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Conformational Analysis of Monosaccharides

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Carbohydrates

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Abstract

Molecules are dynamic assemblies of atoms chemically linked by single or multiple bonds. Hence, all atoms as well as groups of atoms are in perpetual motion, vibrating and rotating about chemical bonds. The deformation of chemical bonds due to vibration (stretching, wagging, etc.) of atoms is quantized and it is not the subject of conformational analysis. However, the rotation of atoms about the single bonds is the subject of conformational analysis.

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References

  1. Lowe, J. P., “Barriers to internal rotation about single bonds”, Progr. Phys. Org. Chem. (1968) 6, 1–80

    Article  CAS  Google Scholar 

  2. Lowe, J. P., “Barrier to internal rotation in ethane”, Science (1973) 179, 527–532

    Article  CAS  Google Scholar 

  3. Oelfke, W. C.; Gordy, W., “Millimeter-wave spectrum of hydrogen peroxide”, J. Chem. Phys. (1969) 51, 5336–5343

    Article  CAS  Google Scholar 

  4. Bair, R. A.; Goddard, III, W. A., “Ab initio studies of the structure of peroxides and peroxy radicals”, J. Am. C hem. Soc. (1982) 104, 2719–2724

    Article  CAS  Google Scholar 

  5. Pitzer, K. S., “Potential energies for rotations about single bonds”, Discuss. Fara- day Soc. (1951) 10, 66–73

    Article  Google Scholar 

  6. Weiss, S.; Leroi, G. E., “Direct observation of the infrared torsional spectrum of C 2 H 6 , CH 3 CD 3 , and C 2 D 6 ”, J. Chem. Phys. (1968) 48, 962–967

    Article  CAS  Google Scholar 

  7. Hirota, E.; Saito, S.; Endo, Y., “Barrier to internal rotation in ethane from the microvawe spectrum of CH 3 CHD 2 ”, J. Chem. Phys. (1979) 71, 1183–1187

    Article  CAS  Google Scholar 

  8. Fantoni, R.; van Helroort, K.; Knippers, W.; Reuss, J., “Direct observation of torsional levels in Raman spectra of C 2 H 6 ”, Chem. Phys. (1986) 110, 1–16

    Article  CAS  Google Scholar 

  9. Pitzer, R. M., “The barrier to internal rotation in ethane”, Acc. Chem. Res. (1983) 16, 207–210

    Article  CAS  Google Scholar 

  10. Sovers, O. J.; Kern, C. W.; Pitzer, R. M.; Karplus, M., “Bond-function analysis of rotational barriers: Ethane”, J. Chem. Phys. (1968) 49, 2592–2599

    Article  CAS  Google Scholar 

  11. Bader, R. F. W.; Cheeseman, J. R.; Laidig, K. E.; Wiberg, K. B.; Brenemann, C., “Origin of rotation and inversion barriers”, J. Am. Chem. Soc. (1990) 112, 6530– 6536

    Article  CAS  Google Scholar 

  12. Klyne, W.; Prelog, V., “Description of steric relationship across single bond”, Experientia (1960) 16, 521–523

    Article  CAS  Google Scholar 

  13. Horton, D.; Wander, J. D., “Conformations of acyclic derivatives of sugars”, Carbohydr. Res. (1969) 10, 279–288

    Article  CAS  Google Scholar 

  14. Azarnia, N.; Jeffrey, G. A.; Kim, H. S.; Park, Y. J., Joint ACS/CIC Conference Abstracts of Papers, CARB 26 (1970)

    Google Scholar 

  15. Berman, H. M.; Rosenstein, R. D., “The crystal structure of galactitol”, Acta Cryst. (1968) B24, 435–441

    Google Scholar 

  16. Berman, H. M.; Jeffrey, G. A.; Rosenstein, R. D., “The crystal structures of the [alpha] and [beta] forms of D-mannitol”, Acta Cryst. (1968) B24, 442–449

    Google Scholar 

  17. Kim, S. H.; Jeffrey, G. A.; Rosenstein, R. D., “The crystal structure of the K form of D-mannitol”, Acta Cryst. (1968) B24, 1449–1455

    Google Scholar 

  18. Hunter, F. D.; Rosenstein, R. D., “The crystal structure of D,L-arabinitol”, Acta Cryst. (1968) B24, 1652–1660

    Google Scholar 

  19. Staab, H. A., “Einführug in die theoretische organische Chemie”, Verlag Chemie, 1960, p.547

    Google Scholar 

  20. Pitzer, K. S., “Strain energies of cyclic hydrocarbons”, Science, (1945) 101, 672

    Article  CAS  Google Scholar 

  21. Kilpatrick, J. E.; Pitzer, K. S.; Spitzer, R., “The thermodynamics and molecular structure of cyclopentane”, J. Am. Chem. Soc. (1947) 69, 2483–2488

    Article  CAS  Google Scholar 

  22. Pitzer, K. S.; Donath, W. E., “Conformations and strain energy of cyclopentane and its derivatives”, J. Am. Chem. Soc. (1959) 81, 3213–3218

    Article  CAS  Google Scholar 

  23. Brutcher, F. V., Jr.; Roberts, T.; Barr, S. J.; Pearson, N., “The conformations of substituted cyclopentanes. I. The infrared analysis and structure of the α -Halocam phors, the α -Halo-2-indanones and the α -Halocyclopentanones”, J. Am. Chem. Soc. (1959) 81, 4915–4920

    Article  CAS  Google Scholar 

  24. Aston, J. G.; Schumann, S. C.; Fink, H. L.; Doty, P. M., “The structure of Ali- cyclic compounds”, J. Am. Chem. Soc. (1941) 63, 2029–2030

    Article  CAS  Google Scholar 

  25. Aston, J. G.; Fink, H. L.; Schumann, S. C., “The heat Capacity and entropy, heats of transition, fusion and vaporization and the vapor pressures of cyclopentane. Evidence for a non-planar structure”, J. Am. Chem. Soc., (1943) 65, 341–346

    Article  CAS  Google Scholar 

  26. McCullough, J. P., “Pseudorotation in cyclopentane and related molecules”, J. Chem. Phys. (1958) 29, 966–967

    Article  CAS  Google Scholar 

  27. McCullough, J. P.; Pennington, R. E.; Smith, J. C.; Hossenlopp, I. A.; Waddington, G., “Thermodynamics of cyclopentane, methylcyclopentane and 1, cis-3-Dimethyl cyclopentane: Verification of the concept of Pseudorotation”, J. Am. Chem. Soc. (1959) 81, 5880–5883

    Article  CAS  Google Scholar 

  28. Almenningen, A.; Bastiansen, O.; Skancke, P. N., “Preliminary results of an electron diffraction reinvestigation of cyclobutane and cyclopentane ”, Acta Chem. Scand. (1961) 15, 711–712

    Article  CAS  Google Scholar 

  29. Lemieux, R. U., “The configuration and conformation of Thymidine”, Can. J. Chem. (1961) 39, 116–120

    Article  CAS  Google Scholar 

  30. Jardetzky, C. D., “Proton magnetic resonance studies on Purines, Pyrimidines, Ribose Nucleosides and Nucleotides. III. Ribose conformation”, J. Am. Chem. Soc. (1960) 82, 229–233

    Article  CAS  Google Scholar 

  31. Jardetzky, C. D., “N.m.r. of nucleic acid derivatives. V. Deoxyribose conformation”, J. Am. Chem. Soc. (1961) 83, 2919–2920

    Article  CAS  Google Scholar 

  32. Jardetzky, C. D., “Proton magnetic resonance of nucleotides. IV. Ribose conformation”, J. Am. Chem. Soc. (1962) 84, 62–66

    Article  CAS  Google Scholar 

  33. Abraham, R. J.; Hall, L. D.; McLauchlan, K. A., “A proton resonance study of the conformation of carbohydrates in solution. Part I. Derivatives of 1,2-O- Isopropylidene- α -D-xylo-hexofuranose”, J. Chem. Soc. (1962) 3699–3705

    Google Scholar 

  34. Lemieux, R. U., “Rearrangements and Isomerizations in Carbohydrate Chemistry”, In P. de Mayo, ed., “Molecular Rearrangements”, Interscience Division, John Wiley and Sons, New York, 1963, p. 709

    Google Scholar 

  35. Angyal, S. J., “The composition and conformation of sugars in solution”, Angew. Chem. Intern. Ed. (1969) 8, 157–166

    Article  CAS  Google Scholar 

  36. Lemieux, R. U., In “Molecular Rearrangements”, P. De Mayo, ed., Vol 2, Wiley- Interscience, New York, 1963, pp. 710–713

    Google Scholar 

  37. Bishop, C. T.; Cooper, F. P., “Glycosidation of sugars. II. Methanolysis of D-xylose, D-arabinose, D-lyxose, and D-ribose”, Can. J. Chem. (1963) 41. 2743–2758

    Article  Google Scholar 

  38. Smirnyagin, V.; Bishop, C. T., “Glycosidation of sugars. IV. Methanolysis of D- glucose, D-galactose, and D-mannose”, Can. J. Chem. (1968) 46, 3085–3090

    Article  CAS  Google Scholar 

  39. Spencer, M., Acta Cryst. (1959) 12, 59

    Article  CAS  Google Scholar 

  40. Lemieux, R. U.; Nagarajan, R.,“The configuration of Di-D-Fructose Anhydride I”, Can. J. Chem. (1964) 42, 1270–1278

    Article  CAS  Google Scholar 

  41. Hendrickson, J. B., “Molecular geometry. I. Machine Computation of the common rings”, J. Am. Chem. Soc. (1961) 83, 4537–4547

    Article  CAS  Google Scholar 

  42. Anet, F. A. L.; Anet, R., “Conformational Processes in Rings”, in L. M. Jackman and F. A. Cotton, eds. “Dynamic Nuclear Magnetic Resonance Spectroscopy”, Academic Press, New York, 1975, p. 543ff

    Google Scholar 

  43. Sandstrom, J., “Dynamic NMR Spectroscopy”, Academic Press, New York, 1982

    Google Scholar 

  44. Van de Graaf, B.; Baas, J. M. A.; Wepster, B. M., “Studies on cyclohexane derivatives. Part XV. Force field calculations on some tert-butyl substituted cyclohexane compounds”, Rec.Trav. Chim.(Pays-Bas) (1978) 97, 268–273

    Article  Google Scholar 

  45. Van de Graaf, B.; Baas, J. M. A.; Van Veen, A., “Empirical force field calculations. VI. Exploration of reaction paths for the interconversion of conformers. Application to the interconversion of the cyclohexane conformers”, Rec. Trav. Chim. (Pays-Bas) (1980) 99, 175–178

    Article  Google Scholar 

  46. Eliel, E. L.; Allinger. N. L,.Angyal, S. J.; Morrison, G. A., “Conformational Analysis”, Wiley-Interscience, New York, 1965, pp. 351–432

    Google Scholar 

  47. Angyal, S. J., “Conformational analysis in carbohydrate chemistry. I. Conformational free energies. The conformations and α: β ratios of aldopyranoses in aqueous solution”, Aust. J. Chem. (1968) 21, 2737–2746

    Article  CAS  Google Scholar 

  48. Eliel, E. L.; Knoeber, M. C., “Conformational analysis. XVI. 1,3-Dioxanes”, J. Am. Chem. Soc. (1968) 90, 3444–3458

    Article  CAS  Google Scholar 

  49. Angyal, S. J.; McHugh, D. J., “Cyclitols. Part V. Paper ionophoresis, complex formation with borate, and the rate of periodic acid oxidations”, J. Chem. Soc. (1957) 1423–1431

    Google Scholar 

  50. Angyal, S. J.; McHugh, D. J., “Interaction energies of axial hydroxyl groups”, Chem. Ind. (London) (1956) 1147–1148

    Google Scholar 

  51. Angyal, S. J.; Klavins, J. E. unpublished data

    Google Scholar 

  52. Eliel, E. L.; Allinger, N. L.; Angyal, S. J.; Morrison, G. A., “Conformational Analysis”, Wiley-Interscience, New York, 1965, pp. 439–440

    Google Scholar 

  53. Edward, J. T., “Stability of glycosides to acid hydrolysis”, Chem. Ind. (London) (1955) 1102–1104

    Google Scholar 

  54. Lemieux, R. U.; Chü, N. J., Abstr. Papers Amer. Chem. Soc. Meeting (1958) 133, 31 N

    Google Scholar 

  55. Winstein, S.; Holness, N. J., “Neighboring carbon and hydrogen. XIX. t-Butylcyclohexyl Derivatives. Quantitative conformational analysis”, J. Am. Chem. Soc. (1955) 77, 5562–5578

    Article  CAS  Google Scholar 

  56. Eliel, E. L.; Lukacs, C. A., “Conformational analysis. II. Esterification rates of Cy- clohexanols”, J. Am. Chem. Soc. (1957) 79, 5986–5992

    Article  CAS  Google Scholar 

  57. Subbotin, O. A.; Sergeyev, N. M., “Conformational Equilibria in Cyclohexanol, Nitro cyclohexane, and Methylcyclohexane from the Low Temperature 13 C Nuclear Magnetic Resonance Spectra”, J. Chem. Soc. Chem. Commun. (1976) 141–142

    Google Scholar 

  58. Reeves, R. E., “The shape of pyranose rings”, J. Am. Chem. Soc. (1950) 72, 1499–1506

    Article  CAS  Google Scholar 

  59. Reeves, R. E., “Cuprammonium-glycoside complexes”, Adv. Carbohydr. Chem. (1951) 6, 107–134

    CAS  Google Scholar 

  60. Angyal, S. J., “The composition and conformation of sugars in solution”, Angew. Chem. Internat. Ed. (1969) 8, 157–166

    Article  CAS  Google Scholar 

  61. Perlin, A. S., “Hydroxyl proton magnetic resonance in relation to ring size, Substituent groups, and mutarotation of carbohydrates”, Canad. J. Chem. (1966) 44, 539–550

    Article  CAS  Google Scholar 

  62. Mackie, W.; Perlin, A. S., “Pyranose-Furanose and Anomeric Equilibria: Influence of solvent and of partial methylation”, Canad. J. Chem. (1966) 44, 2039–2049

    Article  CAS  Google Scholar 

  63. Lemieux, R. U.; Stevens, J. D., “The proton magnetic resonance spectra and tautomeric equilibria of aldoses in deuterium oxide”, Can. J. Chem. (1966) 44, 249–262

    Article  CAS  Google Scholar 

  64. Rudrum, M.; Shaw, D. F., “The structure and conformation of some monosaccharides in solution”, J. Chem. Soc. (1965) 52–57

    Google Scholar 

  65. Angyal, S. J.; Pickles, V. A.; Ahluwahlia, R., “Interaction energy between an axial methyl and an axial hydroxyl group in pyranoses”, Carbohydr. Res. (1966) 1, 365–370

    Article  CAS  Google Scholar 

  66. Angyal, S. J., “Conformational analysis in carbohydrate chemistry. I. Conformational free energies. The conformations and α: β ratios of aldopyranoses in aqueous solution”, Aust. J. Chem. (1968) 21, 2737–2746

    Article  CAS  Google Scholar 

  67. Brady, J. W., “Molecular dynamics simulations of alpha-D-glucose in aqueous solution”, J. Am. Chem. Soc. (1989) 111, 5155–5165

    Article  CAS  Google Scholar 

  68. Ha, S.; Gao, J.; Tidor, B.; Brady, J. W.; Karplus, M., “Solvent effect on the anomeric equilibrium in D-glucose: a free energy simulation analysis ”, J. Am. Chem. Soc. (1991) 113, 1553–1557

    Article  CAS  Google Scholar 

  69. Polavarapu, P. L.; Ewig, C. S., “Ab Initio computed molecular structures and energies of the conformers of glucose”, J. Comput. Chem. (1992) 13, 1255–1261

    Article  CAS  Google Scholar 

  70. Zheng, Y.-J.; Le Grand, S. M.; Merz, K. M., “Conformational preferences for hydroxyl groups in substituted tetrahydropyrans”, J. Comput. Chem. (1992) 13, 772–791

    Article  CAS  Google Scholar 

  71. Glennon, T. M.; Zheng, Y.-J.; LeGrand, S. M.; Shutzberg, B. A.; Merz, K. M., “A force field for monosaccharides and (1 ➝ 4) linked polysaccharides”, J. Comput. Chem. (1994) 9, 1019–1040

    Article  Google Scholar 

  72. Barrows, S. E.; Dulles, F. J.; Cramer, C. J.; French, A. D.; Truhlar, D. G., “Relative stability of alternative chair forms and hydroxymethyl conformations of β-Image- glucopyranose”, Carbohydr. Res.(1995) 276, 219–251

    Article  CAS  Google Scholar 

  73. Woods, R. J.; Raymond A. D.; Edge, C. J.; Fraser-Reid, B., “Molecular mechanical and molecular dynamic simulations of glycoproteins and oligosaccharides. 1. GLYCAM_93 parameter development”, J. Phys. Chem. (1995) 99, 3832–3846

    Article  CAS  Google Scholar 

  74. Woods, R. J.; Smith, V. H.; Szarek, W. A.; Farazdel, A., “Ab initio LCAO-MO calculations on α -D-glucopyranose, β -D-fructopyranose, and their thiopyranoid-ring analogs. Application to a theory of sweetness”, J. Chem. Soc., Chem. Commun. (1987) 12, 937–939

    Article  Google Scholar 

  75. Senderowitz, H.; Parish, C.; Still, W. C, “Carbohydrates: United Atom AMBER* Pa- rameterization of Pyranoses and Simulations Yielding Anomeric Free Energies”, J. Am. Chem. Soc. (1996) 118, 2078–2086

    Article  CAS  Google Scholar 

  76. Reiding, S.; Schlenkrich, M.; Brickman, J., “Force field parameters for carbohydrates”, J. Comput. Chem. (1996) 17, 450–468

    Article  Google Scholar 

  77. Ott, K.-H.; Meyer, B., “Parametrization of GROMOS force field for oligosaccharides”, J. Comput. Chem. (1996) 17, 1068–1084

    Article  CAS  Google Scholar 

  78. Damm, W.; Frontera A.; Tirado-Rives, J.; Jorgensen, W. L., “OPLS all-atom force field for carbohydrates”, J. Comput. Chem. (1997) 18, 1955–1970

    Article  CAS  Google Scholar 

  79. Lii, J.-H.; Chen, K.-H.; Allinger, N. L., “Alcohols, ethers, carbohydrates, and related compounds. IV. Carbohydrates”, J. Comput. Chem. (2003) 24, 1504–1513

    Article  CAS  Google Scholar 

  80. Guler, L. P.; Yu, Y.-Q.; Kenttämaa, H. I.,“An experimental and computational study of the gas-phase structures of five-carbon Monosaccharides”, J. Phys. Chem. A (2002) 106, 6754–6764

    Article  CAS  Google Scholar 

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  1. Department of Biochemistry & Molecular Biology, Pennsylvania State University, H171, Milton S. Hershey Medical Center, 500 University Drive, 17033, Hershey, PA, USA

    Momcilo Miljković

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Miljković, M. (2010). Conformational Analysis of Monosaccharides. In: Carbohydrates. Springer, New York, NY. https://doi.org/10.1007/978-0-387-92265-2_2

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