Department of Chemistry
Research in the Hili group is inspired by nature and operates at the interface of chemistry and biology. Our efforts rely upon expertise in synthetic organic chemistry, biochemistry, and molecular biology to mimic the approaches nature uses to solve complex problems with simple solutions. Our approach to science requires a diverse background of researchers from various scientific disciplines, generating a collaborative atmosphere for students, while garnering an expanded knowledge of the biological and chemical sciences. Our inspiration from nature is the use of DNA as a central blueprint, be it in the form of an information carrier, a molecular scaffold, or a functional polymer. In the Hili Group, the molecules that we study are always covalently linked to the DNA that encode their structure (I.e. phenotype is linked to genotype). By harnessing the power of in vitro selection, coupled with the high-throughput DNA sequencing facilities here at UGA, we can rapidly analyze, en masse, libraries containing millions of different molecules and identify those with desired properties (E.g. molecular recognition or catalysis). We plan to apply the technologies that we develop toward areas within organic synthesis and chemical biology, including small molecule catalyst discovery, aptamer and antibody mimetics development, and cell surface profiling.
Yudin, A. K.; Hili, R. 2012 “Aziridine Aldehydes, Aziridine-Conjugated Amino Derivatives, Aziridine- Conjugated Biomolecules and Processes for their Preparation” U.S. Patent 8,143,375, filed 22 October 2007, and issued 27 March 2012.
Yudin, A. K.; Rai, V.; Hili, R. 2011 “A Method to Insert Molecular Fragments into Cyclic Molecules” CA2011/000630, filed 31 May 2011, patent pending.
Yudin, A. K.; Hili, R. 2010 “Preparation of Aziridine-Conjugated Cyclic Amino Acid Derivatives” US 2012/0065366 A1, filed 16 March 2010, patent pending.
Niu, J.; Hili, R.; Liu, D. R. “Enzyme-Free Translation of DNA into Sequence-Defined Synthetic Polymers Structurally Unrelated to Nucleic Acids” Nature Chemistry, 2013, 5, 282-292.
Hili, R.; Niu, J.; Liu, D. R. “DNA Ligase-Mediated Translation of DNA Into Densely Functionalized Nucleic Acid Polymers” J. Am. Chem. Soc, 2013, 135, 98—101.
Zaretsky, S; Rai, V.; Rotstein, B. H.; Hili, R.; Ler, S.; Scully, C. C. G.; St. Denis, J. D.; Yudin, A. K. “Peptide Cyclization Enabled by Aziridine Aldehyde Dimers: Mechanistic Aspects and Process Development”Submitted, 2013.
Assem, N.; Hili, R.; He, Z.; Kasahara, T.; Inman, B.; Decker, S.; Yudin, A. K. “The Role of Reversible Dimerization in Reactions of Amphoteric Aziridine Aldehydes” J. Org. Chem., 2012, 77, 5613—5623.
Rotstein, B. H.; Rai, V.; Hili, R.; Yudin, A. K. “Synthesis of Peptide Macrocycles Using Unprotected Amino Aldehydes” Nature Protocols, 2010, 5, 1813—1822.
Jebrail, M. J.; Ng, A. H. C.; Rai, V.; Hili, R.; Yudin, A. K.; Wheeler, A. “Synchronized Synthesis of Peptide-Based Macrocycles by Digital microfluidics“ Angew. Chem. Int. Ed. 2010, 49, 8625—8629.
Hili, R.; Rai, V.; Yudin, A. K. “Macrocyclization of Linear Peptides Enabled by Amphoteric Molecules” J. Am. Chem. Soc. 2010, 132, 2889—2891.
Hili, R.; Yudin, A. K. “Amphoteric Amino Aldehydes Reroute the Aza-Michael Reaction” J. Am. Chem. Soc.,2009, 131, 16404—16406.
Baktharaman, S.; Hili, R.; Yudin, A. K. “Amino Carbonyl Compounds in Organic Synthesis’’ Aldrichimica Acta,2008, 41, 109—119.
Hili, R.; Baktharaman, S.; Yudin, A. K. “Synthesis of Chiral Amines Using a-amino aldehydes” Eur. J. Org. Chem. 2008, 31, 5201—5213.
Hili, R.; Yudin, A. K. “Amphoteric Amino Aldehydes Enable Rapid Assembly of Unprotected Amino Alcohols”Angew. Chem. Int Ed. 2008, 47, 4188—4191
Yudin, A. K., Hili, R. “Overcoming the Demons of Protecting Groups with Amphoteric Molecules” Chem. Eur. J. 2007, 13, 6538—6542.
Hili, R.; Yudin, A. K. “Readily Available Unprotected Amino Aldehydes” J. Am. Chem. Soc. 2006, 128, 14772—14773.
Hili, R., Yudin, A. K. “Making Carbon-Nitrogen Bonds in Biological and Chemical Synthesis” Nature Chem. Biol. 2006, 2, 284—287.
Krasnova, L.B.; Hili, R.; Chernoloz, O.V.; Yudin, A.K. “Phenyliodine(III) Diacetate as a Mild Oxidant for Aziridination of Olefins and Imination of Sulfoxides with N-aminophthalimide” Arkivoc 2005, 4, 26—38.