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Alexei V. Demchenko

Alexei V. DemchenkoProfessor 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 is a recipient of the CAREER Award from the National Science Foundation (2005) and the New Investigator Award from the carbohydrate division of the American Chemical Society (2007).

demchenkoa@umsl.edu
Fax:       (314) 516-5342
Office:   B434
Phone:  (314) 516-7995

Glycoworld (Alexei Demchenko Laboratory Homepage)

Research Interests

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

"STICS: surface-tethered iterative carbohydrate synthesis"  P.  Pornsuriyasak, S. C. Ranade, A.Li, C. M. Parlato, C. R. Sims, O. V. Shulga, K. J. Stine and A. V. Demchenko, Chemical Commun. 2009, 1834

"Unexpected Orthogonality of S-Benzoxazolyl and S-Thiazolinyl Glycosides: Application to Expeditious Oligosaccharide Assembly" S. Kaeothip, P. Pornsuriyasak, N. P. Rath and A. V. Demchenko, Organic Letters, 2009, 11, 799

"4-(Pyridin-2-yl)thiazol-2-yl thioglycosides as bidentate ligands for oligosaccharide synthesis via temporary deactivation" P. Pornsuriyasak, N. P. Rath and A. V. Demchenko,  Chem. Commun. 2008, 5633

"How the Arming Participating Moieties can Broaden the Scope of Chemoselective Oligosaccharide Synthesis by Allowing the Inverse Armed-Disarmed Approach" J. T. Smoot and A. V. Demchenko,  J. Org. Chem. 200873,  8838

"Synthesis of spacer-containing analogs of sero-group 6 pneumococcal oligosaccharides". A. R. Parameswar, S. J. Hasty and A. V. Demchenko, Carbohydrate Res. 2008, 343, 1707

"Superarming the S-Benzoxazolyl Glycosyl Donors by Simple 2-O-Benzoyl-3,4,6-tri-O-benzyl Protection". L. K. Mydock and A. V. Demchenko, Org. Lett. 2008, 10, 2103

"Application of the Superarmed Glycosyl Donor to Chemoselective Oligosaccharide Synthesis". L. K. Mydock and A. V. Demchenko, Org. Lett. 2008, 10, 2107

"Silver(I) tetrafluoroborate as a potent promoter for chemical glycosylation". S. Kaeothip, P. Pornsuriyasak and A. V. Demchenko, Tetrahedron Letters, 2008, 49, 1542.

"Detection of free prostate specific antigen (fPSA) on a nanoporous gold platform". O. V. Shulga, D. Zhou, A. V. Demchenko and K. J. Stine, Analyst, 2008133, 319.

"Application of Glycosyl Thioimidates in Solid-Phase Oligosaccharide Synthesis". M. C.  Parlato, M. Kamat, H. Wang, K. J. Stine and A. V. Demchenko,  Journal of Organic Chemistry, 200873, 1716.

"Thermophysical properties in medium temperature range of several thio and dithiocarbamates". M.  Temprado, M. V. Roux, A. R. Parameswar, A. V. Demchenko, J. S. Chickos and J. F. Liebman,   Journal of Thermal Analysis and Calorimetry, 2008, 91, 471.

"S-Benzoxazolyl as a stable protecting moiety and a potent anomeric leaving group in oligosaccharide synthesis". M. N. Kamat, C. De Meo and A. V. Demchenko. J. Org. Chem. 2007, 72, 6947.

"Versatile synthesis and mechanism of activation of S-benzoxazolyl glycosides". M. N. Kamat, N. P. Rath and A. V. Demchenko. J. Org. Chem. 2007, 72, 6938.

"S-Benzoxazolyl (SBox) approach to the synthesis of glycosides of 2-deoxy-2-aminosugars. A. F. G. Bongat, M. N. Kamat, A. V. Demchenko". J. Org. Chem., 2007, 72, 1480.

"S-Thiazolinyl (STaz) glycosides as versatile building blocks for convergent selective, chemoselective, and orthogonal oligosaccharide synthesis". P. Pornsuriyasak and A. V. Demchenko. Chem. Eur. J., 2006, 12, 6630.