Skip to main content
SpringerLink
Log in
Book cover

Bioactive Conformation I pp 169–185Cite as

NMR Analysis of Bioprotective Sugars: Sucrose and Oligomeric (1→2)-α-D-glucopyranosyl-(1→2)-β-D-fructofuranosides

  • Chapter
  • First Online:

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 272))

Abstract

NMR spectroscopy yields structural information on a new class of bioprotectants with the general composition oligo(1 → 2)-α-d-glucopyranosyl-(1 → 2)-β-d-fructofuranoside. Their smallest representative is sucrose for which conflicting models try to explain its cryoprotective properties. Starting from sucrose, we characterize the influence of the growing chain of oligo(1 → 2)-α-d-glucopyranoses. An analytical approach will be presented that can identify ultraweak membrane affinities, a property often discussed in the context of cryoprotectants. The most prominent feature of the vicinally connected (1 → 2)-α-d-glucopyranose oligomers is their well-defined solution structure with a stand-alone sugar helix. The unfolding barrier of this helix is large enough to become observable as line-broadening in the 1H NMR.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Bryant G, Koster KL, Wolfe J (2001) Seed Science Res 11:17

    CAS  Google Scholar 

  2. Vereyken IJ, Chupin V, Hoekstra FA, Smeekens SCM, Kruijff B (2003) Biophys J 84:3759

    Article  CAS  Google Scholar 

  3. Furuki T (2002) Carbohydr Res 337:441

    Article  CAS  Google Scholar 

  4. Hincha DK, Zuther E, Hellwege EM, Heyer AG (2002) Glycobiology 12:103

    Article  CAS  Google Scholar 

  5. Bock K, Lemieux RU (1982) Carbohydr Res 100:63

    Article  CAS  Google Scholar 

  6. Freedberg DI (2002) J Am Chem Soc 124:2538

    Article  CAS  Google Scholar 

  7. Venable RM, Delaglio F, Norris SE, Freedberg DI (2005) Carbohydr Res 340:863

    Article  CAS  Google Scholar 

  8. Poppe L, van Halbeek H (1992) J Am Chem Soc 114:1092

    Article  CAS  Google Scholar 

  9. Immel S, Lichtenthaler FW (1995) Liebigs Ann Chem 1925

    Google Scholar 

  10. Symons MCR, Benbow JA, Harvey JM (1980) Carbohydr Res 83:9

    Article  CAS  Google Scholar 

  11. Poppe L, van Halbeek H (1991) J Am Chem Soc 113:363

    Article  CAS  Google Scholar 

  12. Poppe L, van Halbeek H (1994) Nature Struct Biol 4:215

    Article  Google Scholar 

  13. Sandström C, Baumann H, Kenne L (1998) J Chem Soc Perkin Trans 2 4:809

    Article  Google Scholar 

  14. Bekiroglu S, Kenne L, Sandström C (2003) J Org Chem 68:1671

    Article  CAS  Google Scholar 

  15. Adams B, Lerner L (1992) J Am Chem Soc 114:4827

    Article  CAS  Google Scholar 

  16. Leeflang BR, Vliegenthart JFG, Kroon-Batenburg LMJ, van Eijck BP, Kroon J (1992) Carbohydr Res 230:41

    Article  CAS  Google Scholar 

  17. Bock K, Frejd T, Kihlberg J, Magnusson G (1988) Carbohydr Res 176:253

    Article  CAS  Google Scholar 

  18. Dabrowski J, Kožár T, Grosskurth H, Nifant'ev NE (1995) J Am Chem Soc 117:5534

    Article  CAS  Google Scholar 

  19. Middleton DA, Reid DG, Watts A (2004) J Pharm Sci 93:507

    Article  CAS  Google Scholar 

  20. Wang J, Schnell JR, Chou J (2004) J Biochem Biophys Res Commun 324:212

    Article  CAS  Google Scholar 

  21. Middleton DA, Hughes E, Madine J (2004) J Am Chem Soc 126:9478

    Article  CAS  Google Scholar 

  22. Morton CJ, Campbell ID (1994) Curr Biol 4:615

    Article  CAS  Google Scholar 

  23. McLendon G (1991) Struct Bond 75:159

    CAS  Google Scholar 

  24. Kim KH, Thomas DW (1988) J Immunol 140:2500

    CAS  Google Scholar 

  25. Simons K, Ikonen E (1997) Nature 387:569

    Article  CAS  Google Scholar 

  26. Fischer D, Geyer A (2005) Magn Reson Chem 45:893

    Article  CAS  Google Scholar 

  27. Johnson CS (1999) Prog NMR Spectrosc 34:203

    Article  CAS  Google Scholar 

  28. Yan J, Kline AD, Mo H, Zartler ER, Shapiro MJ (2002) J Am Chem Soc 124:9984

    Article  CAS  Google Scholar 

  29. Diaz MD, Berger S (2000) Carb Res 329:1

    Article  CAS  Google Scholar 

  30. Klein J, Meinecke R, Mayer M, Meyer B (1999) J Am Chem Soc 121:5336

    Article  CAS  Google Scholar 

  31. Vogtherr M, Peters T (2000) J Am Chem Soc 122:6093

    Article  CAS  Google Scholar 

  32. Mayer M, Meyer B (1999) Angew Chem Int Ed 38:1784

    Article  CAS  Google Scholar 

  33. Campbell AP, Sykes BD (1993) Ann Rev Biophys Biomol Struct 22:99

    Article  CAS  Google Scholar 

  34. Ni F (1994) Prog NMR Spectrosc 26:517

    Article  CAS  Google Scholar 

  35. Tjandra N, Bax A (1997) Science 278:1111

    Article  CAS  Google Scholar 

  36. Prestegard JH, Al-Hashimi HM, Tolman JR (2000) Quart Rev Biophys 33:371

    Article  CAS  Google Scholar 

  37. Tolman JR (2001) Curr Opin Struct Biol 11:532

    Article  CAS  Google Scholar 

  38. Simon B, Sattler M (2002) Angew Chem Int Ed 41:437

    Article  CAS  Google Scholar 

  39. Koenig BW (2002) ChemBioChem 3:975

    Article  CAS  Google Scholar 

  40. Bolon PJ, Al-Hashimi HM, Prestegard JH (1999) J Mol Biol 293:107

    Article  CAS  Google Scholar 

  41. Koenig BW, Mitchell DC, König S, Grzesiek S, Litman BJ, Bax A (2000) J Biomol NMR 16:121

    Article  CAS  Google Scholar 

  42. Koenig BW, Kontaxis G, Mitchell DC, Louis JM, Litman BJ, Bax A (2002) J Mol Biol 322:441

    Article  CAS  Google Scholar 

  43. Shimizu H, Donohue-Rolfe A, Homans SW (1999) J Am Chem Soc 121:5815

    Article  CAS  Google Scholar 

  44. Sanders CR II, Schwonek JP (1992) Biochemistry 31:8898

    Article  CAS  Google Scholar 

  45. Ottiger M, Bax A (1998) J Biomol NMR 12:361

    Article  CAS  Google Scholar 

  46. Sanders C, Hare B, Howard K, Prestegard JH (1994) Prog NMR Spectrosc 26:421

    Article  CAS  Google Scholar 

  47. Brunner E (2001) Conc Magn Reson 13:238

    Article  CAS  Google Scholar 

  48. Rowe BA, Neal SL (2003) Langmuir 19:2039

    Article  CAS  Google Scholar 

  49. Gaemers S, Bax A (2001) J Am Chem Soc 123:12343

    Article  CAS  Google Scholar 

  50. Neubauer H, Meiler J, Peti W, Griesinger C (2001) Helv Chim Acta 84:243

    Article  CAS  Google Scholar 

  51. Rundlöf T, Landersjö C, Lycknert K, Maliniak A, Widmalm G (1998) Magn Reson Chem 36:773

    Article  Google Scholar 

  52. Martin-Pastor M, Bush CA (2000) Biochemistry 39:4674

    Article  CAS  Google Scholar 

  53. Thompson GS, Shimizu H, Homans SW, Donohue-Rolfe A (2000) Biochemistry 39:13153

    Article  CAS  Google Scholar 

  54. Tian F, Al-Hashimi HM, Craighead JL, Prestegard JH (2001) J Am Chem Soc 123:485

    Article  CAS  Google Scholar 

  55. Geyer A, Bockelmann D, Weissenbach K, Fischer H (1999) Tetrahedron Lett 40:477

    Article  CAS  Google Scholar 

  56. Geyer A, Moser F (2000) Eur J Org Chem 7:1113

    Article  Google Scholar 

  57. Lambruschini C, Relini A, Ridi A, Cordone L, Ghiozzi A (2000) Langmuir 16:5467

    Article  CAS  Google Scholar 

  58. Engel A, Bendas G, Wilhelm F, Mannova M, Ausborn M, Nuhn P (1994) Int J Pharm 107:99

    Article  CAS  Google Scholar 

  59. Santarius KA (1996) Cryobiology 33:118

    Article  CAS  Google Scholar 

  60. Turner S, Senaratna T, Touchell D, Bunn E, Dixon K, Tan B (2001) Plant Sci 160:489

    Article  CAS  Google Scholar 

  61. Stevens CV, Meriggi A, Booten K (2001) Biomacromolecules 2:1

    Article  CAS  Google Scholar 

  62. Brumfiel G (2004) Nature 428:14

    Article  CAS  Google Scholar 

  63. Fischer D, Geyer A, Loos E (2006) FEBS J 273:137

    Article  CAS  Google Scholar 

  64. Chaen H, Nishimoto T, Nakada T, Tetsuya F, Fukuda S, Kurimoto M, Tsujisaka Y (2001) J Biosci Bioeng 92:177

    Article  CAS  Google Scholar 

  65. Watanabe T, Kamo Y, Yoshihiro M, Matsuda K, Dudman WF (1982) Carbohydr Res 110:170

    Article  CAS  Google Scholar 

  66. Lütteke T, Frank M, Lieth C-W v. d. (2005) Nucleic Acid Res 33:D242

    Article  CAS  Google Scholar 

  67. HyperChem. Hypercube, Gainesville, FL

    Google Scholar 

  68. Janke RH, Haufe G, Würthwein EU, Borkent JH (1996) J Am Chem Soc 118:6031

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Deutsche Forschungsgemeinschaft. The authors thank Dr. Eckhard Loos and Edelgard Herold for the isolation of the oligo-(1→2)-α-d-glucopyranosyl-(1→2)-β-d-fructofuranosides.

Author information

Authors and Affiliations

  1. Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse, 35032, Marburg, Germany

    Daniela Fischer & Armin Geyer

Authors
  1. Daniela Fischer
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Armin Geyer
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Armin Geyer .

Editor information

Thomas Peters

Rights and permissions

Reprints and permissions

Copyright information

© 2006 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Fischer, D., Geyer, A. (2006). NMR Analysis of Bioprotective Sugars: Sucrose and Oligomeric (1→2)-α-D-glucopyranosyl-(1→2)-β-D-fructofuranosides. In: Peters, T. (eds) Bioactive Conformation I. Topics in Current Chemistry, vol 272. Springer, Berlin, Heidelberg . https://doi.org/10.1007/128_062

Download citation

Publish with us

Policies and ethics

Search

Navigation