FACULTY & STAFF
Rajesh Viswanathan
Assistant Professor
Synthetic Organic Chemistry and Chemical Biology
214 Millis Science Bldg.
Phone: 216.368.3696
E-mail: rajesh.viswanathan [at] case [dot] edu
B. Sc., Madras University, India, 1997
M. Sc., Indian Institute of Technology, Kanpur, India, 1999
Ph. D. Indiana University, Bloomington, 2005
NIH Post-Doctoral Research Fellow, University of Utah
Research Interests
Syntheses of Oxindole-Terpenoid Scaffold – Studies Towards Biosynthetic Pathway Elucidation
Welwitindolinone C isothiocyanate belongs to a family of structurally unique indole alkaloids isolated from the blue-green alga Hapalosiphon welwitschii. Several other cyanobacterial sources have been reported to biosynthesize these alkaloids: Hapalosiphon delicatulus, Hapalosiphon hibernicus, Fischerella ambigua, Fischerella muscicola to name a few. This set of terpenoid-indole alkaloids provides an inspiring and challenging area for research. Currently, the biosynthetic pathways operating in cyanobacteria leading to this family of alkaloids is poorly understood. The terpenoid core of fischerindole and welwistatin are presumably arising from the hapalindole core. A biomimetic synthetic approach towards the six membered mono-terpene ring will be pursued. Success in this direction will not only aid the preparation of precursors for biosynthesis studies but also yield a concise synthetic approach toward halogenated terpenoid natural products.
Site Selective Modifications of Proteins for Microarray Platforms
Microarrays have become a standard technique to probe protein-protein, protein-antibody and protein-small molecule interactions. Uniform spatial immobilization of a protein or an enzyme in its native fold through site specific tethering will result in a robust and reliable microarray that performs superiorly than arrays consisting of randomly oriented biomolecules. Our group is interested in developing new Chemical Biology tools toward site-selective modifications of proteins.
- Labadie G. R.; Viswanathan R.; Poulter C. D. “Farnesyl Diphosphate Analogues with ω-Bioorthogonal Azide and Alkyne Functional Groups for PFTase-Catalyzed Ligation Reactions”, J. Org. Chem. 2007, 72, 9291-9297.
- Viswanathan R.; Smith C. R.; Prabhakaran E. N.; Johnston J. N. “Free Radical-Mediated Aryl Amination: Convergent Two- and Three-Component Couplings to Chiral 2, 3-Disubstituted Indolines”, J. Org. Chem. 2008, 73, 3040-3046.
- Srinivasan, J. M.; Burks, H. E.; Smith, C. R.; Viswanathan, R.; Johnston, J. N. “Free Radical-Mediated Aryl Amination: A Practical Synthesis of (R)- and (S)-7-Azaindoline α-Amino Acid”, Synthesis (Practical Synthetic Procedures) 2005, 2, 330-333.
- Viswanathan, R.; Mutnick, D.; Johnston J. N. “The First Azacyclopentenyl Carbinyl Radical Isomerizations (ACCRI): Independent Use of Steric and Electronic (Polarization) Effects as Gating Elements”, J. Am. Chem. Soc. 2003, 125, 7266-7271.
- Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. “Free Radical-Mediated Aryl Amination and its Use in a Convergent [3+2] Strategy for Enantioselective Indoline α-Amino Acid Synthesis”, J. Am. Chem. Soc. 2003, 125, 163-168.
- Johnston, J. N.; Plotkin, M. A.; Viswanathan, R.; Prabhakaran, E. N. “Nonconventional Carbon Additions to Azomethines. Aryl Amination/Indoline Synthesis by Direct Aryl Radical Addition to Azomethine Nitrogen”, Org. Lett. 2001, 3, 1009–1011.
- Mullins R. J.; Vedernikov A.; Viswanathan R. “Competition Experiments as a Means of Evaluating Linear Free Energy Relationships”, J. Chem. Ed. 2004, 81, 1357-1361.