Department of Chemistry Columbia University Havemeyer Hall, MC 3114 3000 Broadway New York, NY 10027 Tel: (212) 854-3934 Fax: (212) 932-8273 email: ndb1@columbia.edu Editor of Journal Chirality

Research Interests

    We are interested in the absolute configurational and conformational studies by electronic circular dichroism (ECD), in particular, by the exciton chirality, a sensitive nonempirical solution method. Based on this method extremely versatile microscale protocols for structural analysis have been developed and performed at low microgram or even at the  nanogram level.

    Recent developments include a supramolecular approach in absolute configurational assignments of secondary alcohols, primary and secondary amines, carboxylic acids and more complex natural products by using auxiliary dimeric zinc-or magnesium porphyrin tweezers as hosts.

    We are also involved in theoretical studies on the mechanism and conformational aspects of porphyrin/porphyrin interactions and development of porphyrin-based DNA probes and sensors. Other studies include development of chemical/chiroptical protocols for determination of absolute configuration of natural products by using sensitivity enhanced fluorescence detected circular dichroism (FDCD) or by theoretical simulation of ECD and ORD spectra.

Recent Representative Publications

Berova, N.; Ellestad, G. A.; Harada, N, Modern Methods in Natural Product Chemistry: Characterization by Circular Dichroism Spectroscopy, In Comprehensive Natural Products II Chemistry and Biology; Mander, L., Lui, H.-W, Eds.; Elsevier: Oxford, 2010 [Vol. 9 ] pp. 91-147.

Amplification of Chirality in Monodisperse, Enantiopure Alleno-Acetylenic Oligomers, P. Rivera-Fuentes, J.- L. Alonso-Gómez, A. G. Petrovic, F. Santoro, N. Harada, N. Berova, and F. Diederich , Angew. Chem., 2010 ,49, 2247-2250.

CD-sensitive Zn-porphyrin tweezer host-guest complexes. Part 2: cis- and trans-3-Hydroxy-4-aryl/alkyl-ß-Lactams. A case study, Chen. Y.; Petrovic, A.; Roje, M.; Pescitelli, G.; Yang, Y.; Kayser, M.; Berova , N. and Proni, G. Chirality, 2010, 22, 140-152.

CD-sensitive Zn-porphyrin tweezer host-guest complexes. Part 1: MC/OPLS-2005 computational approach for predicting preferred interporphyrin helicity, Petrovic, A.; Chen. Y.; Pescitelli, G.; Berova, N. and Proni, G. Chirality, 2010, 22, 129-139.

Role of Environmental Factors on the Structure and Spectroscopic Response of 5’- DNA-Porphyrin- Conjugates Due to Changes in Porphyrin-Porphyrin Interaction, Mammana, A.; Pescitelli, G.;  Asakawa, T; Jockusch, S Petrovic, A. G. ; Monaco, R. R.; Purrello, R.; Turro, N. J.; Nakanishi, K.; Ellestad, G.E.; Balaz, M. and Berova. N. Chemistry-Eur. J. 2009, 15,11853-11866.

Probing Molecular Chirality by CD-Sensitive Dimeric Metalloporphyrin Hosts, Berova, N.; Pescitelliu, G.; Petrovic, A.G.; Proni, G., Chem. Comm. 2009, 5958-5980.

An Enantiomerically Pure Alleno-Acetylenic Macrocycle: Synthesis and Rationalization of its Outstanding Chiroptical Response, J-Lorenzo Alonso-Gómez, P. Rivera-Fuentes, N. Harada, N. Berova, and F. Diederich, Angew. Chem., 2009, 48, 5545-5548.

Chiral Induction from Allenes Into Twisted 1,1,4,4-Tetracyanobuta-1,3-dienes (TCBDs): Conformational Assignment by Circular Dichroism (CD) Spectroscopy, J.- L. Alonso-Gómez, A. G. Petrovic, N. Harada, P. Rivera-Fuentes, N. Berova, and F.  Diederich, Chemistry-Eur. J. 2009, 15, 8396-8400.

Absolute Configuration of Actinophyllic Acid as Determined through Chiroptical Data, Taniguchi, T.; Martin, C. L.; Monde, K.; Nakanishi, K.; Berova, N. and Overman, L.E. J. Nat. Prod. 2009, 72, 430-432.

Interactions of a Tetraanionic Porphyrin with DNA: from a Z-DNA Sensor to a Versatile Supramolecular Device; D’Urso A.: Mammana, A.; Balaz, M.; Holmes, A. E; Berova, N.; Lauceri R. and Purrello. R., J. Am. Chem. Soc. 2009, 131, 2046-2047.

Chiral Sulfinates Studied by Optical Rotation, ECD and VCD: the Absolute Configuration of a Cruciferous Phytoalexin Brassicanal C, Taniguchi, T.; Monde, K.; Nakanishi, K.; Berova, N., Org. and Biomolec. Chem. 2008, 6, 4399-4405.

Synthesis and characterization of water-soluble free-base, zinc and copper porphyrin-oligonucleotide conjugates, A.Mammana, T. Asakawa, K-B.-Jensen, A. Wolfe, S. Chaturantabut, Y. Otani, X. Li, Z. Li, K. Nakanishi, M. Balaz, G. A. Ellestad, and N.Berova, Bioorg. & Medicinal Chem. 2008, 16, 6544-6551.

Inherent Chirality Dominates the Visible/Near–Ultraviolet CD Spectrum of Rhodopsin, G. Pescitelli, S. Narasimha, P. Salvadori, K. Nakanishi, N. Berova, and R, Woody, J. Am. Chem. Soc. 2008, 130, 6170-6181.

Reassessing the Structure of Pyranonigrin,  Schlingmann, G. ; Bigelis, R.; Yang, H.Y.; Koehn, K.E.; Carter, G.T.; He, H.; Taniguchi, T. and Berova. N. J. Nat. Prod. 2007, 70, 1180-1187.

Porphyrins as Spectroscopic Sensors for Conformational Studies of DNA, Balaz, M; Bitsch-Jensen, K; Mammana, A; Ellestad, GA; Nakanishi, K and Berova, N.  Pure & Appl. Chem. 2007, 79, 801-809

Synthesis and Energy Transfer in Multiporphyrin Arrays Self-Assembled with Hydrogen Bonding Recognition Groups and Comparison with Covalent Steroidal Models” Balaban, TS; Berova, N; Drain, C-M; Hauschild, R; Huang, X; Kalt, H; Lebedkin, S; Lehn, J-M; Nifaitis, F; Pescitelli, G.; Prokhorenko, VI; Riedel, G; Smeureanu, G and Zeller, J., ChemIstry: A Eur. J.  2007, 13, 8411-8427.

Application of Electronic Circular Dichroism in Configurational and Conformational Analysis of Organic Compounds, Berova, N.; Di Bari, L. and Pescitelli, G., Chemical Society Reviews, 2007,36, 914-931.

Enantioselective Synthesis of 3-Methylisochromans and Determination of Their Absolute Configurations by Circular Dichroism, Kerti, G.; Kurtan, T.; Illyes, T-Z; Köver, K.E.; Solyom, S.; Pescitelli, G.; Fujioka, N.; Berova, N. and Antus. S. Eur J. Org. Chem. 2007, 296-305.

Single-Walled Carbon Nanotubes Exhibit Circular Dichroism when Wrapped with DNA, Dukovic, G.; Doak, P.; Balaz, M.; Berova, N.; Zheng, M.; Semke, E. and Brus, L. E. J. Am. Chem. Soc. 2006 128, 9004-9005.

Determination of Absollute configurations of Flexible Molecules: Synthesis and Theoretical Simulation of Electronic Circular Dichroism /Optical Rotation of Some Pyrrolo[2,3-b]Indoline Alkaloids – A Case Study , Giorgio, E.; Tanaka, K.; Verotta, L.; Nakanishi, K.; Berova, N. and  Rosini, C., Chirality, 2007, 19, 434-445

Conjugated Porphyrins as CD Reporter of the Salt-Induced B to Z- DNA Transition,
Balaz, M.; Li, B. C.; Steinkruger, J.; Ellestad, G.A.; Nakanishi, K. and Berova, N. Org. Biomol. Chem .2006, 4, 1865-1867.

Tetraarylporphyrin as a Selective Molecular Cap for the Non Watson-Crick G: A Base Pair Sequences, Balaz, M.; Li, B.C.; Jockush, S.; J.; Ellestad, G. E.; Berova, N., Angew. Chem. 2006, 45, 3530-3533.

Circular Dichroism of Heterochromophoric and Partially Regenerated Purple Membrane: Search for Exciton Coupling, Karnaukhova, E.; Vasileiou, C.; Wang, A.; Berova, N.; Nakanishi, K.; Bohran, B. Chirality, 2006, 18, 72- 83.

5’-Porphyrin-Oligonucleotide Conjugates: Neutral Porphyrin-DNA Interactions, Balaz, M.; Steinkruger, J.; Ellestad, G. E.; Berova, N. Org. Letters, 2005, 7, 5613-5616.

Comparative Study of Energy-Transfer Processes in Several Porphyrin-Based Artificial Molecules, Hauschild, R.; Riedel, G.; Zeller, J.; Balaban, T. S.; Prokhorenko, V. I.; Kalt, H.; Berova, N.; Huang, X.; Pescitelli, R.; Nakanishi, K.  J. Luminescence, 2005, 112, 454-457.

A Cationic Zinc Porphyrin as a Chiroptical Sensor for Z-DNA, Balaz, M.; De Napoli, M.; Holmes, A.; Mammana, A.; Nakanishi, K.; Berova, N.  and Purrello, R. Angew. Chem. 2005, 44, 4006-4009.

Theoretical Simulation of the Electronic Circular Dichroism Spectrum of Calicheamicin, Giorgio, E.; Tanaka, K.; Ding, W-D.; Krishnamurthy, G.; Pitts, K.; Ellestad, G. A.; Rosini, C., and Berova, N.  Biorg. and Medicinal Chemistry, 2005, 13, 5072-5079.

Three Challenges towards the Assignment of Absolute Configuration of Gymnocin-B, Tanaka, K.; Itagaki, Y.; Satake, M.; Naoki, H.; Yasumoto, T.; Nakanishi, K.; Berova, N. J. Am. Chem. Soc., 2005, 127, 9561-9570.

Chiral Recognition of Cyclic a-Hydroxyketones by CD-Sensitive Zinc Tetraphenylporphyrin Tweezer, Ishii, H.; Chen, Y.; Miller A. R.; Karady, S.; Nakanishi, K.; Berova, N. Chirality, 2005, 17, 305-315.

Porphyrin Substituted Phosphoramidites: New Building Blocks for Porphyrin-Oligonucleotide Syntehses, Balaz, M.; Holmes, A. E.; Benedetti, M.; Proni, G.; Berova, N. Bioorg.& Med. Chem.,2005,13, 2413-2421.

Determination of the Absolute Configuration of Flexible Molecules by ab initio ORD Calculations: A Case Study with Cytoxazones and Isocytoxazones, Giorgio, E.; Roje, M.; Tanaka, K.; Hamersak, Z.; Sunic, V.; Nakanishi, K.; Rosini, C.; Berova, N. J. Org.Chem. 2005, 70, 6557- 6563.

Synthesis and Circualr Dichroism of Tetraarylporphyrin-Oligonucleotide Conjugates, Balaz, M.; Holmes, A. E.; Benedetti, M.; Rodriguez, P. C.; Berova, N.; Nakanishi, K.; Proni, G. J. Am. Chem. Soc. 2005, 127, 2472-2473.

Fluorescence Detected Exciton Coupled Circular Dichroism: Development of New Fluorescent Reporter Groups for Structural Studies, Tanaka, K.; Pescitelli, G.; Nakanishi, K.; Berova, N. Monatshefte für Chemie, Chemistry Monthly, 2005, 136, 367-395.

Development of a Universal Ellipsoidal Mirror Device for Fluorescence Detected Circular Dichroism (FDCD) –Elimination of Polarization Artifacts, Nehira, T.; Tanaka, K.; Takakuwa, T.; Ohshima, C.; Masago, H.; Pescitelli, G.; Wada, A.; Berova, N. Applied Spectroscopy, 2005, 59, 121-125.

Absolute Configurational Determination of an All-trans-retinal Dimer Isolated from Photoreceptor Outer Segments, Fishikin, N.; Pescitelli, G.; Sparrow, J.; Nakanishi, K.; Berova, N. Chirality, 2004, 16, 637-641.

Detection of Zinc Ions by Differential Circularly Polarized Fluorescence Excitation, Dai, Z.; Proni, G.; Mancheno, D.; Karimi, S.; Berova, N.; Canary, J. W. J. Am. Chem. Soc., 2004, 126, 11760-11761

Absolute Configuration of a Hydroxyfuranoid Acid from the Pelage of Genus of Bos (Bovidae: Mammalia), 18-(6S,9R,10R)-Bovidic Acid, Ishii, H.; Krane, S.; Itagaki, Y.; Berova, N.; Nakanishi, K.; Weldon, P. J. J. Natural Products, 2004, 67, 1426-1430.

Determination of the Absolute Configuration of Anisotome Irregular Diterpenes: Applicationof CD and NMR Methods, Van Klink, J. W.; Baek, S.-H.; Barlow, A. J.; Ishii, H.; Nakanishi, K.; Berova, N.; Perry, N. B.; Weavers, R. T. Chirality, 2004, 16, 549-558.

Primary Events in Dim Light Vision: A Chemical and Spectroscopic Approach Toward Understanding Protein/Chromophore Interactions in Rhodopsin, Fishkin, N.; Berova, N.; Nakanishi, K. The Chemical Records, 2004, 4, 120-135.

Trans-Diaryl Epoxides: Asymmetric Synthesis, Ring-Opening and Absolute Configurations, Solladie-Cavallo, A.; Roje, M.; Giraud-Roux, M.; Chen, Y.; Berova, N.; Sunjic, V. Chirality, 2004, 16, 196-203.

Absolute Stereochemistry of Dihydrofuroamgelicins Bearing C-8 Substituted Double Bonds: A Combined Chemical/Exciton Chiraity Protocol, Tanaka, K.; Pescitelli, G.; DiBari, L.; Xiao, T. L.; Nakanishi, K.; Armstrong, D. W.; Berova, N. Organic & Biomolecular Chemistry, 2004, 2, 48-58.

Synthesis and Spectroscopic Properties of Methylbenzoate Derivative of Tetrabenzoporphyrin. Application to Circular Dichroism Studies, Giraud-Roux, M.; Proni, G.; Nakanishi, K.; Berova, N.  Heterocycles, 2003, 61, 417-432.

Absolute Stereochemistry of Allylic Alcohols, Amines and Other Ene Moieties: A Microscale Cross Metathesis/ Exciton Chirality Protocol, Tanaka, K.; Nakanishi, K.; Berova, N. J. Am. Chem. Soc. 2003, 125, 10802-10803.

Magnesium Tetraarylporphyrin Tweezer: a Sensitive Host for Recognition of a-Chiral Carboxylic Acids, Proni, G.; Pescitelli, G.; Huang, X.; Nakanishi, K.; Berova, N.  J. Am. Chem. Soc. 2003, 125, 12914-12927.

Theoretical Analysis of the Porphyrin – Porphyrin Exciton Interaction in Circular Dichroism Spectra of Dimeric Tetraarylporphyrins, Pescitelli, G.; Gabriel, S.; Wang, Y.; Fleischhauer, J.; Woody, R. W.; Berova, N. J. Am. Chem. Soc. 2003, 125, 7613-7628.

Assignment of Absolute Configurations of a Chiral Phenyl-Substituted Dihydrofuroangelicin, Pascitelli, G.; Berova, N.; Xiao, T. L.; Rozhkov, R. V.; Larock, R. C.; D. W. Armstrong. Organic & Biomolecular Chemistry, 2003, 1, 186-190.

Configurational Assignment of a-Chiral Carboxylic Acids by Complexation to dimeric Zn-porphyrin: Host/Guest Structure, Chiral Recognition and Circular Dichroism, Proni, G.; Pescitelli, G.; Huang, X.; Quraishi, N. Q.; Nakanishi, K.; Berova, N. Chem. Comm. 2002, 1590-1591.

Absolute Configurational Assignments of Secondary Amines by CD-Sensitive Dimeric Zinc Porphyrin Host, Huang, X.; Fujioka, N.; Pescitelli, G.; Koehn, F. E.; Williamson, Thomas R.; Nakanishi, K.; Berova, N.  J. Am. Chem. Soc.  2002, 124, 10320-10335.
Solution and Biologically Relevant Conformations of Enantiomeric 11-cis-Locked Cyclopropyl Retinal, Fujimoto, Y.; Fishkin, N.; Pescitelli, G.; Decateure, J.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 2002, 124, 7294-7302

 (R)-(+) and (S)-(-)-1-(9-Phenanthryl)-ethylamine: Assignment of Absolute Configuration by CD-Twezeer and VCD Methods, and Difficulties Encountered with the CD-Exciton Chirality Method, Solladié-Cavallo, A.; Marsol, C.; Pescitelli, G.; Di Bari, L.; Salvadori, P.; Huang, X.; Fujioka, N.; Berova, N.; Cao, X.; Freedman, T. B.; L. A. Nafie. Eur. J.Org. Chem, 2002, 1788-1796.

Synthesis of 11-cis –locked Bicyclo[5.1.0] octanyl Retinal and an Enantioselective Binding to Bovine Opsin, Fujimoto, Y.; Xie, R.; Tully, S. E.; Berova, N.; Nakanishi, K. Chirality, 2002,14, 340-346.

On the Bioactive Conformation of the Rhodopsin Chromophore. Absolute Sense of Twist Around the 6-s cis bond, Fujimoto, Y.; Ishihara, J.; Maki, S.; Fujioka, N.; Wang, T.; Furuta, T.; Fishkin, N.; Borhan, B.; Berova, N.; Nakanishi, K. Chem.-Eur. J, 2001, 7, 4198-4204.

Absolute Stereochemistry of the Spiroxins, Wang, T.; Shirota, O.; Berova, N.; Nakanishi, K.; McDonald, L. A.; Barbieri, L. R.; Carter, G. T.  Can. J. Chem., 2002, 79, 1786-1791.

Determining Absolute Configuration in Flexible Molecules: A Case Study. Specht, K.M.; Nam, J.; Ho D. M.; Berova, N.; Kondru, R. K.; Beratan, D. N.; Wipf, P.; Pascal, Jr., R. A.; Kahne, D.  J. Am. Chem. Soc. 2001, 123, 8961-8966.

Chiral Recognition by CD-Sensitive Dimeric Zinc Porphyrin Host. Part 2. Structural Studies of Host-Guest Complexes with Chiral Alcohol and Monoamine Conjugates, Kurtán, T.; Nesnas, N.; Koehn, F.E.; Li, Y.-Q.; Nakanishi, K.; Berova, N.  J. Am. Chem. 2001, 123, 5974-5982.

Chiral Recognition by CD-Sensitive Dimeric Zinc Porphyrin Host. Part 1. Chiroptical Protocol for Absolute Configurational Assignments of Monoalcohols and Primary Monoamines, Kurtán, T.; Nesnas, N.; Li, Y.-Q.; Huang, X.; Nakanishi, K.; N. Berova. J. Am. Chem. Soc. 2001, 123, 5962-5973.

Biological Implications of Conformational Flexibility in Ouabain: Observations with Ouabain Two Phosphate Isomers, Kawamura, A.; Abrell, L. M.; Maggiali, F.; Berova, N.; Nakanishi, K.; Labutti, J.; Magil, S.; Haupert, Jr., G. T.; Hamlyn, J. M. Biochemistry, 2001, 40, 5835-5844.

Broad Spectrum Antimicrobial Activity of Hemoglobin. Parish, C.A.; Jiang, H.; Tokiwa, Y.; Berova, N.; Nakanishi, K.; McGabe, D.; Zuckerman, W.; Xia, M.M.; Gabey, J.E. Bioorganic and Medicinal Chemistry, 2001, 9, 377-382.

Absolute Configurational Assignment of 3-Hydroxy Carotenoids. Anderson, T.; Borhan, B.; Berova, N.; Nakanishi, K.; Haugan, J.A.; Liaaen-Jensen, S. J. Chem. Soc. Perkin Trans. 2000,1,2409-2414.

The Relative and Absolute Configurations of Ganefromycin. Anderson, T.; Berova, N.; Nakanishi, K. ; Carter, G.T. Organic Letters. 2000,2, 919-922.

Dong, J-G.; Kawamura, A.; Guo, J.; Nakanishi, K.; Berova, N. In Structure Determination of Saponins with Cardiotonic Activity by Circualar Dichroism; Oleszek W; Marston, A., Eds.; Saponins in Food, Feedstuff and Medicinal Plants; Kluwer Academic: Dordrecht, 2000; pp 79-94.

Porphyrins and Metalloporhyrins: Versatile Circular Dichroic Reporter Groups for Structural Studies. Huang, X.; Nakanishi, K.; Berova, N. Chirality. 2000,12,237-255.

Absolute Stereochemistry of Strevertenes. Guo, J.; Nakanishi, K.; Berova, N.; Schlingmann, G.; Carter, G. Chirality. 2000,12,43-51.

Zinc Porphyrin Tweezer in Host-Guest Complexation: Determination of Absolute Configuration of Primary Monoamines by Circular Dichroism. Huang, X.; Borhan, B.; Rickmann, B.; Berova, N.; Nakanishi, K. Chem.-Eur. J. 2000,6,216-224.

N. Berova and K. Nakanishi In Principles and Applications of Exciton Chirality Method; Berova, N.; Nakanishi, K.; Woody, R., Eds.; Circular Dichroism - Principles and Applications;Wiley-VCH: New York, 2000; pp 337-382.

Kawamura, A.; Nakanishi, K.; Berova, N. Use of Circular Dichroism for Assigning Stereochemistry of Sphingosines and Long Chain Bases, in Methods in Enzymology , Vol. 312, Sphingolipid Metabolism and Cell Signaling, Merrill, A.H., Jr. and Hannun Y.A.; Eds.; Academic Press, San Diego, Vol. 312. Part B, 2000, pp. 217-227. 

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Last updated: March 20, 2007