Ronald Breslow

MC 3105

work:+1 212-854-2170

fax:+1 212-854-2755

Breslow Research Group
Selected Publications

Research Summary

My research group is pursuing studies in several different areas. In our major effort we are trying to prepare artificial enzymes that can imitate the function of natural enzymes. Students typically design a potential catalyst on the computer, synthesize it, then determine its catalytic effectiveness and the mechanism involved. One of the most interesting recent successes is the preparation of such enzyme mimics that carry out selective oxidations of bound substrates with geometric control of the position attacked. In this way we override the natural reactivities of the substrate by using the geometric control imposed by defined binding to the catalyst.

A related study involves the synthesis of mimics of antibodies or of biological receptor sites, constructing molecules that will bind to polypeptides with sequence selectivity in water, using mainly hydrophobic interactions. These could be very useful in modulating the activity of peptide hormones, for instance.

Reactions in water can be influenced by the hydrophobic effect. We are studying the use of this effect to promote and direct chemical reactions, and also to furnish information about the geometries of transition states. The results have been striking, furnishing information not available by other techniques.

We have had a long-standing program to develop novel compounds that can induce cells to differentiate. These have important potential in cancer treatment, and are now in human trials.

In our earliest work we extended the range of aromatic compounds, and synthesized other compounds that we showed to be antiaromatic. We are still pursuing studies on antiaromatic compounds, particularly those with triplet ground states that have potential applications in materials science.

Publications

Ronald Breslow and Frank Foss Jr., “Charge Transport in Nanoscale Aromatic and Antiaromatic Systems,” J. Phys.: Condens. Matter 20, 374104 (2008)

Mindy Levine, Craig S. Kenesky, Shengping Zheng, Jordan Quinn, and Ronald Breslow, “Synthesis and Catalytic Properties of Diverse Chiral Polyamines,” Tetrahedron Lett. 49, 5746-5750 (2008)

Mindy Levine, Daniel Mazori and Ronald Breslow, “Enantioselective Synthesis and Enantiomeric Amplification of Amino Acids under Prebiotic Conditions” Org. Lett., 10, 2433-2436 (2008)

Jordan R. Quinn, Frank W. Foss, Jr., Latha Venkataraman, and Ronald Breslow, “Oxidation Potentials Correlate with Conductivities of Aromatic Molecular Wires,” J. Am. Chem. Soc., 129, 12376-12377 (2007)

Ronald Breslow, “A Fifty-Year Perspective on Chemistry in Water,” Organic Reactions in Water, Marcus Lindstrom, ed., Blackwell Publishers, Oxford, pp. 1-28 (2007)

Jordan R. Quinn, Frank W. Foss, Jr., Latha Venkataraman, Mark S. Hybersten and Ronald Breslow, “Single-Molecule Junction Conductance through Diaminoacenes,” J. Am. Chem. Soc., 129, 6714-6715 (2007)

Ronald Breslow, Sujun Wei, and Craig Kenesky, “Enantioselective Transaminations by Dendrimeric Enzyme Mimics,”Tetrahedron, 63, 6317-6321 (2007)

Subhajit Bandyopadhyay, Wenjun Zhou and Ronald Breslow, “Isotactic Polyethylenimines Induce Formation of L-Amino Acids in Transamination,” Org. Lett. 9, 1009-1012 (2007)

Paul A. Marks and Ronald Breslow, “Dimethylsulphoxide to Vorinostat: Development of this Histone Deacetylase Inhibitor as an Anticancer Drug,” Nature Biotech. 25, 84-90 (2007)