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Ronald Breslow

MC 3105

work:+1 212-854-2170

fax:+1 212-854-2755

rb33@columbia.edu

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.


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Publications
S. Schneebeli, M. Kamenetska, Z. Cheng, R. Skouta, R. A. Friesner, L. Venkataraman, and R. Breslow, “Single-Molecule Conductance through Multiple π−π-Stacked Benzene Rings Determined with Direct Electrode-to-Benzene Ring Connections” J. Am. Chem. Soc. 133, 2136–2139. (2011)

S. Schneebeli, M. Kamenetska, F. Foss, H. Vazquez, R. Skouta, M. Hybertsen, L. Venkataraman, and R. Breslow, “The Electrical Properties of Biphenylenes” Org. Lett. 12, 4114–4117. (2010)

Huanyu Zhao and Ronald Breslow, “A mimic of the pyruvate dehydrogenase complex.” Bioorg. Med. Chem. Lett. 20, 5973-5975. (2010)

R. Breslow, “Cyclodextrins,” in Molecular Encapsulation, Eds. Uso Berinker and Jean-Luc Mieusset, Wiley, Chichester UK, pp. 43-65. (2010)

R. Breslow, “The Principles and Reasons for Using Water as a Solvent for Green Chemistry,” in Green Solvents, Eds. Paul Anastas and Chao-Jun Li, Wiley-VCH, Weinheim Germany, pp.1-29. (2010)

Ronald Breslow and Zhan-Ling Cheng, “L-amino acids catalyze the formation of an excess of D-glyceraldehyde, and thus of other D sugars, under credible prebiotic conditions.”
 
Proc. Natl. Acad. Sci. USA. 107:5723-5725. (2010)

Ronald Breslow, Mindy Levine, and Zhen-Ling Cheng, “Imitating Prebiotic Homochirality on Earth,” Orig. Life Evol. Biosph. 40, 11-26. (2010)

T. Dadosh, J. Sperling, G. W. Bryant, R. Breslow, T. Shegai, M. Dyshel, G. Haran, I. Bar-Joseph,  “Plasmonic Control of the Shape of the Raman Spectrum of a Single Molecule in a Silver Nanoparticle Dimer.“  ACS Nano 3(7), 1988-1994. (2009)

R. Breslow, “Nature: a Model System for Chemists,” Wiley Encyclopedia of Chemical Biology 3, 277-284. (2009)

R. Breslow, “Vorinostat”, Molec. Intervent. 9, 114-115. (2009)  

Rachid Skouta, Sujun Wei, and Ronald Breslow, “High Rates and substrate selectivities in water by polyvinylimidazoles as transaminase enzyme mimics with hydrophobically bound pyridoxamine derivatives as coenzyme mimics,” J. Am. Chem. Soc. 131, 15604-15605. (2009)

Sujun Wei, Jianing Wang, Scott Venhuizen, Rachid Skouta and Ronald Breslow, “Dendrimers in solution can have their remote catalytic groups folded back into the core: Enantioselective transaminations by dendritic enzyme mimics-II,” Bioorg. Med. Chem. Lett., 19, 5543-5546. (2009)

R. Breslow, “Reply to Bada: The relevance of meteoritic alpha-methyl amino acids to prebiotic homochirality,” published Online Proc. Natl. Acad. Sci. USA 30 July 2009.

Ronald Breslow and Zhan-Ling Cheng, “On the origin of terrestrial homochirality for nucleosides and amino acids,” PNAS, 106, 9144-9146. (2009)

S. T. Schneebeli, M. L. Hall, R. Breslow, and R. Friesner, “Quantitative DFT Modeling of the Enantiomeric Excess for Dioxirane-Catalyzed Epoxidations,” J. Am. Chem. Soc. 131, 3965-3973. (2009)

“Biomimetic Chemistry: Biology as an Inspiration” Ronald Breslow, J. Biol. Chem. 284, 1337-1342 (2009)

“On the Origin of Terrestrial Homochirality for Nucleosides and Amino Acids” Ronald Breslow, Zhan-Ling Cheng, PNAS 106, 9144-9146 (2009)

“Quantitative DFT Modeling of the Enantiomeric Excess for Dioxirane-Catalyzed Epoxidations” S. T. Schneebeli, M. L. Hall, Ronald Breslow, Richard Friesner, J. Am. Chem. Soc. 131, 3965-3973 (2009)

“Artificial Enzymes with Thiazolium and Imidazolium Coenzyme Mimics” Huanyu Zhao, Frank W. Foss, Jr., Ronald Breslow, J. Am. Chem. Soc. 130, 12590-12591 (2008)

“Biomimetic Catalysis” R. Breslow, D. Austin (ed.), Chemical Biology: The role of Chemistry in our Fundamental Understanding of Biology” The Biomedical & Life Sciences Collection, Henry Stewart Talks, Ltd, London (2008)

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

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

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

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

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