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
"Reverse Orthogonal Strategy for Oligosaccharide Synthesis", K. Fujikawa, N. V. Ganesh, Y. H. Tan, K. J Stine and A. V. Demchenko, Chem. Commun. 2011, 10602
"Direct Synthesis of Diastereomerically Pure Glycosyl Sulfonium Salts", L. K. Mydock, M. N. Kamat and A. V. Demchenko, Organic Lett. 2011, 13, 2928
"Superarmed and superdisarmed building blocks in expeditious oligosaccharide syntheses", H. D. Premathilake and A. V. Demchenko, Topics in Current Chemistry, 2011, 301, 189.
"S-benzimidazolyl glycosides as a platform for oligosaccharide synthesis by an active-latent strategy", S. J. Hasty, M. A. Kleine and A. V. Demchenko, Angew. Chem., Int. Ed. (Eng), 2011, 50, 4197.
"Concise synthesis of 1,3-di-O-substituted tetrahydropyran derivatives as conformationally stable pyranose mimetics", L. K. Mydock, C. D. Spilling and A. V. Demchenko, Comptes Rendus Chim. 2011, 14, 301.
"Synthesis, characterization and reactivity of carbohydrate platinum(iv) complexes with thioglycoside ligands" C. Vetter, P. Pornsuriyasak, J. Schmidt, N. P. Rath, T. Rueffer, A. V. Demchenko and D. Steinborn, Dalton Trans 2010, 39, 6327
"Comparison of the Armed/Disarmed Building Blocks of the D-Gluco and D-Glucosamino Series in the Context of Chemoselective Oligosaccharide Synthesis", T. Kamkhachorn, A. R. Parameswar and A. V. Demchenko, Organic Letters 2010, 12, 3078.
"Concise Synthesis of the Unnatural Sphingosine and Psychosine Enantiomer", A. R. Parameswar, J. A. Hawkins, L. K. Mydock, M. S. Sands and A. V. Demchenko, Eur. J. Org. Chem. 2010, 3269.
"Experimental and Theoretical Study of the Structures and Enthalpies of Formation of 3H-1,3-Benzoxazole-2-thione, 3H-1,3-Benzothiazole-2-thione, and Their Tautomers", M. V. Roux, M. Temprado, P. Jimenez, C. Foces-Foces, R. Notario, A. R. Parameswar, A. V.; Demchenko, J. S. Chickos, C. A. Deakyne and J. F. Liebman, J. Phys. Chem. A, 2010, 114, 6336.
"Super-arming Common Glycosyl Donors by Simple 2-O-Benzoyl-3,4,6-tri-O-benzyl Protection", H. D. Premathilake, L. K. Mydock and A. V. Demchenko, J. Org. Chem. 2010, 75, 1095.
"Mechanism of chemical O-glycosylation: from early studies to recent discoveries", L. K. Mydock and A. V. Demchenko, Org. Biomolecular Chem. 2010, 8, 497
"Synthesis, Conjugation, and Immunological Evaluation of the Serogroup 6 Pneumococcal" Oligosaccharides. A. R. Parameswar, I. H. Park, R. Saksena, P. Kovac, M. H. Nahm and A. V. Demchenko, ChemBioChem 2009, 10, 2893.
"Coordination chemistry approach to the long-standing challenge of stereocontrolled chemical glycosylation", P. Pornsuriyasak, C. Vetter, S. Kaeothip, M. Kovermann, J. Balbach, D. Steinborn and A. V. Demchenko, Chem. Commun. 2009, 42, 6379.
"Identification of a simple chemical structure associated with protective human antibodies against multiple pneumococcal serogroups," S. Park, A. R. Parameswar, A. V. Demchenko, M. H. Nahm. Infect. Immun., 2009, 77, 3374.
"Oligosaccharide synthesis: from conventional methods to modern expeditious strategies," J. T. Smoot, A. V. Demchenko. Adv. Carbohydr. Chem. Biochem. 2009, 62, 161.