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

• 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. in press.

• The Absolute Configuration of 1-(3’,4’-Dihydroxycinnamoyl)cyclopentane-2,3-diol from the Amazonian Tree Chimarrhis turbinate, Cardoso, C. L.; Bolzani, V. D. S.; Siqueira, D.H., Ishii, H.; Berova, N.; Nakanishi, K. J. Nat. Prod., 2006, 69, 1046-1050.

• 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.  in press

• 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, DOI:10.1039/B515476F

• 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.

• Theoretical Simulation of Electronic Circular Dichroism and Optical Rotation of Some Pyrrolo[2,3-b]Indoline Alkaloids, Giorgio, E.; Tanaka, K.; Verotta, L.; Nakanishi, K.; Berova, N. and  Rosini, C. Chirality, 2007 (in press)

• 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.

• 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, 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.

• Unique Reactivity of ?-Alkoxy Ginkgolide Lactones to Nucleophilic Reagents: Preparation of New Lactol Derivatives, Tanaka, K.; Pimentel, M.; Berova, N.; and Nakanishi, K. Bull. Chem. Soc. Jap. 2005, 78, 1843-1850.

• 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 ?-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.

• Preparation of Ginkgolide and F-seco – Ginkgolide Lactols: The Unique Reactivity of ?-Hydroxy Lactones towards NaBH4, Tanaka, K.; Kester, K. D.; Berova, N.; Nakanishi, K. Tet. Letters, 2005, 46,531-534.

• 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 ? 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.

• Circular Dichroism and Visual Science, Nakanishi, K.; Berova, N. in “Progress in Biological Chirality” Palyi, G.; Zucci, C.; Caglioti, L. Eds. Elsevier, Oxford, GB), 2004, Ch. 19, 237-251.

• 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.

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

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

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

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

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

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

• Assignment of Absolute Configurations of a Chiral Phenyl-Substituted Dihydrofuroangelecin, G. Pescitelli, N. Berova, T. Xiao, R. V. Rozhkov, R. C. Larock ,D. Armstrong, Org. Biom. Chem. 2003, 1, 186.

• Absolute Configurational Assignments of Secondary Amines by CD-Sensitive Dimeric Zinc Porphyrin Host, J. Am. Chem. Soc. 2002, 124, 10320.

• Solution and Biologically Relevant Conformations of Enantiomeric 11-cis-Locked Cyclopropyl Retinal, Y. Fujimoto, N. Fishkin, G. Pescitelli, J. Decateure, N. Berova, K. Nakanishi, 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, A. Solladié-Cavallo, C. Marsol, G. Pescitelli, L. Di Bari, P. Salvadori, X. Huang, N. Fujioka, N. Berova, X. Cao, T. B. Freedman, and  L. A. Nafie, Eur. J. Org. Chem. 2002, 1788.

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

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

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

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

• Porphyrins and Metalloporhyrins: Versatile Circular Dichroic Reporter Groups for Structural Studies (review), by X. Huang, K. Nakanishi and N. Berova, Chirality, 2000, 12, 237. 

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

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

• Fluorescence-detected Exciton-coupled Circular Dichroism: Scope and Limitation in Structural Studies of Organic Molecules, T. Nehira, C. A. Parish, S. Jockusch, N. J. Turro, K. Nakanishi, and N.Berova, J. Am. Chem. Soc. 1999, 121, 8681-8691
  

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Last updated: March 20, 2007