Startseite Lebenswissenschaften Synthesis of potential inhibitors of glycosyltransferases representing UDP-GlcNAc
Artikel
Lizenziert
Nicht lizenziert Erfordert eine Authentifizierung

Synthesis of potential inhibitors of glycosyltransferases representing UDP-GlcNAc

  • Marek Baráth EMAIL logo , Miroslav Koóš , Igor Tvaroška und Ján Hirsch
Veröffentlicht/Copyright: 12. Dezember 2014
Veröffentlichen auch Sie bei De Gruyter Brill

Abstract

Based on rational design of the transition state analog inhibitors of glycosyltransferases, four model glycomimetics of this type, viz. benzyl 2-thio-α-D-fructofuranoside 1-diethylphosphate (XIa), its β-anomer (XIb), and their ethyl 2-thio analogs - α-anomer (XIIa) and β-anomer (XIIb), were synthesized. In addition, fourteen precursors arising during the synthesis of the desired final model compounds (XI and XII), partially or fully acetylated benzyl and/or ethyl 2-thiofructofuranoside 1-diethyl phosphates, were isolated and characterized with the aim to prepare complete series of glycomimetics, representing donor UDP-GlcNAc designated for biological assays on human GnT’s, viz. GnT-I, Core2GnT, and GnT-V.

References

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 relationship. Advances in Enzymology and Related Areas of Molecular Biology, 52, 23-175. DOI: 10.1002/9780470122976.ch2.10.1002/9780470122976.ch2Suche in Google Scholar

Breton, C., Fournel-Gigleux, S., & Palcic, M. M. (2012). Recent structures, evolution and mechanisms of glycosyltransferases. Current Opinion in Structural Biology, 22, 540-549. DOI: 10.1016/j.sbi.2012.06.007.10.1016/j.sbi.2012.06.007Suche in Google Scholar

Hadley, B., Maggioni, A., Ashikov, A., Day, C. J., Haselhorst, T., & Tiralongo, J. (2014). Structure and function of nucleotide sugar transporters: Current progress. Computational and Structural Biotechnology Journal, in press. DOI: 10.1016/j.csbj.2014.05.003.10.1016/j.csbj.2014.05.003Suche in Google Scholar

Herzig, J., Nudelman, A., Gottlieb, H. E., & Fischer, B. (1986). Studies in sugar chemistry. 2. A simple method for Odeacetylation of polyacylated sugars. Journal of Organic Chemistry, 51, 727-730. DOI: 10.1021/jo00355a026.10.1021/jo00355a026Suche in Google Scholar

Hirsch, J., Koóš, M., & Tvaroška, I. (2009). Synthesis of saccharide precursors for preparation of potential inhibitors of glycosyltransferases. Chemical Papers, 63, 329-335. DOI: 10.2478/s11696-009-0008-8.10.2478/s11696-009-0008-8Suche in Google Scholar

Kleene, R., & Berger, E. G. (1993). The molecular and cell biology of glycosyltransferases. Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes, 1154, 283-325. DOI: 10.1016/0304-4157(93)90003-7.10.1016/0304-4157(93)90003-7Suche in Google Scholar

Marquardt, T., & Freeze, H. (2001). Congenital disorders of glycosylation: Glycosylation defects in man and biological models for their study. Biological Chemistry, 382, 161-177.10.1515/BC.2001.024Suche in Google Scholar

Montreuil, J., Vliegenthart, J. F. G., & Schachter, H. (1995) Glycoproteins (Series: New comprehensive biochemistry, Vol. 29, Part A). Amsterdam, The Netherlands: Elsevier.Suche in Google Scholar

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

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.2005.01.041.10.1016/j.carres.2005.01.041Suche in Google Scholar

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;2-6.10.1002/(SICI)1521-3773(19990816)38:16<2300::AID-ANIE2300>3.0.CO;2-6Suche in Google Scholar

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. 10.1002/1521-3773(20011105)40:21<4007::AID-ANIE4007>3.0.CO;2-FSuche in Google Scholar

Received: 2014-5-29
Revised: 2014-8-8
Accepted: 2014-8-13
Published Online: 2014-12-12
Published in Print: 2015-2-1

© 2015 Institute of Chemistry, Slovak Academy of Sciences

Artikel in diesem Heft

  1. Selection and design of ionic liquids as solvents in extractive distillation and extraction processes
  2. Analytical procedure for steroid profiling valid for Athlete Biological Passport
  3. Fabrication of paper-based analytical device by silanisation of filter cellulose using alkyltrimethoxysilane coupled with UV radiation
  4. Synthesis, characterisation and photocatalytic activity of Ag+- and Sn2+-substituted KSbTeO6
  5. Dysprosium pertraction through facilitated supported liquid membrane using D2EHPA as carrier
  6. Volatile compounds composition and antioxidant activity of bee pollen collected in Lithuania
  7. Self-penetrating and interpenetrating 3D metal–organic frameworks constructed from 4-(4-carboxyphenoxy)-phthalic acid and N-donor auxiliary ligands
  8. Preparation of ceramic γ-Al2O3–TiO2 nanofiltration membranes for desalination
  9. Promoting effect of group VI metals on Ni/MgO for catalytic growth of carbon nanotubes by ethylene chemical vapour deposition
  10. Microwave-assisted solvent-free synthesis and luminescence properties of 2-substituted-4,5-di(2-furyl)-1H-imidazoles
  11. Synthesis of potential inhibitors of glycosyltransferases representing UDP-GlcNAc
  12. Development of transition state analogue inhibitors for N-acetylglycosyltransferases bearing D-psicoor D-tagatofuranose scaffolds
  13. Efavirenz–eudragit E-100 nanoparticle-loaded aerosol foam for sustained release: in-vitro and ex-vivo evaluation
  14. Photochromic and molecular switching behaviour of Schiff base-containing pyrazolone ring
  15. Improvements to CO2 headspace biodegradability test
  16. Synthesis of corn rootworm pheromones from commercial diols
Heruntergeladen am 9.3.2026 von https://www.degruyterbrill.com/document/doi/10.1515/chempap-2015-0017/html
Button zum nach oben scrollen