrocolloids of Commerce, Whistler and J. BeMiller, Alkaline Degredation of Polysaccharides, Caesar, Starch Nitrate, Perlin, Action of Lead Tetraacetate on the Sugars, Ellis, The Maillard Reaction, Angyal and L.
Anderson, The Cyclitols, Foster and D. Horton, Aspects of the Chemistry of the Amino Sugars, Fox and I. Wempen, Pyrimidine Nucleosides, Marsh, Preparation and Properties of -Glucuronidase, Aspinall, Structural Chemistry of the Hemicelluloses, Capon and W. Overend, Constitution and Physiochemical Properties of Carbohydrates, Bouveng and B. Lindberg, Methods in Structural Polysaccharide Chemistry, Hough, J. Priddle and R. Theobald, The Carbonates and Thiocarbonates of Carbohydrates, Jonsen and S. Laland, Bacterial Nucleosides and Nucleotides, Davies, Polysaccharides of Gram-negative Bacteria, Neeley, Dextran: Structure and Synthesis, Foster and J.
Webber, Chitin, Phillips, Radiation Chemistry of Carbohydrates, Micheel and A. Klemer, Glycosyl Fluorides and Azides, Clamp L. Hickson, and R. Whistler, Lactose, Lederer, Glycolipids of Acid-fast Bacteria, Wallenfels and O. Malhotra, Galactosidases, Muetgeert, The Fractionation of Starch, Mehta, P.
Dubach and H. Deuel, Carbohydrates in the Soil, Webber, Higher-carbon Sugars, Reichstein and E. Weiss, The Sugars of Cardiac Glycosides, Bailey and J. Pridham, Oligosaccharides, Heyns and H. Theander, Dicarbonyl Carbohydrates, Montgomery and H. Thomas, Purine Nucleosides, Phillips, Photochemistry of Carbohydrates, Weigel, Paper Electrophoresis of Carbohydrates, ElKhadem, Chemistry of Osotriazoles, Horton and D.
Hutson, Developments in the Chemistry of Thio Sugars, Birch, Trehaloses, Neufeld and W. Banks and C. Greenwood, Physical Properties of Solutions of Polysaccharides, Jeffrey and R. Rosenstein, Crystal-structure Analysis in Carbohydrate Chemistry, Spedding, Infrared Spectroscopy and Carbohydrate Chemistry, Hall, Nuclear Magnetic Resonance, Anet, 3-Deoxyglycosuloses 3-deoxyglycosones and the Degredation of Carbohydrates, Jones, Structure and Some Reactions of Cellulose, Timell, Wood Hemicelluloses: Part I. How , J. Brimacombe and M.
Stacey, The Pneumococcal Polysaccharides, Ferrier, Unsaturated Sugars, ElKhadem, Chemistry of Osazones, Turvey, Sulfates of the Simple Sugars, Kochetkov and O. Chizov, Mass Spectrometry of Carbohydrate Derivatives, Green, The Glycofuranosides, Hanessian, Deoxy Sugars, Rendleman Jr. Zorbach and K. Bhat, Synthetic Cardenolides, Archibald and J. Baddiley, The Teichoic Acids, Goldstein and T. Hullar, Chemical Synthesis of Polysaccharides, Guthrie and J. McCarthy, Acetolysis, Goodman, Neighboring-group Participation in Sugars, Barnett, Halogenated Carbohydrates, Verstraeten, D-Fructose and Its Derivatives, Ueda and J.
Fox, The Mononucleotides, Marchessault and A. Sarko, X-Ray Structure of Polysaccharides, Greenwood, The Thermal Degredation of Starch, Pigman and H. Paulsen and K. Ball and F. Greenwood and E. Gorin and J. Spencer, Structural Chemistry of Fungal Polysaccharides, Shafizadeh, Pyrolysis and Combustion of Cellulosic Materials, Baer, The Nitro Sugars, Parrish, Sulfonic Esters of Carbohydrates. Part II, Aspinall, Gums and Mucilages, Kiss, Glycosphingolipids Sugar-Sphingosine Conjugates , Churms, Gel Chromatography of Carbohydrates, Williams, Oxirane Derivatives of Aldoses, Defaye, 2, 5 Anhydrides of Sugars and Related Compounds, Soltzberg, Alditol Anhydrides, Siddiqui, The Sugars of Honey, Marshall and A.
Neuberger, Aspects of the Structure and Metabolism of Glycoproteins, Durette and D. Brady Jr. Butterworth and S. Shafizadeh and G. Nikaido and W. Moye, Non-aqueous Solvents for Carbohydrates, Barnett and D. Zhdanov, Y. Authors whose native language is not English are strongly encouraged to have their manuscripts proofread prior to submission. Authors must declare any financial support or relationships that may pose a conflict of interest.
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Genetic diversity analysis of South and East Asian duck populations using highly polymorphic microsatellite markers. Asian-Australas J Anim Sci ; Variation in myogenic differentiation 1 mRNA abundance is associated with beef tenderness in Nelore cattle. Anim Genet Mar 30 [Epub]. An upper limit for caloric density of finishing diets.
J Anim Sci ;84 Suppl:E Improved postweaning pig performance by adding NaCl or HCl to diets containing animal plasma [abstract]. J Anim Sci ;74 Suppl 1 Scientific farm animal production: an introduction to animal science. Nutrient requirements of swine. The human environment interface: applying ecosystem concepts to health. One health: the human-animal-environment interfaces in emerging infectious diseases. New York: Springer-Verlag; Web sites Raosoft.
Chemical studies of dissolved carbohydrates in seawater
Sample size calculator [Internet]. Raosoft Inc. Dissertations and Theses Ha JK.