메뉴 건너뛰기




Volumn 40, Issue 7, 2014, Pages 687-699

Synthesis of 6-Substituted 1-oxoindanoyl Isoleucine Conjugates and Modeling Studies with the COI1-JAZ Co-Receptor Complex of Lima Bean

Author keywords

Chemical Probes; COI1 JAZ co receptor; Jasmonate; Lima bean (Phaseolus lunatus); Molecular modeling; Structure Activity Relationship; Volatile Organic Compounds (VOCs)

Indexed keywords

BIOACTIVITY; CARBOXYLIC ACID; FUNCTIONAL ROLE; HORMONE; INDUSTRIAL PRODUCTION; LEGUME; LIGAND; PROBE; REACTION KINETICS; VOLATILE ORGANIC COMPOUND;

EID: 84906076379     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-014-0469-2     Document Type: Article
Times cited : (16)

References (56)
  • 3
    • 0002062801 scopus 로고
    • Synthesis of organotrialkylstannanes. The reaction between organic halides and hexaalkyldistannanes in the presence of palladium complexes
    • Azizian H, Eaborn C, Pidcock A (1981) Synthesis of organotrialkylstannanes. The reaction between organic halides and hexaalkyldistannanes in the presence of palladium complexes. J Organomet Chem 215: 49-58.
    • (1981) J Organomet Chem , vol.215 , pp. 49-58
    • Azizian, H.1    Eaborn, C.2    Pidcock, A.3
  • 8
    • 0032809155 scopus 로고    scopus 로고
    • Jasmonic acid and herbivory differentially induce carnivore-attracting plant volatiles in lima bean plants
    • Dicke M, Gols R, Ludeking D, Posthumus MA (1999) Jasmonic acid and herbivory differentially induce carnivore-attracting plant volatiles in lima bean plants. J Chem Ecol 25: 1907-1922.
    • (1999) J Chem Ecol , vol.25 , pp. 1907-1922
    • Dicke, M.1    Gols, R.2    Ludeking, D.3    Posthumus, M.A.4
  • 10
    • 67749097780 scopus 로고    scopus 로고
    • Silver-mediated fluorination of functionalized aryl stannanes
    • Furuya T, Strom AE, Ritter T (2009) Silver-mediated fluorination of functionalized aryl stannanes. J Am Chem Soc 131: 1662-1663.
    • (2009) J Am Chem Soc , vol.131 , pp. 1662-1663
    • Furuya, T.1    Strom, A.E.2    Ritter, T.3
  • 11
    • 79957603696 scopus 로고    scopus 로고
    • Catalysis for fluorination and trifluoromethylation
    • Furuya T, Kamlet AS, Ritter T (2011) Catalysis for fluorination and trifluoromethylation. Nature 473: 470-477.
    • (2011) Nature , vol.473 , pp. 470-477
    • Furuya, T.1    Kamlet, A.S.2    Ritter, T.3
  • 12
    • 66349118842 scopus 로고    scopus 로고
    • Functionalized esters as bis-electrophiles in a silicon-induced domino synthesis of annulated carbocycles
    • Genrich F, Harms G, Schaumann E, Gjikaj M, Adiwidjaja G (2009) Functionalized esters as bis-electrophiles in a silicon-induced domino synthesis of annulated carbocycles. Tetrahedron 65: 5577-5587.
    • (2009) Tetrahedron , vol.65 , pp. 5577-5587
    • Genrich, F.1    Harms, G.2    Schaumann, E.3    Gjikaj, M.4    Adiwidjaja, G.5
  • 14
    • 5244268272 scopus 로고    scopus 로고
    • Merck molecular force field.5. Extension of MMFF94 using experimental data, additional computational data, and empirical rules
    • Halgren TA (1996) Merck molecular force field. 5. Extension of MMFF94 using experimental data, additional computational data, and empirical rules. J Comput Chem 17: 616-641.
    • (1996) J Comput Chem , vol.17 , pp. 616-641
    • Halgren, T.A.1
  • 18
    • 0000198223 scopus 로고
    • On the stereochemistry of coronatine: revised absolute configuration of (+)-coronamic acid
    • Ichihara A, Shiraishi K, Sakamura S (1979) On the stereochemistry of coronatine: revised absolute configuration of (+)-coronamic acid. Tetrahedron Lett 20: 365-368.
    • (1979) Tetrahedron Lett , vol.20 , pp. 365-368
    • Ichihara, A.1    Shiraishi, K.2    Sakamura, S.3
  • 19
    • 0035896350 scopus 로고    scopus 로고
    • Defensive function of herbivore-induced plant volatile emissions in nature
    • Kessler A, Baldwin IT (2001) Defensive function of herbivore-induced plant volatile emissions in nature. Science 291: 2141-2144.
    • (2001) Science , vol.291 , pp. 2141-2144
    • Kessler, A.1    Baldwin, I.T.2
  • 20
    • 0037132666 scopus 로고    scopus 로고
    • Copper-catalyzed halogen exchange in aryl halides: an aromatic finkelstein reaction
    • Klapars A, Buchwald SL (2002) Copper-catalyzed halogen exchange in aryl halides: an aromatic finkelstein reaction. J Am Chem Soc 124: 14844-14845.
    • (2002) J Am Chem Soc , vol.124 , pp. 14844-14845
    • Klapars, A.1    Buchwald, S.L.2
  • 21
    • 80055023023 scopus 로고    scopus 로고
    • Rational chemical design of the next generation of molecular imaging probes based on physics and biology: mixing modalities, colors and signals
    • Kobayashi H, Longmire MR, Ogawa M, Choyke PL (2011) Rational chemical design of the next generation of molecular imaging probes based on physics and biology: mixing modalities, colors and signals. Chem Soc Rev 40: 4626-4648.
    • (2011) Chem Soc Rev , vol.40 , pp. 4626-4648
    • Kobayashi, H.1    Longmire, M.R.2    Ogawa, M.3    Choyke, P.L.4
  • 22
    • 0000096835 scopus 로고    scopus 로고
    • Click chemistry: diverse chemical function from a few good reactions
    • Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 40: 2004-2021.
    • (2001) Angew Chem Int Ed , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 23
    • 70349138933 scopus 로고    scopus 로고
    • A rapid wound signal activates the systemic synthesis of bioactive jasmonates in Arabidopsis
    • Koo AJK, Gao X, Jones AD, Howe GA (2009) A rapid wound signal activates the systemic synthesis of bioactive jasmonates in Arabidopsis. Plant J 59: 974-986.
    • (2009) Plant J , vol.59 , pp. 974-986
    • Koo, A.J.K.1    Gao, X.2    Jones, A.D.3    Howe, G.A.4
  • 24
    • 44449130131 scopus 로고    scopus 로고
    • The defensive role of volatile emission and extrafloral nectar secretion for lima bean in nature
    • Kost C, Heil M (2008) The defensive role of volatile emission and extrafloral nectar secretion for lima bean in nature. J Chem Ecol 34: 2-13.
    • (2008) J Chem Ecol , vol.34 , pp. 2-13
    • Kost, C.1    Heil, M.2
  • 25
    • 0037093644 scopus 로고    scopus 로고
    • Increasing the precision of comparative models with YASARA NOVA - a self-parameterizing force field
    • Krieger E, Koraimann G, Vriend G (2002) Increasing the precision of comparative models with YASARA NOVA - a self-parameterizing force field. Proteins 47: 393-402.
    • (2002) Proteins , vol.47 , pp. 393-402
    • Krieger, E.1    Koraimann, G.2    Vriend, G.3
  • 26
    • 0035938287 scopus 로고    scopus 로고
    • Multiply bridgehead- and periphery-substituted tribenzotriquinacenes - highly versatile rigid molecular building blocks with C-3v or C-3 symmetry
    • Kuck D, Schuster A, Krause RA, Tellenbröker J, Exner CP, Penk M, Bögge H, Müller A (2001) Multiply bridgehead- and periphery-substituted tribenzotriquinacenes - highly versatile rigid molecular building blocks with C-3v or C-3 symmetry. Tetrahedron 57: 3587-3613.
    • (2001) Tetrahedron , vol.57 , pp. 3587-3613
    • Kuck, D.1    Schuster, A.2    Krause, R.A.3    Tellenbröker, J.4    Exner, C.P.5    Penk, M.6    Bögge, H.7    Müller, A.8
  • 27
    • 0038161270 scopus 로고    scopus 로고
    • Indanoyl amino acid conjugates: tunable elicitors of plant secondary metabolism
    • Lauchli R, Boland W (2003) Indanoyl amino acid conjugates: tunable elicitors of plant secondary metabolism. Chem Rec 3: 12-21.
    • (2003) Chem Rec , vol.3 , pp. 12-21
    • Lauchli, R.1    Boland, W.2
  • 28
    • 0036898054 scopus 로고    scopus 로고
    • Selective induction of secondary metabolism in Phaseolus lunatus by 6-substituted indanoyl isoleucine conjugates
    • Lauchli R, Schüler G, Boland W (2002) Selective induction of secondary metabolism in Phaseolus lunatus by 6-substituted indanoyl isoleucine conjugates. Phytochemistry 61: 807-817.
    • (2002) Phytochemistry , vol.61 , pp. 807-817
    • Lauchli, R.1    Schüler, G.2    Boland, W.3
  • 29
    • 20444481934 scopus 로고    scopus 로고
    • Structural and biological diversity of cyclic octadecanoids, jasmonates, and mimetics
    • Mithöfer A, Maitrejean M, Boland W (2005) Structural and biological diversity of cyclic octadecanoids, jasmonates, and mimetics. J Plant Growth Regul 23: 170-178.
    • (2005) J Plant Growth Regul , vol.23 , pp. 170-178
    • Mithöfer, A.1    Maitrejean, M.2    Boland, W.3
  • 30
    • 68949195873 scopus 로고    scopus 로고
    • Total syntheses of coronatines by exo-selective Diels-Alder reaction and their biological activities on stomatal opening
    • Okada M, Ito S, Matsubara A, Iwakura I, Egoshi S, Ueda M (2009) Total syntheses of coronatines by exo-selective Diels-Alder reaction and their biological activities on stomatal opening. Org Bio Chem 7: 3065-3073.
    • (2009) Org Bio Chem , vol.7 , pp. 3065-3073
    • Okada, M.1    Ito, S.2    Matsubara, A.3    Iwakura, I.4    Egoshi, S.5    Ueda, M.6
  • 31
    • 78049391969 scopus 로고    scopus 로고
    • Azido-coronatine: a useful platform for "click chemistry"-mediated probe synthesis for bioorganic studies
    • Okada M, Egoshi S, Ueda M (2010) Azido-coronatine: a useful platform for "click chemistry"-mediated probe synthesis for bioorganic studies. Biosci Biotechnol Biochem 74: 2092-2095.
    • (2010) Biosci Biotechnol Biochem , vol.74 , pp. 2092-2095
    • Okada, M.1    Egoshi, S.2    Ueda, M.3
  • 32
    • 40049102468 scopus 로고    scopus 로고
    • Jasmonates and its mimics differentially elicit systemic defence responses in Nicotiana attenuata
    • Pluskota WE, Qu N, Maitrejean M, Boland W, Baldwin IT (2007) Jasmonates and its mimics differentially elicit systemic defence responses in Nicotiana attenuata. J Exp Bot 58: 4071-4082.
    • (2007) J Exp Bot , vol.58 , pp. 4071-4082
    • Pluskota, W.E.1    Qu, N.2    Maitrejean, M.3    Boland, W.4    Baldwin, I.T.5
  • 33
    • 33644914780 scopus 로고    scopus 로고
    • Synthesis of conjugated 2,7-bis (trimethylsilylethynyl)-(phenylethynyl) nfluoren-9-one and 9-(p-methoxyphenyl)-9-methyl derivatives: optical properties
    • Rodriguez JG, Tejedor JL, Parra TL, Diaz C (2006) Synthesis of conjugated 2, 7-bis (trimethylsilylethynyl)-(phenylethynyl) nfluoren-9-one and 9-(p-methoxyphenyl)-9-methyl derivatives: optical properties. Tetrahedron 62: 3355-3361.
    • (2006) Tetrahedron , vol.62 , pp. 3355-3361
    • Rodriguez, J.G.1    Tejedor, J.L.2    Parra, T.L.3    Diaz, C.4
  • 34
    • 47749092147 scopus 로고    scopus 로고
    • Horticultural applications of jasmonates: A review
    • Rohwer CL, Erwin JE (2008) Horticultural applications of jasmonates: A review. J Hortic Sci Biotechnol 83: 283-304.
    • (2008) J Hortic Sci Biotechnol , vol.83 , pp. 283-304
    • Rohwer, C.L.1    Erwin, J.E.2
  • 36
    • 0033605828 scopus 로고    scopus 로고
    • Synthesis of 6-azido-1-oxo-indan-4-oyl isoleucine; a photoaffinity approach to plant signaling
    • Schüler G, Wasternack C, Boland W (1999) Synthesis of 6-azido-1-oxo-indan-4-oyl isoleucine; a photoaffinity approach to plant signaling. Tetrahedron 55: 3897-3904.
    • (1999) Tetrahedron , vol.55 , pp. 3897-3904
    • Schüler, G.1    Wasternack, C.2    Boland, W.3
  • 37
    • 0035034389 scopus 로고    scopus 로고
    • 6-Substituted indanoyl isoleucine conjugates mimic the biological activity of coronatine
    • Schüler G, Görls H, Boland W (2001) 6-Substituted indanoyl isoleucine conjugates mimic the biological activity of coronatine. Eur J Org Chem 1663-1668.
    • (2001) Eur J Org Chem , pp. 1663-1668
    • Schüler, G.1    Görls, H.2    Boland, W.3
  • 40
    • 62249196848 scopus 로고    scopus 로고
    • Metal-catalysed halogen exchange reactions of aryl halides
    • Sheppard TD (2009) Metal-catalysed halogen exchange reactions of aryl halides. Org Biomol Chem 7: 1043-1052.
    • (2009) Org Biomol Chem , vol.7 , pp. 1043-1052
    • Sheppard, T.D.1
  • 41
    • 10044258626 scopus 로고    scopus 로고
    • A fluorogenic 1,3-dipolar cycloaddition reaction of 3-azidocoumarins and acetylenes
    • Sivakumar K, Xie F, Cash BM, Long S, Barnhill HN, Wang Q (2004) A fluorogenic 1, 3-dipolar cycloaddition reaction of 3-azidocoumarins and acetylenes. Org Lett 6: 4603-4606.
    • (2004) Org Lett , vol.6 , pp. 4603-4606
    • Sivakumar, K.1    Xie, F.2    Cash, B.M.3    Long, S.4    Barnhill, H.N.5    Wang, Q.6
  • 42
    • 70349917806 scopus 로고    scopus 로고
    • Bioorthogonal chemistry: fishing for selectivity in a sea of functionality
    • Sletten EM, Bertozzi CR (2009) Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed 48: 6974-6998.
    • (2009) Angew Chem Int Ed , vol.48 , pp. 6974-6998
    • Sletten, E.M.1    Bertozzi, C.R.2
  • 43
    • 34250361145 scopus 로고    scopus 로고
    • Dehydrogenation of ocimene by active carbon: artefact formation during headspace sampling from leaves of Phaseolus lunatus
    • Sonwa MM, Kost C, Biedermann A, Wegener R, Schulz S, Boland W (2007) Dehydrogenation of ocimene by active carbon: artefact formation during headspace sampling from leaves of Phaseolus lunatus. ARKIVOC 3: 164-172.
    • (2007) Arkivoc , vol.3 , pp. 164-172
    • Sonwa, M.M.1    Kost, C.2    Biedermann, A.3    Wegener, R.4    Schulz, S.5    Boland, W.6
  • 45
    • 11244341141 scopus 로고    scopus 로고
    • Dihydrocoronatine, promising candidate for a chemical probe to study coronatine-, jasmonoid- and octadecanoid-binding protein
    • Suzuki M, Hasegawa M, Kodama O, Toshima H (2004) Dihydrocoronatine, promising candidate for a chemical probe to study coronatine-, jasmonoid- and octadecanoid-binding protein. Biosci Biotechnol Biochem 68: 1617-1620.
    • (2004) Biosci Biotechnol Biochem , vol.68 , pp. 1617-1620
    • Suzuki, M.1    Hasegawa, M.2    Kodama, O.3    Toshima, H.4
  • 46
    • 77955431523 scopus 로고    scopus 로고
    • Plant defense elicitors: analogues of jasmonoyl-isoleucine conjugate
    • Svoboda J, Boland W (2010) Plant defense elicitors: analogues of jasmonoyl-isoleucine conjugate. Phytochemistry 71: 1445-1449.
    • (2010) Phytochemistry , vol.71 , pp. 1445-1449
    • Svoboda, J.1    Boland, W.2
  • 47
    • 64149107538 scopus 로고    scopus 로고
    • Synthesis of (+)-coronafacic acid
    • Taber DF, Sheth RB, Tian WJ (2009) Synthesis of (+)-coronafacic acid. J Org Chem 74: 2433-2437.
    • (2009) J Org Chem , vol.74 , pp. 2433-2437
    • Taber, D.F.1    Sheth, R.B.2    Tian, W.J.3
  • 48
    • 77956085609 scopus 로고    scopus 로고
    • Silver-catalyzed late-stage fluorination
    • Tang P, Furuya T, Ritter T (2010) Silver-catalyzed late-stage fluorination. J Am Chem Soc 132: 12150-12154.
    • (2010) J Am Chem Soc , vol.132 , pp. 12150-12154
    • Tang, P.1    Furuya, T.2    Ritter, T.3
  • 53
    • 67650717993 scopus 로고    scopus 로고
    • A general and efficient Suzuki-Miyaura cross-coupling protocol using weak base and no water: the essential role of acetate
    • Wang B, Sun H-X, Sun Z-H (2009) A general and efficient Suzuki-Miyaura cross-coupling protocol using weak base and no water: the essential role of acetate. Eur J Org Chem 3688-3692.
    • (2009) Eur J Org Chem , pp. 3688-3692
    • Wang, B.1    Sun, H.-X.2    Sun, Z.-H.3
  • 54
    • 84895067416 scopus 로고    scopus 로고
    • Action of jasmonates in plant stress responses and development-Applied aspects
    • Wasternack C (2014) Action of jasmonates in plant stress responses and development-Applied aspects. Biotechnol Adv 32: 31-39.
    • (2014) Biotechnol Adv , vol.32 , pp. 31-39
    • Wasternack, C.1
  • 55
    • 84878308492 scopus 로고    scopus 로고
    • Jasmonate: biosynthesis, perception, signal transduction and action in plant stress response, growth and development. An update to the 2007 review in Annals of Botany
    • Wasternack C, Hause B (2013) Jasmonate: biosynthesis, perception, signal transduction and action in plant stress response, growth and development. An update to the 2007 review in Annals of Botany. Ann Bot 111: 1021-1058.
    • (2013) Ann Bot , vol.111 , pp. 1021-1058
    • Wasternack, C.1    Hause, B.2
  • 56
    • 10044243843 scopus 로고    scopus 로고
    • Generalized born model: Analysis, refinement, and applications to proteins
    • Wojciechowski M, Leysyng B (2004) Generalized born model: Analysis, refinement, and applications to proteins. J Phys Chem B 108: 18368-18376.
    • (2004) J Phys Chem B , vol.108 , pp. 18368-18376
    • Wojciechowski, M.1    Leysyng, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.