Koide Group

Smith, S.E., Williams, J.M. & Koide, K. Time-insensitive fluorescent sensor for human serum albumin and its unusual red shift. Anal. Chem. 2014, 86, 2332–2336.

Williams, J.M. & Koide, K. A high-throughput method to detect palladium in ores. Ind. Eng. Chem. Res. 2013, 52, 8612–8615.

Gao, Y. & Koide, K. Chemical perturbation of Mcl-1 pre-mRNA splicing to induce apoptosis in cancer cells. ACS Chem. Biol. 2013, 8, 895–900.

Bu, X., Koide, K, Carder, E.J. & Welch, C.J. Rapid analysis of residual palladium in pharmaceutical development using a catalysis-based fluorometric method. Org. Process Res. Dev. 2013, 17, 108–113.

Gao, Y., Vogt, A, Forsyth, C.J., & Koide, K. Comparison of splicing factor 3b inhibitors in human cells. ChemBioChem 2013, 14, 49–52.

Osman, S. & Koide, K. Ruthenium-catalyzed olefin metathesis after tetra-n-butylammonium fluoride-mediated desilylation.Tetrahedron Lett. 2012, 53, 6637–6640.

Visconte, V., Rogers, H.J., Singh, J., Barnard, J., Bupathi, M., Traina, F., McMahon, J., Hakishima, H., Szpurka, H., Jankowska, A., Jerez, A., Sekeres, M.A., Sauntharajah, Y., Advani, A.S., Copelan, E., Koseki, H., Isono, K., Padgett, R.A., Osman, S., Koide, K, O’Keefe, C., Maciekewski, J.P. & Tiu, R.V. SF3B1 haploinsufficiency leads to formation of ring sideroblasts in myelodysplastic syndromes. Blood 2012, 120, 3173–3186.

Cook, M.P., Ando, S., & Koide, K. One-step synthesis of a fluorescein derivative and mechanistic studies” M. P. Cook, S. Ando, and K. Koide, Tetrahedron Lett. 2012, 53, 5284–5286.

Imamoto, K., Campbell, L.D., Doi, T. & Koide, K. A highly sensitive fluorescence method reveals the presence of palladium in a cross-coupling reaction mixture not treated with transition metals. L. D. Tetrahedron Lett. 2012, 53, 3147–3148.

Li, D., Campbell, L.D., Austin, B.A. & Koide, K. Detection of trace palladium in flasks and metal reagents using a fluorogenic Tsuji-Trost reaction. ChemPlusChem 2012, 77, 281–283.

Leslie, A.K., Li, D. & Koide, K. Amine-promoted β-elimination of a β-aryloxy aldehyde for fluorogenic chemodosimeters. J. Org. Chem. 2011, 76, 6860–6865.

Koide, K., Osman, S., Garner, A.L., Song, F., Dixon, T., Geenberger, J.S., & Epperly, M.W. The use of 3,5,4′-tri-O-acetylresveratrol as a potential pro-drug for resveratrol protects mice from γ-irradiation-induced death” ACS Med. Chem. Lett. 2011, 2, 270–274.

• One More Reason to Guzzle Red Wine (Newsweek Magazine May 23 & 30, 2011 issue)

Ando, S., Grote, A.L. & Koide, K. Diastereoselective synthesis of diketopiperazine bis-α,β-epoxides” S. Ando, A. L. Grote, and K. Koide, J. Org. Chem. 2011, 76, 1155–1158.

Ando, S. & Koide, K.  Development and applications of fluorogenic probes for mercury(II) based on vinyl ether oxymercuration. J. Am. Chem. Soc. 2011, 133, 2556–2566.

Osman, S., Albert, B.J., Wang, Y., Li, M. Czaicki, N.L., & Koide K. Structural requirements for the antiproliferative activity of pre-mRNA splicing inhibitor FR901464.Chem.-Eur. J. 2011, 17, 895–904.

Osman, S., Waud, W.R., Gorman, G.S., Day, B.W. & Koide, K. Evaluation of FR901464 analogues in vitro and in vivo. Med. Chem. Commun. 2011, 2, 38–43.

Song, F., Carder, E.J., Kohler, C.C. & Koide, K. Studies toward an ideal fluorescence method to measure palladium in functionalized organic molecules: effects of sodium borohydride, temperature, phosphine ligand, and phosphate ions on kinetics. Chem.-Eur. J. 2010, 16, 13500–13508.

Albert, B.J., McPherson, P.A., O’Brien, K., Czaicki, N.L., DeStefino, V., Osman, S., Li, M., Day, B.W., Grabowski, P.J., Moore, M., Vogt, A. & Koide, K. Meayamycin inhibits pre-mRNA splicing and exhibits picomolar activity against multidrug resistant cells. Mol. Cancer Ther. 2009, 8, 2308–2318. 

Garner, A.L., St. Croix, C.M., Pitt, B.R., Leikauf, G.D., Ando, S. & Koide, K. Specific fluorogenic probes for ozone in biological and atmospheric samples. Nature Chem. 2009, 1, 316–321.

• New probe promises ozone answers (Chemistry World)
  Pitt chemist is developing a bright idea (Pittsburgh Post-Gazette)
  News in brief (Nature Methods)

Garner, A.L., Song, F. & Koide, K. Enhancement of a catalysis-based fluorometric detection method for palladium through rational fine-tuning of the palladium species. J. Am. Chem. Soc. 2009, 131, 5163–5171.

• Green Chemistry

Uchida, T., Mills, K.L., Kuo, C.-H., Roh, W., Tung, Y.-C., Garner, A.L., Koide, K., Thouless, M.D. & Takayama, S. External compression-induced fracture patterning on the surface of poly(dimethylsiloxane) cubes and microspheres. Langmuir 2009, 25, 3102–3107.

Garner, A.L. & Koide, K. Studies of a fluorogenic probe for palladium and platinum leading to a palladium-specific detection method. Chem. Commun. 2009, 86–88.

Garner, A.L. & Koide, K. Fluorescent method for platinum detection in buffers and serums for cancer medicine and occupational hazards. Chem. Commun. 2009, 83–85.

Song, F., Watanabe, S., Floreancig, P.E. & Koide, K. Oxidation-resistant fluorogenic probe for mercury based on alkyne oxymercuration. J. Am. Chem. Soc. 2008, 130, 16460–16461.

Garner, A.L & Koide, K. Oxidation state-specific fluorescent method for palladium(II) and platinum(IV) based on the catalyzed aromatic Claisen rearrangement. J. Am. Chem. Soc. 2008, 130, 16472–16473. 

Osman, S. & Koide, K. Cyclic acetal formation between 2-pyridinecarboxaldehyde and γ-hydroxy-α,β-acetylenic esters.Tetrahedron Lett. 2008, 49, 6550–6552.

Koide, K., Song, F., de Groh, E.D., Garner, A.L., Mitchell, V.D., Davidson, L.A. & Hukriede, N.A. Scalable and concise synthesis of dichlorofluorescein derivatives displaying tissue permeation in live zebrafish embryos. ChemBioChem 2008, 9, 214–218.

Albert, B.J. & Koide, K. Zirconium-promoted epoxy rearrangement-alkynylation sequence” B. J. Albert, K. Koide, J. Org. Chem. 2008, 73, 1093–1098.

• Best Synthetic Methods: Carbon-Carbon Bond Construction

Garner, A.L. & Koide, K. Solid-phase olefin cross-metathesis promoted by a linker” A. L. Garner, K. Koide, Org. Lett. 2007, 9, 5235–5238.

• C&E News

Koide, K. Synthesis and biological activity of antitumor natural product FR901464 and its analogue” K. Koide, Farumashia 2007, 43, 1183–1188.

Albert, B.J. & Koide, K. How rapidly do epoxides non-specifically form covalent bonds with thiols in water?ChemBioChem 2007, 8, 1912–1915

• Cover page

Song, F., Garner, A.L. & Koide, K. A highly sensitive fluorescent sensor for palladium based on the allylic oxidative insertion mechanism. J. Am. Chem. Soc. 2007,129, 12354–12355.

• C&E News

Sparano, B.A. & Koide, K. Fluorescent sensors for specific RNA: A general paradigm using chemistry and combinatorial biology. J. Am. Chem. Soc. 2007,129, 4785–4794.

Sonye, J.P. & Koide, K. Sodium bicarbonate-catalyzed stereoselective isomerizations of electron-deficient propargylic alcohols to (Z)-enones. J. Org. Chem. 2007, 72. 1846–1848.

Albert, B.J., Sivaramakrishnan, A., Naka, T., Czaicki, N.L. & Koide, K. Total synthesis, fragmentation studies, and antitumor/antiproliferative activities of FR901464 and its low picomolar analogue. J. Am. Chem. Soc. 2007, 129. 2648–2659.

• This article was highlighted on the National Public Radio, in Nature, Pitt Chronicle, The Pitt News, The Carnegie Mellon University Tartan, Insider R&D, BioSpace, United Press International, Medilexicon

Koide, K. & Alpert, B.J., Review: Total syntheses of FR901464. J. Synth. Org. Chem. Jpn. 2007, 65. 119–126

Koide, K. A new paradigm for the development of fluorescent RNA imaging technology using synthetic molecules. American Biotechnology Laboratory 2006, 24, 8–10

Sonye, J.P. & Koide, K. Base-catalyzed stereoselective isomerization of electron-deficient propargylic alcohols to E-enones”J. Org. Chem. 2006, 71. 6254–6257.

Albert, B.J., Sivaramkrishnan, A., Naka, T. & Koide, K. Total synthesis of FR901464, an antitumor agent that regulates the transcription of oncogenes and tumor suppressor genes. J. Am. Chem. Soc. 2006, 128. 2792–2793.

Sonye, J.P. & Koide, K. Organic base-catalyzed stereoselective isomerizations of 4-hydroxy-4-phenyl-but-2-ynoic acid methyl ester to (E)- and (Z)-4-oxo-4-phenyl-but-2-enoic acid methyl esters. Synth. Commun. 2006, 36, 599–602.

Sonye, J.P. & Koide, K. On the mechanism of DABCO-catalyzed stereoselective isomerization of g-hydroxy-a,b-alkynoates to gamma-oxo-alpha,beta-(E)-alkenoates” Org. Lett. 2006, 8, 199–202. 

Sparano, B.A. & Koide, K. A strategy for the development of small molecule-based sensors that strongly fluoresce when bound to a specific RNA. J. Am. Chem. Soc. 2005, 127, 14954–14955.

• (Ranked 6th in the “Most-Accessed Articles: October-December, 2005” list)

Albert, B.J. & Koide, K. Synthesis of a C4-epi C1-C6 fragment of FR901464 using a novel bromolactolization. Org. Lett. 2004, 6, 3655–3658.

Sparano, B.A., Shahi, S.P. & Koide, K. Effect of binding and conformation on fluorescence quenching in new 2′,7′-dichlorofluorescein derivatives. Org. Lett., 2004, 6, 1947–1949. 

Meta, C.T. & Koide, K. Trans-selective conversions of gamma-hydroxy-alpha,beta-alkynoic esters to g-hydroxy-a,b-alkenoic esters. Org. Lett. 2004, 6, 1785–1787.

Shahi, S.P. & Koide, K. A mild method for the preparation of gamma-hydroxy-alpha,beta-acetylenic esters. Angew. Chem. Int. Ed. 2004, 43, 2525–2527.

Naka, T. & Koide, K. A novel and simple method to prepare g-hydroxy-a,b-(E)-alkenoic esters from g-keto-alkynoic esters.Tetrahedron Lett. 2003, 44, 443–445.

Graduate and Postdoctoral Work (1-15):

Koide, K., Finkelstein, J.M., Ball, Z. & Verdine, G.L. A synthetic library of cell-permeable molecules. J. Am. Chem. Soc. 2001, 123, 398.

Setyawan, J., Koide, K., Diller, T.C., Bunnage, M.E., Taylor, S.S., Nicolaou, K.C. & Brunton, L.L. Inhibition of protein kinases by balanol: Specificity within the serine/threonine protein kinase sub-family”, Mol. Pharm. 1999, 56, 370.

Narayana, N., Diller, T.C., Koide, K., Munnage, M.E., Nicolaou, K.C., Brunton, L.L., Xuong, N.-H., Ten Eyck Ten, L.F., & S.S. Taylor. Crystal structure of the potent natural product inhibitor balanol in complex with the catalytic subunit of cAMP-dependent protein kinase. Biochemistry 1999, 38, 2367.

Furukawa, H., Koide, K., Takao, & Kobayashi, S. Glycosyl 2-pyridinecarboxylate as an effective glycosyl donor: Glycosidation of mannose, 2-azidosugar, and 2-deoxysugar into disaccarides. Chem. Pharm. Bull. 1998, 46, 1244.

Nicolaou, K.C., Koide, K., Xu, J. & Izraelwicz, M.H. Synthetic studies on maduropeptin chromophore.  2.  Synthesis of the madurosamine aryl amide and the C1′-C9′ fragments.Tetrahedron Lett. 1997, 38, 3671.

Nicolaou, K.C., Koide, K., Khatuya, H. Synthetic studies on maduropeptin chromophore. 1. Construction of the aryl ether and attempted synthesis of the [7.3.0] bicyclic system.Tetrahedron Lett. 1997, 38, 3667.

Koide, K., Ohno, M., Kobayashi, S. Glycosyl fluoride for glycosidation promoted by a catalytic amount of gallium reagent. Synthesis 1996, 1175.

Koide, K., Bunnage, M.E., Gomez Paloma, L., Kanter, J.R., Taylor, S.S., Brunton, L.L. & Nicolaou K.C. Molecular design and biological activity of potent and selective protein kinase inhibitors related to balanol.Chem. Biol. 1995, 2, 601.

Nicolaou, K.C., Koide, K., & Bunnage, M.E. Total synthesis of balanol and designed analogues. Chem. Eur. J. 1995, 1, 454.

Nicolaou, K.C., Piscopio, A.D., Bertinato, P., Minowa, N., Chakraborty, T.K. & Koide, K. Total synthesis of rapamycin. Chem. Eur. J. 1995, 1, 316.

Nicolaou, K.C., Tiebes, J., Theodorakis, E.A., Rutjes, F.P.J.T., Koide, K., Sato, M. & Unterstellar, E. Total synthesis of truncated brevetoxin B [AFGHIJK]. J. Am. Chem. Soc. 1994, 116, 9371.

Nicolaou, K.C., Bunnage, M.E., Koide, K. Total synthesis of balanol. K. Koide, J. Am. Chem. Soc.1994, 116, 8402.

Piscopio, A.D., Minowa, N., Chakraborty, T.K., Koide, K., Bertinato, P. & Nicolaou, K.C. A highly convergent strategy towards rapamycin. Stereoselective construction of the C8-C18 fragment. J. Chem. Soc. Chem. Commun. 1993, 7, 617.

Koide, K., Ohno, M., & Kobayashi, S. A new glycosylation reaction based on a remote activation concept – Glycosyl 2-pyridinecarboxylate as a novel glycosyl donor. Tetrahedron Lett. 1991, 32, 7065.

Kobayashi, S., Koide, K. & Ohno, M. Gallium reagents in organic synthesis: Dimethylgallium chloride and triflate as activators in glycosidation using glycopyranosyl fluorides.Tetrahedron Lett. 1990, 31, 2435.