Chemistry and Biochemistry

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. 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.

Figure 2

Selected Publications

"HPLC-Assisted Automated Oligosaccharide Synthesis," N. V. Ganesh, K. Fujikawa, Y-H. Tan, K. J. Stine and A. V. Demchenko, Org. Lett.  2012, 14, 3036.

"2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis," H. D. Premathilake and A. V. Demchenko, Beilstein J. Org. Chem. 2012, 8, 597 (No. 66).

"Surface Area and Pore Size Characteristics of Nanoporous Gold Subjected to Thermal, Mechanical, or Chemical Modifications studied using BET Isotherm Analysis, Cyclic Voltammetry, and Scanning Electron Microscopy”, Y-H. Tan, J. A. Davis, K. Fujikawa, N. V. Ganesh, A. V. Demchenko and K. J. Stine, J. Mat. Chem., 2012, 22, 6733.

"How O-Substitution of Sialyl Donors Affects Their Stereoselectivity," H. D. Premathilake, C. P. Gobble, P; Pornsuriyasak, T. Hardimon, A. V. Demchenko, and C. De Meo, Org. Lett. 2012, 14, 1126. 

"Synthesis of Thioglycosides and thioimidates from peracetates," A. R. Parameswar, A. Imamura and A. V. Demchenko, Carbohydrate Chem: Proven Synth. Meth. 2012, 1, 187. 

"Synthesis of Thioglycosides and thioimidates from glycosyl halides," A. R. Parameswar, D. Mueller, L. Liu,C. De Meo and A. V. Demchenko, Carbohydrate Chem: Proven Synth. Meth. 2012, 1, 181. 

"Glycosidation of Thioglucosides in the Ptresence of Bromine: Mechanism, reactivity and Stereoselectivity," S. Kaeothip, J. P. Yasomanee and A. V. Demchenko, J. Org. Chem. 2012, 77, 291.

"In vivo imaging of epileptic activity using 2-NBDG, a fluorescent deoxyglucose analog," V. Tsytsarev, K. I Maslov, J. Yao, A. R. Parameswar, A. V. Demchenko and L. V. Wang, J. Neuroscience Meth. 2012, 203, 136.  

“Development of LPS antagonistic therapeutics: synthesis and evaluation of glucopyranoside-spacer-amino acid motifs”, S. Kaeothip, G. Paranjape, S. E. Terrill, A. F. G. Bongat, M. L. D. Udan, T. Kamkhachorn, H. L. Johnson, M. R. Nichols and A. V. Demchenko, RSC Advances, 2011, 1, 83.

"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.

"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.