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Kemin Wang - One of the best experts on this subject based on the ideXlab platform.

  • dna Tetrahedron nanostructures for biological applications biosensors and drug delivery
    Analyst, 2017
    Co-Authors: Nuli Xie, Xiaohai Yang, Jin Huang, Shiyuan Liu, Kemin Wang
    Abstract:

    With the rapid development of DNA nanotechnology, various DNA nanostructures with different shapes and sizes have been self-assembled using “bottom-up” fabrication strategies and applied to a wide range of fields such as biosensors, drug delivery and tools for molecular biology. As a classical and simple polyhedron, DNA Tetrahedron can be easily synthesised by a one-step assembly. Due to the excellent biocompatibility and cellular permeability, it provides a universal and promising platform to construct a series of biosensors and drug delivery systems for living cells studies. Moreover, the high programmability of DNA Tetrahedron determines its capability to perform artful design and combine with other materials. Herein, we review and summarise the development and applications of DNA Tetrahedron in living cell studies. We mainly focus on two parts, cellular biosensors for the detection of nucleic acids, proteins, small molecules and cancer cells and drug delivery systems for chemotherapy, immunotherapy, photodynamic therapy and gene silencing. With the rapid progress in DNA Tetrahedron as well as DNA nanotechnology, new avenues and opportunities have opened up in analytical chemistry, molecular biology and medicine.

  • a dna Tetrahedron based molecular beacon for tumor related mrna detection in living cells
    Chemical Communications, 2016
    Co-Authors: Nuli Xie, Xiaohai Yang, Jin Huang, Yanjing Yang, Ke Quan, He Wang, Le Ying, Kemin Wang
    Abstract:

    Due to its low cytotoxicity, high resistance to enzymatic degradation, and cellular permeability, a DNA Tetrahedron-based molecular beacon (DTMB) is designed for tumor-related TK1 mRNA detection in living cells, where the target sequence can induce the Tetrahedron from contraction to extension, resulting in fluorescence restoration.

Simone Speziale - One of the best experts on this subject based on the ideXlab platform.

  • a semiclassical Tetrahedron
    Classical and Quantum Gravity, 2006
    Co-Authors: Carlo Rovelli, Simone Speziale
    Abstract:

    We construct a macroscopic semiclassical state for a quantum Tetrahedron. The expectation values of the geometrical operators representing the volume, areas and dihedral angles are peaked around assigned classical values, with vanishing relative uncertainties.

  • a semiclassical Tetrahedron
    arXiv: General Relativity and Quantum Cosmology, 2006
    Co-Authors: Carlo Rovelli, Simone Speziale
    Abstract:

    We construct a macroscopic semiclassical state state for a quantum Tetrahedron. The expectation values of the geometrical operators representing the volume, areas and dihedral angles are peaked around assigned classical values, with vanishing relative uncertainties.

Coelho F. - One of the best experts on this subject based on the ideXlab platform.

  • First Comprehensive Bakkane Approach: Stereoselective And Efficient Dichloroketene-based Total Syntheses Of (±)- And (-)-9-acetoxyfukinanolide, (±)- And (+)-bakkenolide A, (-)-bakkenolides Iii, B, C, H, L, V, And X, (±)- And (-)-homogynolide A, (±)-h
    2015
    Co-Authors: Brocksom T.j., Coelho F., Depres J.-p., Greene A.e., Freire De Lima M.e., Hamelin O., Hartmann B., Kanazawa A.m., Wang Y.
    Abstract:

    Cycloaddition of dichloroketene with dimethylcyclohexenes has been used as the key reaction in an efficient, general approach to the bakkanes. New methods and methodologies that have been developed in this work include spiro β-methylene-γ-butyrolactonizations, a vicinal dicarboxylation, an angelic ester preparation, a transesterification, an epoxy ketone double reduction, and a retro aldol-aldol approach to low-energy aldol isomers.124511531315325Fischer, N.H., Oliver, E.J., Fischer, H.D., (1979) Progress in the Chemistry of Organic Natural Products, 38. , Herz, W., Grisebach, H., Kirby, G. W., Eds.Springer-Verlag: New YorkChapter 2Silva L.F., Jr., (2001) Synthesis, pp. 671-689noteAbe, N., Onoda, R., Shirahata, K., Kato, T., Woods, M.C., Kitahara, Y., (1968) Tetrahedron Lett., 9, pp. 369-373Shirahata, K., Kato, T., Kitahara, Y., Abe, N., (1969) Tetrahedron, 25, pp. 3179-3191Naya, K., Takagi, I., Hayashi, M., Nakamura, S., Kobayashi, M., Katsumura, S., (1968) Chem. Ind. 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Chem., 50, pp. 3943-3945. , ±-bakkenolide AGreene, A.E., Coelho, F., Deprés, J.-P., Brocksom, T.J., (1988) Tetrahedron Lett., 29, pp. 5661-5662. , +-bakkenolide ACoelho, F., Deprés, J.-P., Brocksom, T.J., Greene, A.E., (1989) Tetrahedron Lett., 30, pp. 565-566. , ±-homogynolide BHartmann, B., Kanazawa, A.M., Deprés, J.-P., Greene, A.E., (1991) Tetrahedron Lett., 32, pp. 767-768. , ±-homogynolide AHartmann, B., Kanazawa, A.M., Deprés, J.-P., Greene, A.E., (1993) Tetrahedron Lett., 34, pp. 3875-3876. , --homogynolide AHartmann, B., Deprés, J.-P., Greene, A.E., Freire de Lima, M.E., (1993) Tetrahedron Lett., 34, pp. 1487-1490. , ±-palmosalide CHamelin, O., Deprés, J.-P., Greene, A.E., Tinant, B., Declercq, J.-P., (1996) J. Am. Chem. Soc., 118, pp. 9992-9993. , ±-9-acetoxyfukinanolideHamelin, O., Deprés, J.-P., Heidenhain, S., Greene, A.E., (1997) Nat. Prod. Lett., 10, pp. 99-103. , --9-acetoxyfukinanolideHamelin, O., Wang, Y., Deprés, J.-P., Greene, A.E., (2000) Angew. Chem. Int. 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  • Piperonal As Electrophile In The Baylis-hillman Reaction. A Synthesis Of Hydroxy-β-piperonyl-γ-butyrolactone Derivative
    2015
    Co-Authors: Almeida W.p., Coelho F.
    Abstract:

    Aromatic aldehydes are reluctant to serve as substrates for the Baylis- Hillman reaction at all under the relatively mild conditions. In our research, we have achieved that piperonal could be an useful substrate in this reaction, employing ultrasound technique. The adduct obtained was used in the preparation of key intermediates for the total synthesis of hydroxylated lignans.394786098612Basavaiah, D., Rao, P.D., Hyma, R.S., (1996) Tetrahedron, 52, p. 8001Drewes, S.E., Roos, G.H.P., (1988) Tetrahedron, 44, p. 4653Trost, B.M., (1983) Science, 219, p. 245Leahy, J.W., Rafel, S., Brzezinski, L.J., (1997) J. Am. Chem. Soc., 119, p. 4317Markó, I.E., Giles, P.R., Hindley, N.J., (1997) Tetrahedron, 53, p. 1015Gilbert, A., Heritage, T.W., Isaacs, N.S., (1991) Tetrahedron: Asymmetry, 2, p. 969. , and references thereinWard, R., (1997) S. Nat. Prod. Rep., p. 43noteForty, Y., Berthe, M.C., Caubere, P., (1992) Tetrahedron, 48, p. 6371White, J.D., Kuo, S.-C., Vedananda, T.R., (1987) Tetrahedron Lett., 28, p. 3061noteHeathcock, C.H., (1984) Asymmetric Synthesis, 3 (PART B), p. 115. , Morrison, J. D., Ed., Academic Press, LondonPerlmutter, P., Tabone, M., (1988) Tetrahedron Lett., 29, p. 949Drewes, S.E., Emslie, N.D., Field, J.S., Kahn, A.A., Ramesar, N., (1992) Tetrahedron: Asymmetry, 3, p. 25

  • Organocatalysis Reactions With Chiral Amines. Mechanistic Aspects And Use On Organic Synthesis [reações De Organocatálise Com Aminas Quirais. Aspectos Mecanísticos E Aplicações Em Síntese Orgânica]
    2015
    Co-Authors: Amarante G.w., Coelho F.
    Abstract:

    The philosophy of organocatalysis is based on the utilization of organic compounds to catalyze organic transformations without the intervention of metals. This area has attracted much attention of the synthetic chemistry community on the last years, which can be confirmed by the explosion of published papers dealing with this subject. Phosphorus compounds, urea and thiourea derivatives, alkaloids, guanidine derivatives, for example, have already been used as organocatalysts. In this review we have focused on the use of chiral amines as organocatalyst. We have also chosen some outstanding examples to demonstrate the potentiality of this strategy in the synthesis of natural products and biologically active compounds.322469481Alexakis, A., (2007) Chimia, 61, p. 212Hajos, Z.G., Parrish, D.R., (1974) J. Org. Chem, 39, p. 1615Hajos, Z. G.Parrish, D. R.Patente Alemã DE 2,102,623,1978 (CA, 1978, 88, 62529)Eder, U., Sauer, G., Wiechert, R., (1971) Angew. Chem., Int. 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  • Diastereoselectivity In Heterogeneous Catalytic Hydrogenation Of Baylis-hillman Adducts. Total Synthesis Of (±)-sitophilate
    2015
    Co-Authors: Mateus C.r., Coelho F., Feltrin M.p., Costa A.m., Almeida W.p.
    Abstract:

    We describe herein a highly diastereoselective total synthesis of racemic sitophilate, based on the results obtained in a diastereoselective heterogeneous catalytic hydrogenation reaction of a set of Baylis-Hillman adducts originating from aliphatic aldehydes. © 2001 Published by Elsevier Science Ltd.573269016908Baylis, A.B., Hillman, M.E.D., (1972) Chem. Abstr., 77, pp. 34174q. , German Patent 2155113, 1972Basavaiah, D., Rao, P.D., Hyma, R.S., (1996) Tetrahedron, 52, p. 8001Ciganek, E., (1997) Organic Reactions, 51, pp. 201-350. , John Wiley & Sons Inc.: New York, Chapter 2Almeida, W.P., Coelho, F., (2000) Quím. Nova, 23, p. 98. , (Chem. Abstr., 2000, 132, 236562e)Almeida, W.P., Coelho, F., (1998) Tetrahedron Lett., 39, p. 8609Almeida, W.P., Mateus, C.R., Coelho, F., (2000) Tetrahedron Lett., 41, p. 2533Masunari, A., Ishida, E., Trazzi, G., Almeida, W.P., Coelho, F., (2001) Synth. Commun., 31 (14), pp. 2127-2136Faustini, D.L., Giese, W.L., Phillips, J.K., Burkholder, W.E., (1982) J. Chem. Ecol., 8, p. 679Phillips, J.K., Miller, S.P.F., Andersen, J.F., Fales, H.M., Burkholder, W.E., (1987) Tetrahedron Lett., 28, p. 6145Monro, H.A.U., Upitis, E., Bond, E.J., (1972) J. Stored Prod. Res., 8, p. 199Lloyd, C.J., (1973) J. Stored Prod. Res., 9, p. 77Chong, J.M., (1989) Tetrahedron, 45, p. 623Mori, K., Ishikura, M., (1989) Liebigs Ann. Chem., p. 1263Cheskis, B.A., Moiseenkov, A.M., Shpiro, N.A., Stashina, G.A., Zhulin, V.M., (1990) Bull. Acad. Sci. USSR CH, 39, p. 716Cheskis, B.A., Shpiro, N.A., Moiseenkov, A.M., (1991) Bull. Acad. Sci. USSR CH, 40, p. 2205Sugai, T., Sakuma, D., Kobayashi, N., Ohta, H., (1991) Tetrahedron, 47, p. 7237Chu, K.-H., Zhen, W., Zhu, X.-Y., Rosenblum, M., (1992) Tetrahedron Lett., 33, p. 1173Gu, J.X., Zy, L., Lin, G.Q., (1993) Tetrahedron, 49, p. 386Gil, P., González, A., Razkin, J., (1996) Tetrahedron: Asymmetry, 7, p. 3479DiBattista, J.P., Webster, F.X., (1996) Bioorg. Med. Chem., 4, p. 423Gil, P., Razkin, J., González, A., (1998) Synthesis, p. 386Naik, D.G., Puntambekar, H.M., (1998) Synth. Commun., 28 (13), p. 2399Brown, J.M., Cutting, I., (1985) J. Chem. Soc., Chem. Commun., p. 578Brown, J.M., (1987) Angew. Chem., Int. Ed. Engl., 26, p. 190Brown, J.M., Cutting, I., James, A.P., (1988) Bull. Soc. Chim. Fr., p. 211Yamamoto, K., Takagi, M., Tsuji, J., (1988) Bull. Chem. Soc. Jpn., p. 319Brown, J.M., Rose, M., Knight, F.I., Wienand, A., (1995) Recl. Trav. Chim. Pays-Bas, 114, p. 247Brown, J.M., Evans, P.L., James, A.P., (1990) Org. Synth., 68, p. 64Farington, E., Franchini, M.C., Brown, J.M., (1998) Chem. Commun., p. 277Sato, S., Matsuda, I., Shibata, M., (1989) J. Organomet. Chem., 377, p. 347Hoffmman, H.M.R., Rabe, J., (1985) J. Org. Chem., 50, p. 3849Fort, Y., Berthe, M.C., Caubère, P., (1992) Tetrahedron, 48, p. 6371Corey, E.J., Venkateswalu, A., (1972) J. Am. Chem. Soc., 94, p. 6190Heathcock, C.H., (1984) Asymmetric Synthesis, 3 (PART B). , Morrison, J. D., Ed.Academic: LondonFelkin, H., Chérest, M., Prudent, N., (1968) Tetrahedron Lett., p. 2199Felkin, H., Chérest, M., (1968) Tetrahedron Lett., p. 2205Ahn, N.T., Eisenstein, O., (1977) Nouv. J. Chem., 1, p. 61Jackson, R.S.W., Standen, S.P., Clegg, W., McCamlevy, A., (1992) Tetrahedron Lett., 33, p. 619

  • The Baylis-hillman Reaction With Chiral α-amino Aldehydes Under Racemization-free Conditions
    2015
    Co-Authors: Coelho F., Diaz G., Abella C.a.m., Almeida W.p.
    Abstract:

    The Baylis-Hillman reaction with chiral α-amino aldehydes has been revisited. The reaction carried out under the influence of ultrasound avoids the aldehyde racemization almost completely, providing useful chiral substrates which can be used as starting materials for the synthesis of natural products. To demonstrate the synthetic applicability of these adducts, the easy preparation of a bicyclic lactam with an indolizidinic skeleton was accomplished. © Georg Thieme Verlag Stuttgart.3435439Basavaiah, D., Rao, A.J., Satyanarayama, T., (2003) Chem. Rev., 103, p. 811Almeida, W.P., Coelho, F., (2000) Quim. Nova, 23, p. 98(2000) Chem. Abstr., 132, pp. 236562eCiganek, E., (1997) Org. React., 51, p. 201Basavaiah, D., Rao, P.D., Hyma, R.S., (1996) Tetrahedron, 52, p. 8001Santos, L.S., Pavam, C.H., Almeida, W.P., Coelho, F., Eberlin, M.N., (2004) Angew. Chem. Int. Ed., 43, p. 4330Price, K.E., Broadwater, S.J., Walker, B.J., McQuade, D.T., (2005) J. Org. Chem., 70, p. 3980Aggarwal, V.K., Fulford, S.Y., Llyod-Jones, G.C., (2005) Angew. Chem. Int. Ed., 44, p. 1706Mateus, C.R., Coelho, F., (2005) J. Braz. Chem. Soc., 16, pp. 386-396. , http://jbcs.sbq.org.br/online/2005/vol16_n3A/11-238-04.pdfPorto, R.S., Coelho, F., (2004) Synth. Commun., 34, p. 3037Feltrin, M.A., Almeida, W.P., (2003) Synth. Commun., 33, p. 1141Rossi, R.C., Coelho, F., (2002) Tetrahedron Lett., 42, p. 2797Mateus, C.R., Feltrin, M.P., Costa, A.M., Coelho, F., Almeida, W.P., (2001) Tetrahedron, 57, p. 6901Iwabuchi, Y., Furukawa, M., Esumi, T., Hatakeyama, S., (2001) Chem. Commun., p. 2030Iwabuchi, Y., Sugihara, T., Esumi, T., Hatakeyama, S., (2001) Tetrahedron Lett., 42, p. 7867Masunari, A., Trazzi, G., Ishida, E., Coelho, F., Almeida, W.P., (2001) Synth. Commun., 31, p. 2100Roos, G., Manickum, T., (1991) Synth. Commun., 21, p. 2269Drewes, S.E., Khan, A.A., Rowland, K., (1993) Synth. Commun., 23, p. 183Ameer, F., Drewes, S.E., Houston-McMillan, M.S., Kaye, P.T.S., (1986) Afr. J. Chem., 39, p. 57(1986) Chem. Abstr., 105, p. 114809Manickum, T., Roos, G.H.P.S., (1994) Afr. J. Chem., 47, p. 1(1994) Chem. Abstr., 122, p. 159795Alcaide, B., Almendros, P., Aragoncillo, C., (2001) J. Org. Chem., 66, p. 1612Alcaide, B., Almendros, P., Aragoncillo, C., Rodríguez-Acebes, R., (2004) J. Org. Chem., 69, p. 826. , and references cited thereinNayak, S.K., Thijs, L., Zwanenburg, B., (1999) Tetrahedron Lett., 40, p. 981Haner, R., Olano, B., Seebach, D., (1987) Helv. Chim. Acta, 70, p. 1676Almeida, W.P., Coelho, F., (2003) Tetrahedron Lett., 44, p. 937Einhorn, J., Einhorn, C., Luche, J.-L., (1991) Synlett, p. 37Bodanszky, M., Bodanszky, A., (1994) The Practice of Peptide Synthesis, 2nd Ed., , Springer-Verlag: Berlin/HeidelbergYoshifuji, S., Tanaka, K., Kawai, T., Nitta, Y., (1986) Chem. Pharm. Bull., 34, p. 3873Esquerra, J., Pedregal, C., Rubio, A., Yruretagoyena, B., Escribano, A., Sanchez-Ferrando, F., (1993) Tetrahedron, 49, p. 8665Gobiowske, A., Jurczak, J., Jacobsson, U., (1987) Tetrahedron, 43, p. 3063Luly, J.R., Dellaria, J.F., Palttner, J.J., Soderquist, J.L., Yi, N., (1987) J. Org. Chem., 52, p. 1487Fehrentz, J.A., Castro, B., (1983) Synthesis, p. 676Saari, W.S., Fisher, T.E., (1990) Synthesis, p. 453Kemp, D.J., (1986) J. Org. Chem., p. 3921D'Aniello, F., Taddei, M., (1992) J. Org. Chem., 57, p. 5247Romo, D., Meyer, S.D., Johnson, D.D., Schreiber, S.L., (1993) J. Am. Chem. Soc., 115, p. 7906Myers, A.G., Zhong, B.Y., Movassaghi, M., Kung, D.W., Lanman, B.A., Kwon, S., (2000) Tetrahedron Lett., 41, p. 1359. , and references cited thereinSchuch, C.M., Pilli, R.A., (2000) Tetrahedron: Asymmetry, 11, p. 153Dias, L.C., Ferreira, A.A., Diaz, G., (2002) Synlett, p. 1845Dias, L.C., Meira, P.R.R., (2000) Synlett, p. 37Benedetti, F., Miertus, S., Norbedo, S., Tossi, A., Zlatoidzky, P., (1997) J. Org. Chem., 62, p. 9348Vara Prasad, J.V.N., Rich, D.H., (1991) Tetrahedron Lett., 32, p. 5857Cherest, M., Felkin, H., Prudent, N., (1968) Tetrahedron Lett., 18, p. 2199Ahn, N.T., (1980) Top. Curr. Chem., 88, p. 144Hoffmann, R.W., (1989) Chem. Rev., 89, p. 1841Muroni, D., Saba, A., Culeddu, N., (2004) Tetrahedron: Asymmetry, 15, p. 2609Dieter, R.K., Lu, K., (2002) J. Org. Chem., 67, p. 847Sibi, M.P., Christensen, J.W., (1999) J. Org. Chem., 64, p. 6434Lim, S.H., Ma, S., Beak, P., (2001) J. Org. Chem., 66, p. 9056Clive, D.L.J., Yu, M., Li, Z., (2005) Chem. Commun., p. 90

Correia C.r.d. - One of the best experts on this subject based on the ideXlab platform.

  • Highly Regio- And Stereoselective Heck Reaction Of Allylic Esters With Arenediazonium Salts: Application To The Synthesis Of Kavalactones
    2015
    Co-Authors: Moro A.v., Cardoso F.s.p., Correia C.r.d.
    Abstract:

    Image Presented A highly efficient palladium-catalyzed Heck reaction of allylic esters with arenediazonium salts is described. The reaction proceeds under mild conditions, with excellent to total regio- and stereochemical control and with retention of the traditional leaving group. Furthermore, the generality of the present methodology is illustrated by the short total synthesis of the natural kavalactones, yangonine, (±)-methysticin, and (±)-dihydromethysticin. © 2009 American Chemical Society.111636423645Beletskaya, I.P., Cheprakov, A.V., (2000) Chem. Rev, 100, p. 3009Alonso, F., Beletskaya, I.P., Yus, M., (2005) Tetrahedron, 61, p. 11771(2002) Handbook of Organopalladium Chemistry for Organic Synthesis, , Negishi, E.-I. Ed, Wiley-Interscience: New YorkTsuji, J., (2004) Palladium Reagents and Catalyst, , Wiley: Chichester, U.KCalò, V., Nacci, A., Monopoli, A., Ferola, V., (2007) J. Org. Chem, 72, p. 2596Bouquillon, S., Ganchegui, B., Estrine, B., Hénin, F., Muzart, J., (2001) J. Organomet. Chem, 634, p. 153Ambrogio, I., Cacchi, S., Fabrizi, G., Goggiamani, A., Sgalla, S., (2009) Synlett, p. 620Zawisza, A.M., Ganchegui, B., González, I., Bouquillon, S., Roglans, A., Hénin, F., Muzart, J., (2008) J. Mol. Catal. A: Chem, 283, p. 140Liu, S., Thomson, N., Pettman, A., Hyder, Z., Mo, J., Xiao, J., (2008) J. Mol. Catal. A: Chem, 279, p. 210Batt, F., Gozzi, C., Fache, F., (2008) Chem. Commun, p. 5830Scrivanti, A., Bertoldini, M., Beghetto, V., Matteoli, U., (2008) Tetrahedron, 64, p. 543Alacid, E., Nájera, C., (2007) Adv. Synth. Catal, 349, p. 2572Berthiol, F., Doucet, H., Santelli, M., (2005) Eur. J. Org. Chem, p. 1367Kang, S., Lee, H., Jang, S., Kim, T., Pyun, S., (1996) J. Org. Chem, 61, p. 2604Bernocchi, E., Cacchi, S., Ciattini, P.G., Morera, E., Ortar, G., (1992) Tetrahedron Lett, 33, p. 3073Ono, K., Fugami, K., Tanaka, S., Tamaru, Y., (1994) Tetrahedron Lett, 35, p. 4133Jeffery, T., (1991) Tetrahedron Lett, 32, p. 2121Masllorens, J., Bouquillon, S., Roglans, A., Hénin, F., Muzart, J., (2005) J. Organomet. Chem, 690, p. 3822Barbero, M., Cadamuro, S., Dughera, S., (2006) Synthesis, p. 3443Cacchi, S., Fabrizi, G., Goggiamani, A., Sferrazza, A., (2009) Synlett, p. 973Perez, R., Veronese, D., Coelho, F., Antunes, O.A.C., (2006) Tetrahedron Lett, 47, p. 1325Sengupta, S., Sadhukhan, S.K., (1998) Tetrahedron Lett, 39, p. 1237Trost, B.M., Van Vranken, D.L., (1996) Chem. Rev, 106, p. 395Pan, D., Chen, A., Su, Zhou, W., Li, S., Jia, W., Xiao, J., Jiao, N., (2008) Angew. Chem., Int. Ed, 47, p. 4729Mariampillai, B., Herse, C., Lautens, M., (2005) Org. Lett, 7, p. 4745. , For Heck arylations followed by -acetoxy elimination, see: aLautens, M., Tayama, E., Herse, C., (2005) J. Am. Chem. Soc, 127, p. 72Delcamp, J.H., White, M.C., (2006) J. Am. Chem. Soc, 128, p. 15076Su, Y., Jiao, N., (2009) Org. Lett, 11, p. 2980Aydin, J., Larsson, J.M., Selander, N., Szabó, K.J., (2009) Org. Lett, 11, p. 2852Bilia, A.R., Scalise, L., Bergonzi, M.C., Vincieri, F.F., (2004) J. Chromatogr. B, 812, p. 203Côté, C.S., Kor, C., Cohen, J., Auclair, K., (2004) Biochem. Biophys. Res. Commun, 322, p. 147Roglans, A., Pla-Quitana, A., Moreno-Manas, M., (2006) Chem. Rev, 106, p. 4622Severino, E.A., Costenaro, E.R., Garcia, A.L.L., Correia, C.R.D., (2003) Org. Lett, 5, p. 305Meira, P.R.R., Moro, A.V., Correia, C.R.D., (2007) Synthesis, p. 2279Burtoloso, A.C.B., Garcia, A.L.L., Miranda, K.C., Correia, C.R.D., (2006) Synlett, p. 3145Pastre, J.C., Correia, C.R.D., (2006) Org. Lett, 8, p. 1657da Silva, K.P., Godoi, M.N., Correia, C.R.D., (2007) Org. Lett, 9, p. 2815Gruber, A.S., Pozebon, D., Monteiro, A.L., Dupont, J., (2001) Tetrahedron Lett, 42, p. 7345. , For other Pd pre-catalysts operating under ligand-free conditions, seeMoro, A.V., Cardoso, F.S.P., Correia, C.R.D., (2008) Tetrahedron Lett, 49, p. 5668Amaral, P.A., Gouault, N., Le Roch, M., Eifler-Lima, V., David, M., (2008) Tetrahedron Lett, 49, p. 6607Hashimoto, T., Suganuma, M., Fujiki, H., Yamada, M., Kohno, T., Asakawa, Y., (2003) Phytomedicine, 10, p. 309Lygo, B., (1995) Tetrahedron, 51, p. 12859Scherer, J., (1998) Adv. Nat. Ther, 15, p. 261Bilia, A.R., Gallori, S., Vincieri, F.F., (2002) Life Sci, 70, p. 258

  • Differential Oxidation Of Endocyclic Enecarbamates. Synthesis Of Cyclic β-hydroxy-α-amino Acids
    2015
    Co-Authors: Sugisaki C.h., Carroll P.j., Correia C.r.d.
    Abstract:

    The differential oxidation of five and six-membered endocyclic enecarbamates was investigated employing m-CPBA, DMD, as well as enantioselectivc protocols such as the Kochi-Jacobsen-Katsuki's epoxidation and the Sharpless dihydroxylation. By this strategy the syntheses of β- hydroxyprolines and β-hydroxypipecolic acids were accomplished, X-Ray crystallographic analysis of the trans-β-hydroxypipecolic acid was instrumental to solve structural assignment conflicts.392134133416Hanessian, S., M-Smith, G., Lombart, H.-G., Lubell, W.D., (1997) Tetrahedron, 53, p. 12789Sharma, R., Lubell, W.D., (1996) J. Org. Chem., 61, p. 202Beausoleil, E., L'Archevêque, B., Bélec, L., Atfani, M., Lubell, W.D., (1996) J. Org. Chem., 61, p. 9447Mulzer, J., Meier, A., (1996) J. Org. Chem., 61, p. 566Herdeis, C., Hubmann, H.P., (1994) Tetrahedron Asymmetry, 5, p. 119Dieterich, P., Young, D.W., (1993) Tetrahedron Lett., 34, p. 5455Pohlit, A.M., Correia, C.R.D., (1997) Heterocycles, 45, p. 2321Carpes, M.J.S., Miranda, P.C.M.L., Correia, C.R.D., (1997) Tetrahedron Lett., 38, p. 1869Correia, C.R.D., Faria, A.R., Carvalho, E.S., (1995) Tetrahedron Lett., 36, p. 5109Faria, A.R., Matos, C.R., Correia, C.R.D., (1993) Tetrahedron Lett., 34, p. 27Williams, R.M., Cao, J., (1996) Tetrahedron Lett., 37, p. 5441Cooper, J., Gallagher, P.T., Knight, D.W., (1988) J. Chem. Soc., Chem. Commun., p. 509Knight, D.W., Lewis, N., Share, A.C., Haigh, D., (1993) Tetrahedron Asymm., 4, p. 625Kusano, G., Ogawa, H., Takahashi, A., Nozoe, S., Yokoyama, K., (1987) Chem. Pharm. Bull, 35, p. 3482Burgess, L.E., Gross, E.K.M., Jurka, J., (1996) Tetrahedron Lett., 37, p. 3255Larrow, J.F., Jacobsen, E.N., Gao, Y., Hong, Y., Nie, X., Zepp, C.M., (1994) J. Org. Chem., 59, p. 1939notenoteKolb, H.C., Vannieuwenhze, M.S., Sharpless, K.B., (1994) Chem. Rev., 94, p. 2483Thaning, M., Wistrand, L.-G., (1989) Acta Chemica Scandinavica, 43, p. 290Mulzer, J., Meier, A., (1996) J. Org. Chem., 61, p. 566Roemmele, R.C., Rapoport, H., (1989) J. Org. Chem., 54, p. 1866Greck, C., Ferreira, F., Genêt, J.P., (1996) Tetrahedron Lett., 37, p. 2031Agami, C., Couty, F., Mathieu, H., (1996) Tetrahedron Lett., 37, p. 4001notenot

  • Metal Carbene N-h Insertion Of Chiral α, α′-dialkyl α-diazoketones. A Novel And Concise Method For The Stereocontrolled Synthesis Of Fully Substituted Azetidines
    2015
    Co-Authors: Burtoloso A.c.b., Correia C.r.d.
    Abstract:

    The syntheses of all cis substituted azetidines were accomplished in few steps from L-serine in modest to high yields. The key step was based on a rhodium or copper carbenoid N-H insertion of α,α′- dialkyl-α-diazoketones to furnish cis-2,4-dialkyl-azetidin-3-ones as the only observable diastereoisomers. © 2004 Elsevier Ltd. All rights reserved.451733553358Kobayashi, J., Ishibashi, M., Walchli, M.R., Yamamura, S., Ohizumi, Y., (1996) J. Chem. Soc. Heterocycles, 42, p. 943Kobayashi, J., Cheng, J., Ishibashi, M., Walchli, M.R., Yamamura, S., Ohizumi, Y., (1991) J. Chem. Soc., Perkin Trans. 1, p. 1135Alvi, K.A., Jaspars, M., Crews, P., (1994) Bioorg. Biomed. Chem. Lett., 4, p. 2447Hiraki, T., Yamagiwa, Y., Kamikawa, T., (1995) Tetrahedron Lett., 36, p. 4841. , For previous synthesis of azetidine alkaloids and analogues, see:Takikawa, H., Maeda, T., Mori, K., (1995) Tetrahedron Lett., 36, p. 7689Yoda, H., Oguchi, T., Takabe, K., (1996) Tetrahedron: Asymmetry, 7, p. 2113Yashima, A., Takikawa, H., Mori, K., (1996) Liebigs Ann., 7, p. 1083Mori, K., (1996) J. Heterocyclic Chem., 33, p. 1497Yoda, H., Oguchi, T., Takabe, K., (1997) Tetrahedron Lett., 38, p. 3283Knapp, S., Dong, Y., (1997) Tetrahedron Lett., 38, p. 3813Takikawa, H., Maeda, T., Seki, M., (1997) J. Chem. Soc., Perkin Trans. 1, 2, p. 97Lin, G.Q., Liu, D.G., (1998) Heterocycles, 47, p. 337Lin, G.Q., Liu, D.G., (1999) Tetrahedron Lett., 40, p. 337Reference 2j cited in [3l]Salgado, A., Boeykens, M., Gauthier, C., Declercq, J., De Kimpe, N., (2002) Tetrahedron, 58, p. 2763Yoda, H., Uemura, T., Takabe, K., (2003) Tetrahedron Lett., 44, p. 977Salgado, A., Boeykens, M., Gauthier, C., Dejaegher, Y., Verniest, G., Lopin, C., Tehrani, K.A., De Kimpe, N., (2003) Tetrahedron, 59, p. 2231Dejaegher, Y., Kuz'Nenok, N.M., Zvonok, A.M., De Kimpe, N., (2002) Chem. Rev., 102, p. 29Doyle, M.P., McKervey, M.A., Ye, T., (1998) Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, , New York: John Wiley and SonsMoyer, M.P., Feldman, P.L., Rapoport, H., (1985) J. Org. Chem., 50, p. 5223Emmer, G., (1992) Tetrahedron, 48, p. 7165Hanessian, S., Fu, J., Chiara, J.L., Di Fabio, R., (1993) Tetrahedron Lett., 34, p. 4157Podlech, J., Seebach, D., (1995) Helv. Chim. Acta, 78, p. 1238Sengupta, S., Das, D., (1998) Synth. Commun., 28, p. 403Desai, P., Aubé, J., (2000) Org. Lett., 2, p. 1657Pusino, A., Saba, A., Desole, G., (1985) Gazzeta Chim. Italiana, 115, p. 33Wang, J., Hou, Y., Wu, P., (1999) J. Chem. Soc., Perkin Trans. 1, p. 2277Garner, P., Park, J.M., (1987) J. Org. Chem., 52, p. 2361notenoteCraig, D., Berry, M.B., (1992) Synlett, p. 41Taber, D.F., You, K.K., Rheigold, A.L., (1996) J. Am. Chem. Soc., 118, p. 547Doyle, M.P., Westrum, L.J., Wolthuis, W.N.E., See, M.M., Boone, W.P., Bagheri, V., Pearson, M.M., (1993) J. Am. Chem. Soc., 115, p. 958See reference 9 cited in reference 12 belowNakamura, E., Yoshikai, N., Yamanaka, M., (2002) J. Am. Chem. Soc., 124, p. 7181Davis, F.A., Yang, B., Deng, J., (2003) J. Org. Chem., 68, p. 5147not

  • Stereoselective Arylation Of Substituted Cyclopentenes By Substrate-directable Heck-matsuda Reactions: A Concise Total Synthesis Of The Sphingosine 1-phosphate Receptor (s1p1) Agonist Vpc01091
    2015
    Co-Authors: Oliveira C.c., Dos Santos E.a.f., Bormio Nunes J.h., Correia C.r.d.
    Abstract:

    We describe herein an efficient and diastereoselective substrate-directable Heck-Matsuda reaction with nonactivated five-membered olefins. The carbamate acts as the main directing group in the arylation process allowing the synthesis of several functionalized aryl cyclopentenes in good to excellent diastereoselectivities (>85:15) and in isolated yields ranging from 41 to 90%. No double bond isomerizations were observed in these Heck reactions, and the newly created benzylic centers were preserved in all cases examined. The substrate directable Heck arylation approach was successfully applied in a straightforward total synthesis of the sphingosine 1-phosphate receptor-subtype 1 (S1P1) agonist VPC01091 by a concise and practical route involving 5 steps in 40% overall yield. © 2012 American Chemical Society.771881828190Beletskaya, I.P., Cheprakov, A.V., (2000) Chem. 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  • Probing The Stereoselectivity Of The Heck Arylation Of Endocyclic Enecarbamates With Diazonium Salts. Concise Syntheses Of (2s,5r)-phenylproline Methyl Ester And Schramm's C-azanucleoside
    2015
    Co-Authors: Severino E.a., Costenaro E.r., Garcia A.l.l., Correia C.r.d.
    Abstract:

    (Matrix presented) The diastereoselectivity of the Heck arylation of several chiral, nonracemic, five.membered endocyclic enecarbamates with aryldiazonium tetrafluoroborates was evaluated. The cis selectivity observed for some enecarbamates bearing coordinating groups was explored in the concise synthesis of the (2S, SR)-(+)-phenylproline methyl ester, a scaffold for the nonpeptide cholecystokinin antagonist (+)-RP 66803, and in the synthesis of Schramm's potent antiprotozoan C-azanucleoside.53305308Whitcombe, N.J., Hii, M., Gibson, S.E., (2001) Tetrahedron, 57, p. 7449Beletskaya, I.P., Cheprakov, A.V., (2000) Chem. Rev., 100, p. 3009Shibasaki, M., Vogl, E.M., (1999) J. Organomet. Chem., 576, p. 1Crisp, G., (1998) Chem. Soc. Rev., 27, p. 427Shibasaki, M., Boden, D.J., Kojima, A., (1997) Tetrahedron, 53, p. 7371Andrus, M.B., Song, C., Zhang, J., (2002) Org. Lett., 4, p. 2079Brunner, H., Le Cousturier De Courcy, N., Genêt, J.-P., (1999) Tetrahedron Lett., 40, p. 4815Oliveira, D.F., Severino, E.A., Correia, C.R.D., (1999) Tetrahedron Lett., 40, p. 2083Mehta, G., Sengupta, S., (1996) Tetrahedron Lett., 37, p. 8625Beller, M., Kuhlein, K., (1995) Synlett, p. 441Iida, H., Yamazaki, N., Kibayashi, C., (1986) Tetrahedron Lett., 27, p. 5393Zaveri, N.T., (2001) Org. Lett., 3, p. 843Manfré, F., Pulicani, P., (1994) Tetrahedron: Asymmetry, 5, p. 235Miles, R.W., Tyler, P.C., Evans, G.B., Furneaux, R.H., Parkin, D.W., Schramm, V.L., (1999) Biochemistry, 38, p. 13147Severino, E.A., Correia, C.R.D., (2000) Org. Lett., 2, p. 3039Kikukawa, K., Nagira, K., Wada, F., Matsuda, T., (1981) Tetrahedron, 37, p. 31Lahoti, R.J., Parameswaran, V., Wagle, D.R., (1981) Ind. J. Chem., 20 B, p. 767Olofsson, K., Sahlin, H., Lathed, M., Hallberg, A., (2001) J. Org. Chem., 66, p. 544Nilsson, P., Larhed, M., Hallberg, A., (2001) J. Am. Chem. Soc., 123, p. 8217Olofsson, K., Larhed, M., Hallberg, A., (2000) J. Org. Chem., 65, p. 7235Itami, K., Mitsudo, K., Kamei, T., Koike, T., Nokami, T., Yoshida, J., (2000) J. Am. Chem. Soc., 122, p. 12013Buezo, N.D., Alonso, I., Carretero, J.C., (1998) J. Am. Chem. Soc., 120, p. 7129Kang, S.-K., Lee, H.-W., Jang, S.-B., K, T.-H., Pyun, S.-J., (1996) J. Org. Chem., 61, p. 2604Madin, A., Overman, L., (1992) Tetrahedron Lett., 33, p. 4859Haddad, M., Imogai, H., Larchevêque, M., (1998) J. Org. Chem., 63, p. 5680Davis, F.A., Fang, T., Goswami, R., (2002) Org. Lett., 4, p. 1599Momotake, A., Togo, H., Yokoyama, M., (1999) J. Chem. Soc., Perkin Trans. 1, p. 1193Betsbrugge, J.V., Nest, W.V.D., Verheyden, P., Tourwé, D., (1998) Tetrahedron, 54, p. 1753Zaluski, M.C.F., Coric, P., Thery, V., Gonzalez, W., Meudal, H., Turcaud, S., Michel, J.B., Roques, B.P., (1996) J. Med. Chem., 39, p. 2594noteMorel, C., (2000) Parasitol. Today, 16, p. 2Hammond, D.J., Gutteridge, W.E., (1984) Mol. Biochem. Parasitol., 13, p. 243Estupiñán, B., Schramm, V.L., (1994) J. Biol. Chem., 269, p. 23068Gopaul, D.N., Meyer, S., Degane, M., Sachettini, J.C., Schramm, V.L., (1996) Biochemistry, 35, p. 5963Parkin, D.W., Limberg, G., Tyler, P.C., Furneaux, R.H., Chen, X.-Y., Schramm, V.L., (1997) Biochemistry, 36, p. 3528Furneaux, R.H., Limberg, G., Tyler, P.C., Schramm, V.L., (1997) Tetrahedron, 53, p. 2915Miles, R.W., Tyler, P.C., Evans, G.B., Furneaux, R.H., Parkin, D.W., Schramm, V.L., (1999) Biochemistry, 38, p. 13147Degano, M., Almo, S., Sacchettini, J.C., Schramm, V.L., (1998) Biochemistry, 37, p. 6277not

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  • dna Tetrahedron nanostructures for biological applications biosensors and drug delivery
    Analyst, 2017
    Co-Authors: Nuli Xie, Xiaohai Yang, Jin Huang, Shiyuan Liu, Kemin Wang
    Abstract:

    With the rapid development of DNA nanotechnology, various DNA nanostructures with different shapes and sizes have been self-assembled using “bottom-up” fabrication strategies and applied to a wide range of fields such as biosensors, drug delivery and tools for molecular biology. As a classical and simple polyhedron, DNA Tetrahedron can be easily synthesised by a one-step assembly. Due to the excellent biocompatibility and cellular permeability, it provides a universal and promising platform to construct a series of biosensors and drug delivery systems for living cells studies. Moreover, the high programmability of DNA Tetrahedron determines its capability to perform artful design and combine with other materials. Herein, we review and summarise the development and applications of DNA Tetrahedron in living cell studies. We mainly focus on two parts, cellular biosensors for the detection of nucleic acids, proteins, small molecules and cancer cells and drug delivery systems for chemotherapy, immunotherapy, photodynamic therapy and gene silencing. With the rapid progress in DNA Tetrahedron as well as DNA nanotechnology, new avenues and opportunities have opened up in analytical chemistry, molecular biology and medicine.

  • a dna Tetrahedron based molecular beacon for tumor related mrna detection in living cells
    Chemical Communications, 2016
    Co-Authors: Nuli Xie, Xiaohai Yang, Jin Huang, Yanjing Yang, Ke Quan, He Wang, Le Ying, Kemin Wang
    Abstract:

    Due to its low cytotoxicity, high resistance to enzymatic degradation, and cellular permeability, a DNA Tetrahedron-based molecular beacon (DTMB) is designed for tumor-related TK1 mRNA detection in living cells, where the target sequence can induce the Tetrahedron from contraction to extension, resulting in fluorescence restoration.

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