Alexei V. Demchenko
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 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.
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. 2008, 73, 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, 2008, 133, 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, 2008, 73, 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.