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Alexei V. Demchenko

Demchenko pic 2016

Professor Demchenko received his M. Sc. in Chemical Engineering from the D. I. Mendeleyev University of Chemical Technology of Russia, Moscow (1988) and  his Ph. D. in Organic Chemistry from the N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow (1993). He was a post-doctoral fellow at the University of Birmingham, (UK) and a research assistant at the Complex Carbohydrate Research Center at the University of Georgia before joining the UMSL faculty in 2001. He was appointed Curators' Professor of Chemistry and Biochemistry in 2014. Fax: (314) 516-5342
Office:S 308d
Tel: (314) 516-7995

(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.

research areas:

Selected Publications

″Glycosyl nitrates in synthesis: streamlined access to glucopyranose building blocks differentiated at C-2,″ T. Wang, S. S. J. P. Yasomanee, N. P. Rath, Nigam K. J. Stine and A. V. Demchenko, Org. & Biomol. Chem. 2018, Ahead of Print

″Immobilization of glycans on solid surfaces for application in glycomics, ″ C. L. O'Neil, K. J  Stine and A. V. Demchenko, J. Carbohydrate Chem. 2018, Ahead of Print

″Preparation, modification, characterization, and biosensing application of nanoporous gold using electrochemical techniques″, J. K. Bhattarai, D. Neupane, B. Nepal, V. Mikhaylov, A. V. Demchenko and K. J. Stine, Nanomaterials, 2018, 8, 171/1

″Intramolecular glycosylation,″ X. G. Gia and A. V. Demchenko, Beilstein J. Org. Chem. 2017, 13, 2028.

″Regenerative Glycosylation,″ Y. Singh, T. Wang, S. A. Geringer, K. J. Stine and A. V. Demchenko, J. Org. Chem. 2018, 83, 374.

″Conformationally super-armed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot,″ M. D. Bandara, J. P. Yasomanee, N. P. Rath, C. M. Pedersen, M. Bols and A. V. Demchenko, Org. & Biomol. Chem. 2017, 15, 559.

″Extending the S-benzimidazolyl (SBiz) platform: N-alkylated SBiz glycosyl donors with the universal activation profile,″  S. J. Hasty, N. P. Rath and A. V. Demchenko, Pure Appl. Chem. 2017, 89, 1321

″Intramolecular glycosylation,″ X. G. Jia and A. V. Demchenko, Beilstein J. Org. Chem., 2017, 13, 2028

″S-Benzimidazolyl (SBiz) Imidates as a Platform for Oligosaccharide Synthesis via Active-Latent, Armed-Disarmed, Selective, and Orthogonal Activations,″ S. J. Hasty, M. D. Bandara, N. P. Rath and A. V. Demchenko, J. Org. Chem. 2017, 82, 1904.

″OFox imidates as versatile glycosyl donors for chemical glycosylation,″ S. S. Nigudkar, T. Wang, S. G. Pistorio, J. P. Yasomanee, K. J. Stine and A. V. Demchenko, Org. & Biomol. Chem. 2017, 15, 348.

Templated Oligosaccharide Synthesis: Driving Forces and Mechanistic Aspects,″ X. G. Ziao, P. Pornsuriyasak and A. V. Demchenko, J. Org. Chem. 2016, 81, 12232.

″The synthesis of the repeating unit of capsular polysaccharide Staphylococcus aureus type 5 to study chemical activation and conjugation of native CP5,″ J. P. Yasomanee, S. Visansirikul, P. Pornsuriyasak, M. Thompson, S. A. Kolodziej and A. V. Demchenko, J. Org. Chem. 2016, 81, 5981.

″Templated Oligosaccharide Synthesis: The Linker Effect on the Stereoselectivity of Glycosylation,″ P. Pornsuriyasak, Papapida; X. G. Jia, S. Kaeothip and A. V. Demchenko, Org. Lett. 2016, 18, 2316.

″2,3-Di-O-picolinyl building blocks as glycosyl donors with switchable stereoselectivity,″ J. P. Yasomanee, A. R. Parameswar, P. Pornsuriyasak, N. P. Rath and A. V. Demchenko, Org. & Biomol. Chem. 2016, 14, 3159.

″Hydrogen-Bonded Mediated Aglycone Delivery (HAD): A highly Stereoselective Synthesis of 1,2-cis-a-D-Glucosides from Common Glycoside Donors,″ J. Yasomanee and A. V.  Demchenko, Chem.  A Eur. J. 2015, 21, 6572.