Synthesis of potential inhibitors of glycosyltransferases representing UDP-GlcNAc
-
Marek Baráth
,
Miroslav Koóš
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.ch2Search 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.2012.06.007Search 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.2014.05.003Search 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/jo00355a026Search 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/s11696-009-0008-8Search 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)90003-7Search 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.2001.024Search 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.Search 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.Search 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.2005.01.041Search 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;2-6Search 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-FSearch in Google Scholar
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- Analytical procedure for steroid profiling valid for Athlete Biological Passport
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