Chemistry and Biochemistry

Alexei V. Demchenko

 

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Professor Demchenko received his M. Sc. in Chemical Engineering from D. I. Mendeleyev University of Chemical Technology of Russia, Moscow (1988) and received his Ph. D. in Organic Chemistry from N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow (1993). He was a BBSRC post-doctoral research fellow at School of Chemistry, University of Birmingham, United Kingdom and a research assistant at the Complex Carbohydrate Research Center, University of Georgia, Athens before joining the UM-St. Louis faculty in 2001. Professor Demchenko was appointed Curators' Professor of Chemistry and Biochemistry in 2014..

Research Interests

Novel glycosylation reactions, methods and approaches. Stereocontrol and other aspects of 1,2-cis-glycosidic bond formation. β-Mannosylation.

New methods and approaches to the complementary synthesis of 1,2-trans-glycosidic bond. Base-stable arming participating groups.

Thioimidates as glycosyl donors for stereoselective glycosylation and versatile building blocks for convergent oligosaccharide synthesis.

Highly efficient strategies for the synthesis of complex oligosaccharides and glycoconjugates: selectivity, chemoselectivity, and orthogonality of modern glycosyl donors.

Transition metal complexes in synthetic carbohydrate chemistry: direction of the stereoselectivity of glycosylation, temporary deactivation, etc.

Regioselective protection of carbohydrate molecules. Design and application of modern protecting groups and strategies to the synthesis of versatile building blocks.\

Fully synthetic therapeutics based on oligosaccharides with potential biological activity (HIV, anti-cancer, anti-inflammatory, antibiotics, antiviral, antifungal, etc.). Synthetic glycoproteins, glycopeptides, glycopolymers, glycolipids, glycoheterocycles, and glycodendrimers.

Glycosphingolipids and other biologically important sialic acid containing glycoconjugates. Structurally modified neuraminic acid derivatives: chemo-enzymatic synthesis, derivatization, chemical and enzymatic sialylation.

Solid phase and surface chemistry: application to stereoselective glycosylation and rapid assembly of complex oligosaccharides and glycopeptides. Combinatorial chemistry.

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Selected Publications

″Hydrogen bond mediated aglycone delivery: Synthesis of linear and branched α-glucans″, J. P. Yasomanee and A. V. Demchenko, Angew Chem. Intl Ed. 2014 (n press).

″Glycosyl alkoxythioimidates as building blocks for glycosylation: a reactivity study″ S. C. Ranade and A. V. Demchenko, Carbohydrate Res. 2014 (in press).

"2-acylamido analogues of n-acetylglucosamine prime formation of chitin oligosaccharides by yeast chitin synthase 2,"J. Gyore, A. R. Parameswar, C. F. F. Hebbard, Y. Oh, E. Bi, A. V. Demchenko, N. P. Price and P. Orlean, J. Biol. Chem. 2014, 289, 12835

"Hydrogen-bond-mediated aglycone delivery: Focus on β-mannosylation,"  S. G. Pistorio, J. P. Yasomanee and A. V. Demchenko," Org. Lett. 2014, 16, 716

“Regenerative Glycosylation under Nucleophilic Catalysis”, S. S. Nigudkar, K. J. Stine and  A. V. Demchenko, J. Am. Chem. Soc., 2014, 126, 921.

"Square-wave voltammetry assays for glycoproteins on nanoporous gold," B. Pandey, J. K. Bhattarai, P. Pornsuriyasak, K. Fujikawa,R. Catania, A. V. Demchenko and K. J. Stine, J. Electroanal. Chem. 2014, 717/718, 47.

"A Comparative Study of Glycosyl Thioimidates as Building Blocks for Chemical Glycosylation," S. C. Ranade, S. J. Hasty and A. V. Demchenko, J. Carbohydrate Chem. 2013, 32, 360.

 "Super-Arming of Glycosyl Donors by Combined Neighboring and Conformational Effects.," M. Heuckendorff, H. D. Premathilake, P. Pornsuriyasak, A. O. Madsen, C. M. Pedersen, M. Bols and A. V. Demchenko, Org. Lett. 2013, 15 4904

 "Reactive thiogluciside-substrates for b-glucosidase," A. E. Alverson-Banks, S. J. Hasty, A. R. Parameswar, G. S. Howarth, A. V. Demchenko and L. D. Byers, Arch. Biochem. Biophys. 2013, 537, 1

"Surface-Tethered Iterative Carbohydrate Synthesis: A Spacer Study," V. N. Ganesh, K. Fujikawa, Y-H. Tan, S. S. Nigudkar, K. J. Stine and A. V. Demchenko, J. Org. Chem. 2013, 78, 6849.

“O-Benzoxazolyl imidates as versatile glycosyl donors for chemical glycosylation”, Swati S. Nigudkar, Archana R. Parameswar, Papapida Pornsuriyasak, K. J. Stine, and A.i V. Demchenko, Org. and Biomol. Chem., 2013, 11, 4068.

“Lectin-Carbohydrate Interactions on Nanoporous Gold Monoliths”, Y.-H. Tan, K. Fujikawa, P. Pornsuriyasak, A. J. Alla, A. V. Demchenko and K. J. Stine, New J. Chem., 2013, 37, 2150.

"Mechanism of Chemical Glycosylation: focus on the Node of Activation and Departure from Anomeric Leaving Groups," S. C. Ranade and A. V. Demchenko,  J. Carbohydrate Chem2013, 32, 1.

"Effect of Remote Picolinyl and Picolyl Substituents on the Stereoselectivity of Chemical Glycosylation. J. P.  Yasomanee and A. V. Demchenko, J. Am. Chem. Soc. 2012, 134, 20097.

“Electrochemical Characterization of Globotriose-Containing Self-Assembled Monolayers on Nanoporous Gold and their Binding of Soybean Agglutinin”, B. Pandey, Y. H. Tan,  A. R. Parameswar, P. Pornsuriyasak, A. V. Demchenko and K.  J. Stine, Carbohydrate Research, 2012, 373, 9.