Organic Synthesis: Chiral synthons (chirons) derived from natural amino acids and sugars are employed in the synthesis of unusual amino acids, carbohydrate derivatives and natural products. Asymmteric transformations of these chirons provide an opportunity to target molecules containing multiple and contiguous stereogeniccentres. We use asymmetric organocatalytic reactions such as proline catalyzed α-amination and α-hydroxylation to synthesize highly functionalized targets in very high diastereo- and enantiopurity. Unusual amino acids in peptide design: The use of unusual amino acids in peptides to impart directed hydrogen bonding is an effective tool to get oligopeptides with desired secondary structures. Such structures can not only provide basic understanding of protein folding, but can also be used to synthesize peptides that may self-assemble and be used for drug delivery and related applications. We are involved in the synthesis and application of amino acids containing hydrogen bond donor and acceptor side chains that are designed to stabilize helices and turns in smaller peptides. Substituted proline derivatives are designed to enhance cis/trans peptide bonds and to stabilize specific turns in peptides containing them. The synthesis of C-linked organome-tallic and fluorescent amino acids for sensor applications is another area that we actively pursue. Peptide Conjugates: Functionalizing peptides with small molecules that are biologically active is an efficient method for generating molecules with the potential to be used in therapeutic and diagnostic applications. We are involved in the synthesis of peptides conjugated with nucleophilic molecules to be used for the reactivation of acetylcholine esterase, rendered inactive by exposure to organophosphorous compounds. Using a similar approach, we are also attempting to develop molecular sensors for organophosphorous and related chemical warfare agents. We are developing small molecule conjugates of peptides to be used for glycosidase inhibition and cancer chemotherapeutics.

• Unusual reactions of the 1,3-dithiane derivative of the garner aldehyde and related compounds, Synthesis, 45, 1997 (2013).

• Powerful binders for the D-dimer by conjugation of the GPRP peptide to polypeptides from a designed set-illustrating a general route to new binders for proteins, Bioconjugate Chem., 24, 17 (2013).

• Synthesis of γ-oxo γ-aryl and γ-aryl α-amino acids from aromatic aldehydes and serine, Eur. J. Org. Chem., 36, 7120 (2012).

• Mixed pentafluorophenyl and o-fluorophenyl esters of aliphatic dicarboxylic acids: efficient tools for peptide and protein conjugation, RSC Advances, 2, 908 (2012).

• Applications of propargyl esters of amino acids in solution-phase peptide synthesis, Int. J. Peptides, 854952 (2011).

• Powerful protein binders from designed polypeptides and small organic molecules-A general concept for protein recognition, Angew. Chem. Int. Ed. 50, 1823 (2011).

• An improved procedure for the synthesis of dehydroamino acids and dehydropeptides from the carbonate derivatives of serine and threonine using tetrabutylammonium fluoride, J. Pept. Sci. 16, 123 (2010).

• Propargyl Chloroformate. Encyclopedia of Reagents for Organic Synthesis, John Wiley and Sons. DOI: 10.1002/047084289X.rn00816

• Assistant Professor, Department of Chemistry, Indian Institute of Technology Kanpur, 2010-.

• Uppsala University, Postdoctoral researcher, 2007-2010

Office

SL 207,
Department of Chemistry
IIT Kanpur,
Kanpur 208016

Office Phone: 0512-259-6684 (O)

Email: rameshr[AT]iitk.ac.in