个人简介

B.S., 1988, Univ. of California, Davis Ph.D., 1995, Univ. of California, Davis Postdoctoral Fellow, 1995-1998, Columbia Univ. Award Organization Division Level Code Type Code Start Date End Date Teacher-Scholar Award Michigan State University College of Natural Science Professional Honors 2004 University Teacher-Scholar Award Michigan State University Professional Honors 2002 Ph.D. University of California, Davis Graduate Degree 1995 Postdoctoral Fellow Columbia University Postdoctoral Fellowship 1995 1998 Outstanding Teaching Assistantship Award University of California, Davis Professional Honors 1994 Full foreign tuition fellowship University of California, Davis Professional Fellowship 1990 1993 Bradford Borges Graduate Scholarship Graduate Scholarship 1989 Bachelor of Science University of California, Davis Undergraduate Degree 1988 University of California Regents Scholarship University of California, Davis Undergraduate Scholarship 1987 1988 University of California Undergraduate Scholarship University of California, Davis Undergraduate Scholarship 1985 1986 Member Sigma Xi Honor Society Michigan State University Professional Honors

研究领域

Biological Organic

(Research Description PDF - 1027 kb) The research interests of our lab can be subdivided into the three main areas of Bioorganic Chemistry, Synthetic Chemistry, and Organic Spectroscopy. Our Bioorganic Chemistry efforts are geared towards elucidation of the interaction of bioactive compounds with receptors and proteins. We rely heavily on de novo protein design and mimicry of natural systems to better understand how certain biological processes occur. As an example, we have initiated research into designing protein mimics of rhodopsin, the protein responsible for vision, which can bind retinal as a protonated Schiff base [PSB] (same binding mode as in rhodopsin). These protein mimics are used to investigate the wavelength regulation mechanism that enables color vision. Currently we are exploring the potential to use our engineered proteins as colorimetric and fluorescent proteins for cellular tagging and intracellular pH sensors. Our Synthetic Chemistry program is generally focused on the development of new reactions that utilize simple organic molecules and through designed manipulations lead to more complex systems. In most cases, our methodologies lead to the production of heterocycles with regio- and stereocontrol. These transformations are then highlighted in total syntheses of natural products that exhibit interesting biological activities. Recently we have reported the catalytic asymmetric chlorolactonization of alkenoic acids and unsaturated amides to furnish chiral heterocycles. These reactions are catalyzed by (DHQD)2PHAL in combination with various N-chlorinated hydantoins as the terminal chlorenium sources. Halofunctionalization of different compounds, understanding the mechanism of these transformations and the details of enantioselections are currently under investigation. In the area of Organic Spectroscopy, we are interested in developing host/guest systems that can be used in the absolute stereochemical determination of chiral compounds. We accomplish this through the design and synthesis of chromophoric receptors, which upon binding with the chiral compound function as reporters of chirality. We rely heavily on Circular Dichroism (CD) as the tool for observing the host/guest interactions between the chiral compounds and the receptors. In particular, we will take advantage of the excitonic coupling between independently conjugated chromo--phores that make up the receptors to establish non-empirical guidelines for the absolute stereochemical determination of asymmetric centers.

近期论文

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"Turn-On" Protein Fluorescence: In Situ Formation of Cyanine Dyes Yapici, I.; Lee, K. S. S.; Berbasova, T.; Nosrati. M.; Jia, X.; Vasileiou, C.; Santos, E. M.; Geiger, J. H.; Borhan, B. Science, 2 Science 2012 Act. Cryst. Sec. D-Biol. Cryst. 2014, 70, 3226-3232 Structures of Holo Wild-Type human Cellular Retinol Binding Protein II (hCRBPII) Bound to Retinol and Retinal Nossoni, Z.; Assar, Z.; Yapici, I.; Nosrati, M.; Wang, W.; Berbasova, T.; Vasileiou, C.; Borhan, B.; Geiger, J. H. Science, 2 Science 2012 J. Am. Chem. Soc. 2014, 136, 13355-13362. A New Tool to Guide Halofunctionalization reactions: The Halenium Affinityu (HalA) Scale Ashtekar, K. D.; Marzijarani Salehi, N.; Jaganathan, A.; Holmes, D.; Jackson, J. E.; Borhan, B. Science, 2 Science 2012 Org. Lett. 2014, 16, 3616-3619. Chlorosulfonamide Salts are Superior Electrophilic Chlorine Precursors for the Organocatalytic Asymmetric Chlorocyclization of Unsaturated Amides Jaganathan, A.; Borhan, B. Science, 2 Science 2012 J. Am. Chem. Soc. 2014, 136, 550-553. Point-to-Axial Chirality Transfer—A New Probe for "Sensing" the Absolute Configurations of Monoamines Anyika, M.; Gholami, H.; Ashtekar, K. D.; Acho, R.; Borhan, B. Science, 2 Science 2012 J. Am. Chem. Soc. Mass Spec. 2014, 25, 141-148 Quantification of Competing H3PO4 vs HPO3 + H2O Neutral Losses from Regioselective 18O-Labeled Phosphopeptides Cui, L.; Yapici, I.; Borhan, B.; Reid, G. E. Science, 2 Science 2012 BioEssays. 2014, 36, 65-74 The Photochemical Determinants of Color Vision Wang, W.; Geiger, J. H.; Borhan, B. Science, 2 Science 2012 Tetrahedron. 2013, 69, 9469-9474 7-beta- and 10-beta-Hydroxylated congeners of CAF-603; elucidation of absolute configuration of CAF-603 family, and their SAR studies in the anti-fungal activity Yasamura, R.; Ashtekar, K. D.; Tonouchi, A.; Nehira, T.; Borhan, B.; Hashimoto, M. Science, 2 Science 2012 J. Am. Chem. Soc. 2013, 135, 16111-16119 Rational Design of a Colorimetric pH Sensor from a Soluble Retinoic Acid Chaperone Berbasova, T.; Nosrati, M.; Vasileiou, C.; Wang, W.; Lee, K. S. S.; Yapici, I.; Geiger, J. H.; Borhan, B. Science, 2 Science 2012 J. Am. Chem. Soc. 2013, 135, 14524-14527 Dissecting the Stereocontrol Elements of a Catalytic Asummetric Chlorolactonization: Syn Addition Obviates Bridging Chloronium Yousefi, R.; Ashtekar, K. D.; Whitehead, D. C.; Jackson, J. E.; Borhan, B. Science, 2 Science 2012 J. Am. Chem. Soc. 2013, 135, 14806-14813 Kinetic Resolution of Unsaturated Amides in a Chlorocyclization Reaction: Concomitant Enantiomer Differentiation and Face Selective Alkene Chlorination by a Single Catalyst Jaganathan, A.; Staples, R. J.; Borhan, B. Science, 2 Science 2012 J. Phys. Chem. B 2013, 117, 10053-10070 Toward an Understanding of the Retinal Chromophore in Rhodopsin Mimics Huntress, M. M.; Gozem, S.; Malley, K. R.; Jailaubekov, A. E.; Vasileiou, C.; Vengris, M.; Geiger, J. H.; Borhan, B.; Shapiro, I.; Larsen, D. S.; Olivucci, M. Science, 2 Science 2012 Chem. Europ. J. 2013, 19, 9015-9021 Solvent-Dependent Enantiodivergence in the Chlorocyclization of Unsaturated Carbamates Garzan, A.; Jaganathan, A.; Salehi-Marzijarani, N.; Yousefi, R.; Whitehead, D. C.; Jackson, J. E.; Borhan, B. Science, 2 Science 2012 Science 2012, 338, 1340-1343 Tuning the Electronic Absorption of Protein-Embedded All-trans-Retinal Wang, W.; Nossoni, Z.; Berbasova, T.; Watson, C.; Yapici, I.; Lee, K. S. S.; Vasileiou, C.; Geiger, J. H.; Borhan, B. Science, 2 JMolMod J. Mol. Mod.2012, 18, 4547-4556 Selectivity of Labeled Bromoethylamine for Protein Alkylation Marincean, S.; Rabago-Smith, M.; Beltz, L.; Borhan, B. JMolMod OrgLett.jpg Org. Lett. 2012, 14, 3592-3595 3,4-Dihydroxypyrrolidines via Modified Tandem Aza-Payne/Hydroamination Pathway Kulshrestha, A.; Salehi-Marzijarani, N.; Ashtekar, K. D.; Staples, R.; Borhan, B. OrgLett JACS.jpg JACS 2012, 134, 9026-9029 Absolute Configuration of 1,n-Glycols: A Nonempirical Approach to Long-Range Stereochemical Determination Li, X.; Burrell, C.; Staples, R.; Borhan, B. OrgLett EJOC.gif Eur. J. Org. Chem. 2012, 12, 3261-9029 Conformational Preference in Bis(porphyrin) Tweezer Complexes: A Versatile Chirality Sensor for Chiral Carboxylic Acids Tanasova, M.; Borhan, B. EJOC ChemPlusChem. 2012, 77, 273-276 Probing Wavelength Regulation with an Engineered Rhodopsin Mimic and a C-15-Retinal Analogue Lee, K. S. S; Berbasova, T.; Vasileiou, C.; Jia, X.; Wang, W.; Choi, Y.; Nossoni, F.; Geiger, J. H.; Borhan, B. EJOC OrgLett.jpg OrgLett 2011, 13, 5732-5735 Development of a Formal Catalytic Asymmetric [4+2] Addition of Ethyl-2,3-butadienoate with Acyclic Enones Ashtekar, K. D.; Staples, R. J.; Borhan, B. EJOC ChemEurJ.gif Chem. Europ. J. 2011, 17, 12326-12339 Selectivity in the Addition Reactions of Organometallic Reagents to Aziridine-2-carboxaldehydes: The Effects of Protecting Groups and Substitution Patterns Kulshrestha, A.; Schomaker, J. M.; Holmes, D.; Staples, R. J.; Jackson, J. E.; Borhan, B. EJOC OrgBiomolChem.jpeg Org. Biomol. Chem. 2011, 9, 4741-4744 Catalytic Oxidative Cleavage of Olefins Promoted by Osmium Tetroxide and Hydrogen Peroxide Hart, S. R.; Whitehead, D. C.; Travis, B.; Borhan, B.