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Borhan Group Publications

(Publication List With Graphics and Links)

 

  1. Gholami, H.; Zhang, J.; Anyika, M.; Borhan, B. "Absolute Stereochemical Determination of Asymmetric Sulfoxides via Central to Axial Induction of Chirality",Org. Let. 2017, 19, 1722-1725.
  2. Zhang, J.; Gholami, H.; Ding, X.; Chun, M.; Vasileiou, C.; Nehira, T.; Borhan, B. “Computationally Aided Absolute Stereochemical Determination of Enantioenriched Amines”, Org. Let. 2017, 19, 1362-1365.
  3. Soltanzadeh, B.; Jaganathan, A.; Yi, Y.; Yi, H.; Staples, R. J.; Borhan, B. "Highly Regio- and Enantioselective Vicinal Dihalogenation of Allyl Amides", J. Am. Chem. Soc. 2017, 139(6), 2132-2135.
  4. Assar, Z.; Nossoni, Z.; Wang, W.; Santos, E. M.; Kramer, K.; McCormack, C.; Vasileiou, C.; Borhan, B.; Geiger, J. H. "Domain-Swapped Dimers of Intracellular Lipid-Binding Proteins: Evidence for Ordered Folding Intermediates", Structure 2016, 24(9), 1590-1598.
  5. Ashtekar, K. D.; Ding, X.; Toma, E.; Sheng, W.; Gholami, H.; Rahn, C.; Reed, P.; Borhan, B. "Mechanistically Inspired Route toward Hexahydro-2H-chromenes via Consecutive [4+2] Cycloadditions", Org. Lett. 2016, 18(16), 3976-3979.
  6. Nosrati, M.; Berbasova, T.; Vasileiou, C.; Borhan, B.; Geiger, J. H. "A Photoisomerizing Rhodopsin Mimic Observed at Atomic Resolution", J. Am. Chem. Soc. 2016, 138(28), 81802-8808.
  7. Ashtekar, K.D.; Vetticatt, M.; Yousefi, R.; Jackson, J. E.; Borhan, B. "Nucleophile-Assisted Alkene Activation: Olefins Alone are Often Incompetent, J. Am. Chem. Soc. 2016, 138(26), 8114-8119.
  8. Gholami, H.; Anyika, M.; Zhang, J.; Vasileiou, C.; Borhan, B. "Host-Guest Assembly of a Molecular Reporter with Chiral Cyanohydrins for Assignment of Absolute Stereochemistry", Chem.Eur.J. 2016, 22(27), 9235-9239.
  9. Berbasova, T.; Santos, E. M.; Nosrati, M.; Vasileiou, C.; Geiger, J. H.; Borhan, B. "Light-Activated Reversible Imine Isomerization: Towards a Photochromic Protein Switch", ChemBioChem 2016, 17, 407-414.
  10. Soltanzadeh, B.; Jaganathan, A.; Staples, R. J; Borhan, B. "Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amide", Angew. Chem. Int. Ed. Engl. 2015, 54, 9517-9522.
  11. Tanasova, M.; Anyika, M.; Borhan, B. "Sensing Remote Chirality: Stereochemical Determination of beta-, gamma-, and delta-Chiral Carboxylic Acids", Angew. Chem. Int. Ed. Engl. 2015, 54, 4274-4278.
  12. Yapici, I.; Lee, K. S. S.; Berbasova, T.; Nosrati. M.; Jia, X.; Vasileiou, C.; Santos, E. M.; Geiger, J. H.; Borhan, B. ""Turn-On" Protein Fluorescence: In Situ Formation of Cyanine Dyes", J. Am. Chem. Soc. 2015, 137, 1073-1080.
  13. Nossoni, Z.; Assar, Z; Yapici, I.; Nosrati, M.; Wang, W.; Berbasova, T.; Vasileiou, C.; Borhan, B.; Geiger, J. H. "Structures of Holo Wild-Type human Cellular Retinol Binding Protein II (hCRBPII) Bound to Retinol and Retinal", Act. Cryst. Sec. D - Biol. Cryst. 2014, 70, 3226-3232.
  14. Ashtekar, K. D.; Marzijarani Salehi, N.; Jaganathan, A.; Holmes, D.; Jackson, J. E.; Borhan, B. "A New Tool to Guide Halofunctionalization reactions: The Halenium Affinityu (HalA) Scale", J. Am. Chem. Soc. 2014, 136, 13355-13362.
  15. Jaganathan, A.; Borhan, B. "Chlorosulfonamide Salts are Superior Electrophilic Chlorine Precursors for the Organocatalytic Asymmetric Chlorocyclization of Unsaturated Amides", Org. Lett 2014, 16(14), 3616-3619.
  16. Anyika, M.; Gholami, H.; Ashtekar, K. D.; Acho, R.; Borhan, B. "Point-to-Axial Chirality Transfer—A New Probe for "Sensing" the Absolute Configurations of Monoamines", J. Am. Chem. Soc. 2014, 136, 550-553.
  17. Cui, L.; Yapici, I.; Borhan, B.; Reid, G. E. "Quantification of Competing H3PO4 vs HPO3 + H2O Neutral Losses from Regioselective 18O-Labeled Phosphopeptides", J. Am. Soc. Mass Spec. 2014, 25(1), 141-148.
  18. Wang, W.; Geiger, J. H.; Borhan, B. "The photochemical determinants of color vision", BioEssays 2014, 36(1), 65-74.
  19. Yasamura, R.; Ashtekar, K. D.; Tonouchi, A.; Nehira, T.; Borhan, B.; Hashimoto, M. "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", Tetrahedron 2013, 69(45), 9469-9474.
  20. Berbasova, T.; Nosrati, M.; Vasileiou, C.; Wang, W.; Lee, K. S. S.; Yapici, I.; Borhan, B. "Rational Design of a Colorimetric pH Sensor from a Soluble Retinoic Acid Chaperone", J. Am. Chem. Soc. 2013, 135, 16111-16119.
  21. Yousefi, R.; Ashtekar, K. D.; Whitehead, D. C.; Jackson, J. E.; Borhan, B."Dissecting the Stereocontrol Elements of a Catalytic Asummetric Chlorolactonization: Syn Addition Obviates Bridging Chloronium", J. Am. Chem. Soc. 2013, 135, 14524-14527.
  22. Jaganathan, A.; Staples, R. J.; Borhan, B. "Kinetic Resolution of Unsaturated Amides in a Chlorocyclization Reaction: Concomitant Enantiomer Differentiation and Face Selective Alkene Chlorination by a Single Catalyst", J. Am. Chem. Soc. 2013, 135, 14806-14813.
  23. Huntress, M. M.; Gozem, S.; Malley, K. R.; Jaiaubekov, A. e.; Vasileiou, C.; Vengris, M.; Geiger, J. H.; Borhan, B.; Shapiro, I.; Larsen,, ,D. S.; Olivucci, M. "Toward an Understanding of the Retinal Chromophore in Rhodopsin Mimics", J. Phys. Chem. B 2013, 117, 10053-10070.
  24. Garzan, A.; Jaganathan, A.; Salehi-Marzijarani, N.; Yousefi, R.; Whitehead, D. C.; Jackson, J. E.; Borhan, B. "Solvent-Dependent Enantiodivergence in the Chlorocyclization of Unsaturated Carbamates", Chem. Eur. J. 2013,19, 9015-9021.
  25. Wang, W.; Nossoni, Z.; Berbasova, T.; Watson, C. T.; Yapici, I.; Lee, K. S. S.; Vasileiou, C.; Geiger, J. H.; Borhan, B. "Tuning the Electronic Absorption of Protein-Embedded All-trans-Retinal", Science, 2012, 338, 1340-1343.
  26. Marincean, S.; Rabago-Smith, M.; Beltz, L.; Borhan, B. " Selectivity of Labeled Bromoethylamine for Protein Alkylation", J. Mol. Mod. 2012, 18, 4547-4556.
  27. Kulshrestha, A.; Salehi-Marzijarani, N,; Ashtekar, K. D.; Staples, R.; Borhan,B. " 3,4-Dihydroxypyrrolidines via Modified Tandem Aza-Payne/Hydroamination Pathway", Org. Lett. 2012, 14, 3592-3595.
  28. Li, X.; Burrell, C.; Staples, R. J.; Borhan, B. "Absolute Configuration of 1,n-Glycols: A Nonempirical Approach to Long-Range Stereochemical Determination", J. Am. Chem. Soc. 2012, 134, 9026-9029.
  29. Tanasova, M.; Borhan, B. "Conformational Preference in Bis(porphyrin) Tweezer Complexes: A Versatile Chirality Sensor for -Chiral Carboxylic Acids", Eur. J. Org. Chem. 2012, 12, 3261-3269.
  30. Lee, K. S. S.; Berbasova, T.; Vasileiou, C.; Jia, X.; Wang,W.; Choi, Y.; Nossoni,F.; Geiger, J.; Borhan, B. "Probing Wavelength Regulation with an Engineered Rhodopsin Mimic and a C15-Retinal Analogue", ChemPlusChem 2012, 77(4), 273-276.
  31. Ashtekar, K. D.; Staples, R. J.; Borhan, B. "Development of a Formal Catalytic Asymmetric [4+2] Addition of Ethyl-2,3-butadienoate with Acyclic Enones",Org. Lett. 2011, 13, 5732-5735.
  32. Kulshrestha, A.; Schomaker, J. M.; Holmes, D.; Staples, R. J.; Jackson, J. E.; Borhan, B. "Selectivity in the Addition Reactions of Organometallic Reagents to Aziridine-2-carboxaldehydes: The Effects of Protecting Groups and Substitution Patterns",Chem. Eur. J. 2011, 17(44), 12326-12339.
  33. Hart, S. R.; Whitehead, D. C.; Travis, B.; Borhan, B. "Catalytic Oxidative Cleavage of Olefins Promoted by Osmium Tetroxide and Hydrogen Peroxide", Org. Biomol. Chem. 2011, 9, 4741-4744.
  34. Whitehead, D. C.; Fhaner, M.; Borhan, B. "A Peptide Bromoiodinane Approach for Asymmetric Bromolactonization", Tet. Lett. 2011, 52, 2288-2291.
  35. Jaganathan, A.; Garzan, A.; Whitehead, D. C.; Staples, R. J.; Borhan, B. "A Catalytic Asymmetric Chlorocyclization of Unsaturated Amides", Ang. Chem. Int. Ed. 2011, 50, 2593-2596.
  36. Yousefi, R.; Whitehead, D. C.; Mueller, J. M.; Staples, R. J.; Borhan, B. "On the Chlorenium Source in the Asymmetric Chlorolactonization Reaction", Org. Lett. 2011, 13(4), 608-611.
  37. Yan, J.; Garzan, A.; Narayan, R.; Vasileiou, C.; Borhan, B. "A minimalist approach for the structural revision of mucoxin", Chem. Eur. J. 2010, 16(46), 13749-13756.
  38. Acin-Perez R.; Hoyos, B.; Gong, J. L.; Vinogradov, V.; Fischman, D. A.; Leitges, M.; Borhan, B.; Starkov, A.; Manfredi, G.; Hammerling, U. "Regulation of intermediary metabolism by the PKC delta signalosome in mitochondria", FASEB J. 2010, 24(12), 5033-5042.
  39. Zhou, X.; Lu, Y.; Wang, W.; Borhan, B.; Reid, G. E. "Fixed Charge Chemical Derivatization and Data Dependant Multistage Tandem Mass Spectrometry for Mapping Protein Surface Residue Accessibility", J. Am. Soc. Mass Spec. 2010, 21(8), 1339-1351.
  40. Schaefer, L.; Auchtung, T. A.; Hermans, K. E.; Whitehead, D.; Borhan, B.; Britton, R. A. "The antimicrobial compound reuterin (3-hydroxypropion aldehyde) induces oxidative stress via interaction with thiol groups", Microbiology-SMG 2010, 156, 1589-1599.
  41. El-Boubbou, K.; Zhu, D. C.; Vasileiou, C.; Borhan, B.; Davide, P.; Wei, L.; Huang, X. "Magnetic glyco-nanoparticles: a tool to detect, differentiate, and unlock the glyco-codes of cancer via magnetic resonance imaging", J. Am. Chem. Soc. 2010, 132(12), 4490-4499.
  42. Whitehead, D. C.; Yousefi, R.; Jaganathan, A.; Borhan, B. "An organocatalytic asymmetric chlorolactonization", J. Am. Chem. Soc. 2010, 132(10), 3298-3300.
  43. Vasileiou, C.; Wang, W.; Jia, X.; Lee, K. S. S.; Watson, C.; Geiger, J.; Borhan, B. "Elucidating the exact role of engineered CRABPII residues for the formation of a retinal protonated Schiff base", Proteins: Structure, Function and Bioinformatics 2009, 77(4), 812-822.
  44. Tanasova, M.; Yang, Q.; Olmsted, C.C.; Vasileiou, C.; Li, X.; Anyika, M.; Borhan, B. "An Unusual Conformation of alpha-Haloamides due to Cooperative binding with zincated pophyrins", Eur. J. Org. Chem. 2009, 25, 4242-4253.
  45. Vasileiou, C.; Lee, K. S. S.; Crist, R. M.; Vaezeslami, S.; Goins, S. M.; Geiger, J. H.; Borhan, B. "Dissection of the critical binding determinants of cellular retinoic acid binding protein II by mutagenesis and fluorescence quenching", Proteins: Structure, Function and Bioinformatics 2009, 76(2), 281-290.
  46. Tanasova, M.; Vasileiou, C.; Olumolade, O. O.; Borhan, B. "Enhancement of exciton coupled circular dichroism with sterically encumbered bis-porphyrin tweezers", Chirality 2009, 21, 374-382.
  47. Whitehead, D. C.; Staples, R. J.; Borhan, B. "A simple and expedient method for the preparation of N-chlorohydantoins", Tet. Lett. 2009, 50(6), 656-658.
  48. Lu, Y. L.; Tanasova, M.; Borhan, B.; Reid, G. E. "Ionic reagent for controlling the gas-phase fragmentation reactions of cross-linked peptides", Anal. Chem. 2008, 80(23), 9279-9287.
  49. Li, X.; Borhan, B. "Prompt determination of absolute configuration for epoxy alcohols via exciton chirality protocol", J. Am. Chem. Soc. 2008, 130(48), 16126-16127.
  50. Vaezeslami, S.; Jia, X.; Vasileiou, C.; Borhan, B.; Geiger, J. H. "Structural analysis of site-directed mutants of cellular retinoic acid-binding protein II addresses the relatioship between structural integrity and ligand binding", Act. Cryst. Sec. D - Biol. Cryst. 2008, 64, 1228-1239.
  51. Schomaker, J. M.; Borhan, B. "Total synthesis of haterumalides NA and NC via a chromium-mediated macrocyclization", J. Am. Chem. Soc. 2008, 130(37), 12228-12229.
  52. Li, X.; Tanasova, M.; Vasileiou, C.; Borhan, B. "Fluorinated porphyrin tweezer: A powerful reporter of absolute configuration for erythro and threo diols, amino alcohols and diamines", J. Am. Chem. Soc. 2008, 130(6), 1885-1893.
  53. Vasileiou, C.; Vaezeslami, S.; Crist, R. M.; Rabago-Smith, M.; Geiger, J. H.; Borhan, B. "Protein Design: Reengineering cellular retinoic acid binding protein II into a rhodopsin protein mimic", J. Am. Chem. Soc. 2007, 129(19), 6140-6148.
  54. Schomaker, J. M.; Geiser, A. R.; Huang, R.; Borhan, B. "Tetrasubstituted pyrrolidines via a substituted aza-Payne/hydroamination reaction", J. Am. Chem. Soc. 2007, 129(13), 3794-3795.
  55. Schomaker, J. M.; Bhattacharjee, S.; Yan, J.; Borhan, B. "Diastereomerically and enantiomerically pure 2,3-disubstituted pyrrolidines from 2,3-aziridin-1-ols using a sulfoxonium ylide: A one-carbon homologative relay ring expansion", J. Am. Chem. Soc. 2007, 129(7), 1996-2003.
  56. Vaezeslami, S.; Mathes, E.; Vasileiou, C.; Borhan, B.; Geiger, J. H. "The structure of apo-wild-type cellular retinoic acid binding protein II at 1.4 A and its relationship to ligand binding and nuclear translocation", J. Mol. Biol. 2006, 363(3), 687-701.
  57. Whitehead, D. C.; Travis, B. R.; Borhan, B. "The OsO4-mediated oxidative cleavage of olefins catalyzed by alternative osmium sources", Tet. Lett. 2006, 47(22), 3797-3800.
  58. Crist, R. M; Vasileiou, C.; Rabago-Smith, M.; Geiger, J. H.; Borhan, B. "Engineering a rhodopsin protein mimic", J. Am. Chem. Soc. 2006, 128(14), 4522-4523.
  59. Karnaukhova, E.; Vasileiou, C.; Wang, A.; Berova, N.; Nakanishi, K.; Borhan, B. "Circular dichroism of heterochromophoric and partially regenerated purple membrane: Search for exciton coupling", Chirality 2006, 18(2), 72-83.
  60. Narayan, R. S.; Borhan, B. "Synthesis of the proposed structure of mucoxin via regio- and stereoselective tetrahydrofuran ring-forming strategies", J. Org. Chem. 2006, 71(4), 1416-1429.
  61. Horrigan, D. M.; Tetreault, M. L.; Tsomaia, N.; Vasileiou, C.; Borhan, B.; Mierke, D. F.; Crouch, R. K.; Zimmerman, A. L. "Defining the retinoid binding site in the rod cyclic nucleotide-gated channel", J. Gen. Physiol. 2005, 126(5), 453-460.
  62. Yang, Q. F.; Streb, K. K.; Borhan, B. "Polymer-supported synthesis of mono-substituted porphyrins", Tet. Lett. 2005, 46(39), 6737-6740.
  63. Zheng, T.; Narayan, R. S.; Schomaker, J. M.; Borhan, B. "One-pot regio- and stereoselective cyclization of 1,2,n-triols", J. Am. Chem. Soc. 2005, 127(19), 6946-6947.
  64. Yan, J.; Travis, B. R.; Borhan, B. "Direct oxidative cleavage of alpha- and beta- dicarbonyls and alpha-hydroxyketones to diesters with KHSO5", J. Org. Chem. 2004, 69(26), 9299-9302.
  65. Schomaker, J. M.; Pulgam, V. R.; Borhan, B. "Synthesis of diastereomerically and enantiomerically pure 2,3-disubstituted tetrahydrofurans using a sulfoxonium ylide", J. Am. Chem. Soc. 2004, 126(42), 13600-13601.
  66. Schomaker, J. M.; Borhan, B. "Total synthesis of (+)-tanikolide via oxidative lactonization", Org. Biomol. Chem. 2004, 2(4), 621-624.
  67. Schomaker, J. M.; Travis, B. R.; Borhan, B. "Direct lactonization of alkenols via osmium tetroxide-mediated oxidative cleavage", Org. Lett. 2003, 5(17), 3089-3092.
  68. Sivakumar, M.; Borhan, B. "Regiochemical control in intramolecular cyclization of 2,3-epoxysulfides mediated by solvent effects", Tet. Lett. 2003, 44(29), 5547-5551.
  69. Travis, B. R.; Sivakumar, M.; Hollist, G. O.; Borhan, B. "Facile Oxidation of aldehydes to acids and esters with oxone", Org. Lett. 2003, 5(7), 1031-1034.
  70. Travis, B. R.; Ciaramitaro, B. P.; Borhan, B. "Preparation of purified KHSO5.H2O and nBu4NHSO5 from oxone by simple and efficient methods", Eur. J. Org. Chem. 2002, 20, 3429-3434.
  71. Yang, Q.; Olmsted, C.; Borhan, B. "Absolute determination of chiral carboxylic acids", Org. Lett. 2002, 4(20), 3423-3426.
  72. Reddy, P. V.; Borhan, B. "Synthesis of C15,C14'-ring locked all-trans-beta-carotene", Tet. Lett. 2002, 43(21), 3867-3869.
  73. Travis, B. R.; Narayan, R. S.; Borhan, B. "Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: An organometallic ozonolysis", J. Am. Chem. Soc. 2002, 124(15), 3824-3825.
  74. Reddy, P. V.; Rabago-Smith, M.; Borhan, B. "Synthesis of all-trans-[10'-H-3]-8'-apo-beta-carotenoic acid", J. Labelled Comp. Radiopharm. 2002, 45(1), 79-89.
  75. Travis, B. R.; Borhan, B. "Oxidative cyclization of 1,4-dienes to yield 2,3,5-trisubstituted tetrahydrofuran-diols", Tet. Lett. 2001, 42(44), 7741-7745.
  76. Narayan, R. S.; Sivakumar, M.; Bouhlel, E.; Borhan, B. "Regiochemical control in intramolecular cyclization of methylene-interrupted epoxydiols", Org. Lett. 2001, 3(16), 2489-2492.
  77. Crist, R. M.; Reddy, P. V.; Borhan, B. "Synthesis of isomeric 1,4-[C-13](2)-labeled 2-ethoxycarbonyl-1,4-diphenylbutadienes", Tet. Lett. 2001, 42(4), 619-621.