Startseite Synthesis of saccharide precursors for preparation of potential inhibitors of glycosyltranferases
Artikel
Lizenziert
Nicht lizenziert Erfordert eine Authentifizierung

Synthesis of saccharide precursors for preparation of potential inhibitors of glycosyltranferases

  • Ján Hirsch EMAIL logo , Miroslav Koóš und Igor Tvaroška
Veröffentlicht/Copyright: 25. März 2009
Veröffentlichen auch Sie bei De Gruyter Brill

Abstract

Ethyl 6-O-tert-butyldimethylsilyl-3,4-di-O-acetyl-2-thio-α-D-fructofuranoside (Va), its β-analog (Vb); as well as benzyl 6-O-tert-butyldimethylsilyl-3,4-di-O-acetyl-2-thio-α-D-fructofuranoside (Xa) and its β-analog (Xb), having an unprotected OH group at C-1, were prepared by sequential synthesis starting from commercially available D-fructose. These compounds represent suitable nucleophiles for the preparation of model carbohydrate mimetics of a glycosyltransferase inhibitor type in transition state. The structures of all compounds were confirmed by NMR spectral data and elemental analyses.

[1] Beyer, T. A., Sadler, J. E., Rearick, J. I., Paulson, J. C., & Hill, R. L. (1981). Glycosyltransferases and their use in assessing oligosaccharide structure and structure-function relationships. Advances in Enzymology and Related Areas of Molecular Biology, 52, 23–175. http://dx.doi.org/10.1002/9780470122976.ch210.1002/9780470122976.ch2Suche in Google Scholar

[2] Bouali, A., Descotes, G., Ewing, D. F., Grouiller, A., Lefkidou, J., Lespinasse, A. D., & Mackenzie, G. (1992). Derivatisation of 1,3,4,6-tetra-O-benzoyl-α-D-fructofuranose at the anomeric site: O-alkylation, O-acylation, O-arylation, amination and selenation reactions. Journal of Carbohydrate Chemistry, 11, 159–169. DOI: 10.1080/07328309208017797. http://dx.doi.org/10.1080/0732830920801779710.1080/07328309208017797Suche in Google Scholar

[3] Kleene, R., & Berger, E. G. (1993). The molecular and cell biology of glycosyltransferases. Biochimica et Biophysica Acta - Reviews on Biomembranes, 1154, 283–325. DOI: 10.1016/0304-4157(93)90003-7. http://dx.doi.org/10.1016/0304-4157(93)90003-710.1016/0304-4157(93)90003-7Suche in Google Scholar

[4] Krog-Jensen, C., & Oscarson, S. (1996). Synthesis of D-fructofuranosides using thioglycosides as glycosyl donors. Journal of Organic Chemistry, 61, 1234–1238. DOI: 10.1021/jo951641t. http://dx.doi.org/10.1021/jo951641t10.1021/jo951641tSuche in Google Scholar

[5] Montreuil, J., Vliegenthart, J. F. G., & Schachter, H. (Eds.) (1995). Glycoproteins I. New comprehensive biochemistry, Vol. 29A. Amsterdam: Elsevier. Suche in Google Scholar

[6] Montreuil, J., Vliegenthart, J. F. G., & Schachter, H. (Eds.) (1996). Glycoproteins and disease. New comprehensive biochemistry, Vol. 30. Amsterdam: Elsevier. Suche in Google Scholar

[7] Moody, W., & Richards, G. N. (1983). Formation and equilibration of D-fructosides and 2-thio-D-fructosides in acidified dimethyl sulfoxide: synthetic and mechanistic aspects. Carbohydrate Research, 124, 201–213. DOI: 10.1016/0008-6215(83)88456-0. http://dx.doi.org/10.1016/0008-6215(83)88456-010.1016/0008-6215(83)88456-0Suche in Google Scholar

[8] Oscarson, S., & Sehgelmeble, F. W. (2000). A novel β-directing fructofuranosyl donor concept. Stereospecific synthesis of sucrose. Journal of the American Chemical Society, 122, 8869–8872. DOI: 10.1021/ja001439u. http://dx.doi.org/10.1021/ja001439u10.1021/ja001439uSuche in Google Scholar

[9] Raab, M., Kozmon, S., & Tvaroška, I. (2005). Potential transition-state analogs for glycosyltransferases. Design and DFT calculations of conformational behavior. Carbohydrate Research, 340, 1051–1057. DOI: 10.1016/j.carres.2005.01.041. http://dx.doi.org/10.1016/j.carres.2005.01.04110.1016/j.carres.2005.01.041Suche in Google Scholar

[10] Sears, P., & Wong, C.-H. (1999). Carbohydrate mimetics: A new strategy for tackling the problem of carbohydratemediated biological recognition. Angewandte Chemie International Edition, 38, 2300–2324. DOI: 10.1002/(SICI)1521-3773(19990816)38:16〈2300::AID-ANIE2300〉3.0.CO;2-6. http://dx.doi.org/10.1002/(SICI)1521-3773(19990816)38:16<2300::AID-ANIE2300>3.0.CO;2-610.1002/(SICI)1521-3773(19990816)38:16<2300::AID-ANIE2300>3.0.CO;2-6Suche in Google Scholar

[11] Waldscheck, B., Strieff, M., Notz, W., Kinzy, W., & Schmidt, R. R. (2001). α(1–3)-Galactosyltransferase inhibition based on a new type of disubstrate analogue. Angewandte Chemie International Edition, 40, 4007–4011. DOI: 10.1002/1521-3773(20011105)40:21〈4007::AID-ANIE4007〉3.0.CO;2-F. http://dx.doi.org/10.1002/1521-3773(20011105)40:21<4007::AID-ANIE4007>3.0.CO;2-F10.1002/1521-3773(20011105)40:21<4007::AID-ANIE4007>3.0.CO;2-FSuche in Google Scholar

Published Online: 2009-3-25
Published in Print: 2009-6-1

© 2008 Institute of Chemistry, Slovak Academy of Sciences

Artikel in diesem Heft

  1. Application of isotachophoretic and conductometric methods for neomycin trisulphate determination
  2. A rhodamine-based Hg2+-selective fluorescent probe in aqueous solution
  3. A simple flow injection spectrophotometric determination method for iron(III) based on O-acetylsalicylhydroxamic acid complexation
  4. Global optimization for parameter estimation of differential-algebraic systems
  5. Effect of ethyl acetate on carbohydrate components and crystalline structure of pulp produced in aqueous acetic acid pulping
  6. Effects of acyl donor type, catalyst type, and reaction conditions on the activity and selectivity of Friedel-Crafts acylation
  7. Intramolecular MLOH/π and MLNH/π interactions in crystal structures of metal complexes
  8. A strategy for new macrocycle magnetic materials synthesis
  9. Rearrangement of N-(3-pyridyl)nitramine
  10. New Cu(II), Co(II), and Ni(II) complexes with thieno[2,3-b]pyridine and 2-methylthieno[2,3-b]pyridine as ligands: Synthesis and crystal structures
  11. Synthesis of saccharide precursors for preparation of potential inhibitors of glycosyltranferases
  12. Simultaneous spectrophotometric determination of minoxidil and tretinoin by the H-point standard addition method and partial least squares
  13. Adsorption and release of terbinafine hydrochloride: Effects of adsorbents, additives, pH, and temperature
  14. Determination of alkaloids in Corydalis yanhusuo using hollow-fibre liquid phase microextraction and high performance liquid chromatography
  15. Chemiluminescence mechanisms of cerium-norfloxacin and its application in urine analysis
  16. A rapid in vitro assay of cobalamin in human urine and medical tablets using ICP-MS
  17. Inverse gas chromatographic characterization of Porapak Q as an extractant of pollutants from aqueous media
Heruntergeladen am 27.11.2025 von https://www.degruyterbrill.com/document/doi/10.2478/s11696-009-0008-8/pdf?lang=de
Button zum nach oben scrollen