Laboratory of Glycoconjugate Chemistry (N52)
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Laboratory Head Nikolay E. Nifantiev, Prof., Associate Member of RAS Tel/fax +7(499)1358784, e-mail:nen@ioc.ac.ru |
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Laboratory (before 2004 — a research group) was established in 1995 by its present leader.
Research areas
Synthesis, structural and conformational analysis of oligo- and polysaccharides and glycoconjugates sourced from them, glycotechnology, glycobiology, rational design of drugs with a target mechanism of action, glycomimetics, conjugated carbohydrate onco-, myco- and bacterial vaccines, diagnosticums for the detection of carbohydrate antigens and anti-carbohydrate antibodies, artificial receptors for screening (HTPS on different technology platforms) and carbohydrate ligands for bioinformatics, bioorganic chemistry of low-molecular non-carbohydrate compounds, wood chemistry, high value-added processing of renewable vegetable feedstock, reagents forapplications in environmental science, agriculture, food production, and in the energy sector.
Selected publications
2014
V.B. Krylov, D.A. Argunov, D.Z. Vinnitskiy, S.A. Verkhnyatskaya, A.G. Gerbst, N.E. Ustyuzhanina, A.S. Dmitrenok, J. Huebner, O. Holst, H.-C. Siebert, and N.E. Nifantiev*, “Pyranoside-into-Furanoside Rearrangement: New Reaction in Carbohydrate Chemistry and Its Application in Oligosaccharide Synthesis”, Chem. Eur. J., 20 (2014) 16516-16522. Cтатье посвящен рисунок на обложке выпуска журнала: http://onlinelibrary.wiley.com/doi/10.1002/chem.201490209/pdf
N. E. Ustyuzhanina, M. I. Bilan, N. A. Ushakova, A. I. Usov, M. V. Kiselevskiy, N. E. Nifantiev* «Fucoidans: pro- or antiangiogenic agents?» Glycobiology 24 (2014) 1265-1274. (Обзор)
B.S. Komarova, M.V. Orekhova, Y.E. Tsvetkov, and N.E. Nifantiev* «Is an Acyl Group at O-3 in Glucosyl Donors Able to Control α-Stereoselectivity of Glycosylation? The Role of Conformational Mobility and the Protecting Group at O-6», Carbohydr. Res. 384 (2014) 70-86.
G. Loers, D. V. Yashunsky, N. E. Nifantiev*, and M. Schachner* «Neural Cell Activation by Phenolic Compounds from the Siberian Larch (Larix sibirica)» J. Nat. Prod. 77 (2014) 1554-1561.
T. Saha, A. Roy,M.L. Gening, D.V. Titov, A.G. Gerbst, Y.E. Tsvetkov, N.E. Nifantiev*, and P. Talukdar* «Cyclo-oligo-(1→6)-β-D-Glucosamine Based Artificial Channels for Tunable Transmembrane Ion Transport» Chem. Commun., 50 (2014) 5514-5516.
Xi Lu, D. Skurnik, C. Pozzi, D. Roux, C. Cywes-Bentley, J. Ritchie, D. Munera, M. Gening, Y. Tsvetkov, N. Nifantiev, M. Waldor, and G. Pier «A poly-N-acetyl glucosamine-Shiga toxin broad spectrum conjugate vaccine for Shiga toxin producing Escherichiacoli» mBio, 5 (2014) e00974-14. DOI: 10.1128/mBio00974-14.
N.E. Ustyuzhanina, N.A. Ushakova, M.E. Preobrazhenskaya, M.I. Bilan, E.N. Tsvetkova, V.B. Krylov, N.A. Anisimova, M.V. Kiselevskiy, Nadezhda V. Krukovskaya, C. Li, G. Yu, S. Saran, R.K. Saxena, A.I. Usov, and N.E. Nifantiev* «Fucoidans as a platform for new anticoagulant drugs discovery» Pure Appl. Chem., 86 (2014) 1365-1375.
V.B. Krylov, D.A. Argunov and N.E. Nifantiev*, «Preparative synthesis of selectively substituted 1,6-anhydro-α-d-galactofuranose derivatives based on the pyranoside-into-furanoside rearrangement», Mendel. Commun., 24 (2014) 336-337.
2013
C. Cywes-Bentley, D. Skurnik, T. Zaidi, D. Roux, R.B. DeOliveira, W.S. Garrett, X. Lu, J. O’Malley, K. Kinzel, T. Zaidi, A. Rey, C. Perrin, R.N. Fichorova, A.K.K. Kayatani, T. Maira-Litran, M.L. Gening,Y.E. Tsvetkov, N.E. Nifantiev, L. Bakaletz, S.I. Pelton, D. Golenbock, and G.B. Pier, «Antibody to a Conserved Antigenic Target is Protective Against Diverse Prokaryotic and Eukaryotic Pathogens» Proc. Natl. Acad. Sci. USA, 110 (2013), E2209-E2218. PNAS PLUS Significance Statements, PNAS 110 (2013) 9631-9632.
M.L. Gening, Y.E. Tsvetkov, D.V. Titov, A.G. Gerbst, O.N. Yudina, A.A. Grachev, A.S. Shashkov, S. Vidal, A. Imberty,T. Saha, D. Kand, P. Talukdar, G.B. Pier, and N.E. Nifantiev, “Linear and cyclic oligo-β-(1→6)-D-glucosamines: synthesis, conformations and applications for design of a vaccine and oligodentate glycoconjugates”, PureAppl. Chem., 85 (2013) 1879-1891.
D.V. Titov, M.L. Gening, A.G. Gerbst, A.O. Chizhov, Y.E. Tsvetkov, and N.E. Nifantiev “Stereochemistry of intramolecular cyclization of tetra-b-(1®6)-D-glucosamines and related tetrasaccharides: the role of the conformational stereocontrol and the neighboring group participation”, Carbohydr. Res. 381 (2013) 161-178.
B.S. Komarova, S.S. Maryasina, Y.E. Tsvetkov, and N. E. Nifantiev, “Water-dependent reduction of carbohydrate azides by dithiothreitol“, SYNTHESIS, 45 (2013) 471-478.
A.G. Gerbst, A.A. Grachev, D.V. Yashunsky, Y.E. Tsvetkov, A.S. Shashkov, N.E. Nifantiev “Theoretical and experimental conformational studies of oligoglucosides structurally related to fragments of fungal cell wall β-(1→3)-D-glucan”, J. Carbohydr. Chem. 32 (2013) 205-221.
B.S. Komarova, N.E. Ustyuzhanina, Y.E. Tsvetkov, and N.E. Nifantiev, “Stereocontrol of 1,2-cis-Glycosylation by Remote O-Acyl Protecting Groups”, in S. Vidal and D. Wertz ed. “Modern Synthetic Methods in Carbohydrate Chemistry – From Monosaccharides to Complex Glycoconjugates”, Wiley, (2013) 125-159. (глава в книге)
M.L. Gening, D.V. Titov, S. Cecioni, A. Audfray, A.G. Gerbst, Y.E. Tsvetkov, V.B. Krylov, A. Imberty, N.E. Nifantiev, S. Vidal, « Synthesis of Multivalent Carbohydrate-Centered Glycoclusters as Nanomolar Ligands of the Bacterial Lectin LecA from Pseudomonas aeruginosa», Chem. Eur. J., 19 (2013) 9272-9275. Данной статье посвящен рисунок на обложке журнала http://onlinelibrary.wiley.com/doi/10.1002/chem.201390104/pdf
L. Paulovičová, E. Paulovičová, A. A. Karelin, Y. E. Tsvetkov, N. E. Nifantiev, S. Bystrický «Effect of Branched α-Oligomannoside Structures on Induction of Anti-Candida Humoral Immune Response», Scand. J. Immunol., 77 (2013) 431–441.
N.E. Ustyuzhanina, N.A. Ushakova, K.A. Zyuzina, M.I. Bilan, A.L. Elizarova, O.V. Somonova, A.V. Madzhuga, V.B. Krylov, M.E. Preobrazhenskaya, A.I. Usov,M.V. Kiselevskiy, N.E. Nifantiev “Influence of Fucoidans on Hemostatic System”, Mar. Drugs, 11 (2013) 2444-2458.
M.I. Bilan, A.A. Grachev, A.S. Shashkov, Thanh Thi Thu Thuy, Tran Thi Thanh Van, Bui Minh Ly, N.E. Nifantiev, A.I. Usov « Preliminary investigation of a highly sulfated galactofucan fraction isolated from the brown alga Sargassum polycystum», Carbohydr. Res. 377 (2013) 48-57.
E. Paulovičová, L. Paulovičová, R. Pilišiova, S. Bystricky, D.V. Yashunsky, A.A. Karelin, Y.E. Tsvetkov, and N.E. Nifantiev « Synthetically prepared glycooligosaccharides mimicking Candida albicans cell wall glycan antigens — novel tools to study host-pathogen interactions», FEMS Yeast Res., 13 (2013) 659–673.
2012
Y.E. Tsvetkov, M. Burg-Roderfeld, G. Loers, A. Arda, E.V. Sukhova, E.A. Khatuntseva, A.A. Grachev, A.O. Chizhov, H.-C. Siebert, M. Schachner, J. Jimenez-Barbero, N.E. Nifantiev, «Synthesis and Molecular Recognition Studies of the HNK-1 Trisaccharide and Related Oligosaccharides. The Specificity of Monoclonal Anti-HNK-1 Antibodies as Assessed by Surface Plasmon Resonance and STD NMR», J. Amer. Chem. Soc. 134 (2012) 426-435.
M. K. Sethi, F. F.R. Buettner, A. Ashikov, V. B. Krylov, H. Takeuchi, N. E. Nifantiev, R. S. Haltiwanger, R. Gerardy-Schahn and H. Bakker, «Molecular Cloning of a Xylosyltransferase that Transfers the Second Xylose to O-Glucosylated Epidermal Growth Factor Repeats of Notch”, J. Biol. Chem. 287 (2012) 2739-2748.
A.G. Gerbst, A.A. Grachev, A.S. Shashkov, N.E. Nifantiev, «Quantum mechanical calculation of 13C NMR chemical shifts in a series of isomeric fucobiosides with the account for conformational equilibrium», J. Carbohydr. Chem., 31 (2012) 93-104.
T. Eckert, S. Stötzel, M. Burg-Roderfeld, J. Sewing, T. Lütteke, N.E. Nifantiev, J.F.G. Vliegenthart, H.-C. Siebert, «In silico study on sulfated and non-sulfated carbohydrate chains from proteoglycans in Cnidaria and their interaction with collagen», Open J. Phys. Chem., 2 (2012) 123-133. doi:10.4236/ojpc.2012.22017
E.A. Khatuntseva, V.M. Men’shov, A.S. Shashkov, Y.E. Tsvetkov, R.N. Stepanenko, R.Y. Vlasenko, E.E. Shults, G.A. Tolstikov, T.G. Tolstikova, D.S. Baev, V.A. Kaledin, N.A. Popova, V.P. Nikolin, P.P. Laktionov, A.V. Cherepanova, T.V. Kulakovskaya, E.V. Kulakovskaya and N.E. Nifantiev, «Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel», Beilstein J. Org. Chem. 2012, 8, 763–775.
C. Pozzi, K. Wilk, J. C. Lee, M. Gening, N. Nifantiev, and G. B. Pier “Opsonic and Protective Properties of Antibodies Raised to Conjugate Vaccines Targeting Six Staphylococcus aureus antigens” PLoS ONE, 2012, 7(10): e46648. doi:10.1371/journal.pone.0046648
B. S. Komarova, Y. E. Tsvetkov, G. B. Pier, and N. E. Nifantiev “Synthesis of pentasaccharides corresponding to the glycoform II of the outer core region of Pseudomonas aeruginosa lipopolysaccharide” Carbohydr. Res. 360 (2012) 56-68.
L. Paulovičová, E. Paulovičová, A. A. Karelin, Yu. E. Tsvetkov, N. E. Nifantiev, S. Bystrický, “Humoral and cell-mediated immunity following vaccination with synthetic Candida cell wall mannan derived heptamannoside–protein conjugate. Immunomodulatory properties of heptamannoside–BSA conjugate” Internl. Immunopharmacol. 14 (2012) 179-187.
M.L. Gening, Y.E. Tsvetkov, D.V. Titov, A.G. Gerbst, O.N. Yudina, A.A. Grachev, A.S. Shashkov, S. Vidal, A. Imberty,T. Saha, D. Kand, P. Talukdar, G.B. Pier, and N.E. Nifantiev, “Linear and cyclic oligo-β-(1→6)-D-glucosamines: synthesis, conformations and applications for design of a vaccine and oligodentate glycoconjugates”, PureAppl. Chem., 84 (2012) in press.
D.V. Titov, M.L. Gening, A.G. Gerbst, A.O. Chizhov, Y.E. Tsvetkov, and N.E. Nifantiev “Stereochemistry of intramolecular cyclization of tetra-b-(1®6)-D-glucosamines and related tetrasaccharides: the role of the conformational stereocontrol and the neighboring group participation”, Carbohydr. Res. (2012) in press.
B.S. Komarova, S.S. Maryasina, Y.E. Tsvetkov, and N. E. Nifantiev, “Water-dependent reduction of carbohydrate azides by dithiothreitol“ SYNTHESIS., (2012), in press.
B.S. Komarova, N.E. Ustyuzhanina, Y.E. Tsvetkov, and N.E. Nifantiev, “Stereocontrol of 1,2-cis-Glycosylation by Remote O-Acyl Protecting Groups”, in S. Vidal and D. Wertz ed. “Modern Synthetic Methods in Carbohydrate Chemistry – From Monosaccharides to Complex Glycoconjugates”, Wiley, (2012) in press.
2011
D.O. Croci, A. Cumashi, N.A. Ushakova, M.E. Preobrazhenskaya, A. Piccoli, L. Totani, N.E. Ustyuzhanina, M.I. Bilan, A.I. Usov, A.A. Grachev, G.E. Morozevich, A.E. Berman, C.J. Sanderson, M. Kelly, P. Di Gregorio, C. Rossi, N. Tinari, S. Iacobelli, G.A. Rabinovich, N.E. Nifantiev “Fucans, but not fucomannoglucuronans, determine the biological activities of sulfated polysaccharides from Laminaria saccharina brown seaweed” PLoS ONE 2011, 6(2): e17283. doi:10.1371/journal.pone.0017283.
V. B. Krylov, Z.M. Kaskova, D. Z. Vinnitskiy, N.E. Ustyuzhanina, A.A. Grachev, A.O. Chizhov, N.E. Nifantiev “Acid-promoted synthesis of per-O-sulfated fucooligosaccharides related to fucoidan fragments”, Carbohydr. Res. 346 (2011) 540-550.
O.N. Yudina, M.L. Gening, Y.E. Tsvetkov, A.A. Grachev, G.B. Pier, and N.E. Nifantiev “Synthesis of five nona-β-(1→6)-D-glucosamines with various pattern of N-acetylation corresponding to the fragments of exopolysaccharide of Staphylococcus aureus” Carbohydr. Res. 346 (2011) 905-913.
A.A. Grachev, A.G. Gerbst, M.L. Gening, D.V. Titov, O.N. Yudina, Y.E. Tsvetkov, A.S. Shashkov, G.B. Pier, and N.E. Nifantiev “NMR and Conformational Studies of Linear and Cyclic Oligo-(1→6)-β-D-Glucosamines” Carbohydr. Res. 346 (2011) 2499-2510.
S.E. Semenov, S.L. Ioffe, N.E. Nifantiev “Moscow Chemical Lyceum”, Chem. Int., 33 (2011) 28-29.
2010
M.L. Gening, T. Maira-Litran,A. Kropec, D. Skurnik, M. Grout, Y.E. Tsvetkov, N.E. Nifantiev, G.B. Pier «Synthetic β(1→6)-linked N-acetylated and non-acetylated oligoglucosamines used to produce conjugate vaccines for bacterial pathogens» Infect. Immun., 78 (2010) 764-772 ( SPOTLIGHT: Articles of Significant Interest, page 567).
A. Bhunia, S. Vivekanandan, T. Eckert, M Burg-Roderfeld, R. Wechselberger, J. Romanuka, D. Bächle, A.V. Kornilov, C.-W. von der Lieth, J.J. Barbero, N. Nifantiev, M. Schachner, N. Sewald, T. Lütteke, H.-J. Gabius, H.-C. Siebert “Why structurally different cyclic peptides can be glycomimetics of the HNK-1 carbohydrate antigen”, J. Amer. Chem. Soc. 132 (2010) 96-105.
M.K. Sethi, F.F. R. Buettner, V. Krylov, H. Takeuchi, N. Nifantiev, R.S. Haltiwanger, R. Gerardy-Schahn, and H. Bakker «Identification of Glycosyltransferase 8 Family Members as Xylosyltransferases Acting on O-Glucosylated Notch Epidermal Growth Factor Repeats» J. Biol. Chem. 285 (2010) 1582-1586. http://www.jbc.org/content/current — content-block#content-blockAccelerated Publication
T.V. Kulakovskaya, W.I. Golubev, M.A. Tomashevskaya, E.V. Kulakovskaya, A.S. Shashkov, А.А. Grachev, and N.E. Nifantiev “Production of Antifungal Cellobiose Lipids by Trichosporon porosum”, Mycopathologia, 169 (2010) 117-123.
L. Paulovičová, S. Bystrický, E. Paulovičová, A.A. Karelin, Y.E. Tsvetkov, and N.E. Nifantiev “Model α-mannoside Conjugates — Immunogenicity and opsonopharocytic killing of Candida albicans .” FEMS Immunol. Med. Microbiol. 58 (2010) 307-313.
A.A. Karelin, Y.E. Tsvetkov, L. Paulovičová, S. Bystrický, E. Paulovičová, and N.E. Nifantiev “Synthesis of 3,6-branched oligomannoside fragments of the mannan from Candida albicans cell wall corresponding to the antigenic factor 4”, Carbohydr. Res. 345 (2010) 1283-1290.
H.-C. Siebert, L. Poppe, N.E. Nifantiev, Obituary: Janusz Dabrowski 1927–2009, Glycoconj. J., 27 (2010) 199-200.
M.L. Gening, D.V. Titov, A.A. Grachev, A.G. Gerbst, O.N. Yudina, A.O. Chizhov, Y.E. Tsvetkov, and N.E. Nifantiev “Synthesis, NMR and Conformational Studies of Cyclic Oligo-(1→6)-β-D-Glucosamines” Eur. J. Org. Chem. 13 (2010), 2465-2475. Статье посвящена обложка журнала: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201090031/pdf
A.G. Gerbst, A.A. Grachev, A.A. Vyboichtchik, A.S. Shashkov, A.I. Usov, N.E. Ustuzhanina, and N.E. Nifantiev, “Application of artificial neural networks for analysis of 13C NMR spectra of fucoidans”,J. Carbohydr. Chem. 29 (2010) 92-102.
M.I. Bilan, Alexey A. Grachev, A.S. Shashkov, M. Kelly, C.J. Sanderson, N. E. Nifantiev, A.I. Usov “Further studies on the composition and structure of a fucoidan preparation from the brown alga Saccharina latissima”, Carbohydr. Res., 345 (2010) 2038-2047.
