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Pure Appl. Chem., 1985, Vol. 57, No. 3, pp. 441-451

http://dx.doi.org/10.1351/pac198557030441

Absolute configuration of in situ transition metal complexes of ligating natural products from circular dichroism

Jadwiga Frelek, Zsuzsa Majer, A. Perkowska, G. Snatzke, I. Vlahov and U. Wagner

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  • Schönemann Wojciech, Gallienne Estelle, Ikeda-Obatake Kyoko, Asano Naoki, Nakagawa Shinpei, Kato Atsushi, Adachi Isao, Górecki Marcin, Frelek Jadwiga, Martin Olivier R.: Glucosylceramide Mimics: Highly Potent GCase Inhibitors and Selective Pharmacological Chaperones for Mutations Associated with Types 1 and 2 Gaucher Disease. ChemMedChem 2013, 8, 1805. <http://dx.doi.org/10.1002/cmdc.201300327>
  • Majer Zsuzsa, Szilvágyi Gábor, Benedek László, Csámpai Antal, Hollósi Miklós, Vass Elemér: Chelate Structure of a Dirhodium-Amino Acid Complex Identified by Chiroptical and NMR Spectroscopy. Eur. J. Inorg. Chem. 2013, 2013, 3020. <http://dx.doi.org/10.1002/ejic.201300057>
  • Jawiczuk Magdalena, Górecki Marcin, Suszczyńska Agata, Karchier Michał, Jaźwiński Jarosław, Frelek Jadwiga: Dimolybdenum Tetracarboxylates as Auxiliary Chromophores in Chiroptical Studies of vic-Diols. Inorg. Chem. 2013, 52, 8250. <http://dx.doi.org/10.1021/ic401170m>
  • Frelek Jadwiga, Ruśkowska Patrycja, Suszczyńska Agata, Szewczyk Katarzyna, Osuch Anna, Jarosz Sławomir, Jagodziński Jacek: Configurational assignment of sugar erythro-1,2-diols from their electronic circular dichroism spectra with dimolybdenum tetraacetate. Tet Asymm 2008, 19, 1709. <http://dx.doi.org/10.1016/j.tetasy.2008.06.029>
  • Szilvágyi Gábor, Hollósi Miklós, Tölgyesi László, Frelek Jadwiga, Majer Zsuzsa: Dirhodium complexes of amino acid derivatives: separation and characterization by circular dichroism spectroscopy. Tet Asymm 2008, 19, 2594. <http://dx.doi.org/10.1016/j.tetasy.2008.11.013>
  • Frelek Jadwiga, Jaźwiński Jarosław, Masnyk Marek, Ruśkowska Patrycja, Szmigielski Rafał: Dirhodium tetraacetate as an auxiliary chromophore in a circular dichroic study on vic-amino alcohols. Tet Asymm 2005, 16, 2437. <http://dx.doi.org/10.1016/j.tetasy.2005.05.044>
  • Frelek Jadwiga, Górecki Marcin, Jaźwiński Jarosław, Masnyk Marek, Ruśkowska Patrycja, Szmigielski Rafał: Configurational assignment of vic-amino alcohols from their circular dichroism spectra with dirhodium tetracetate as an auxiliary chromophore. Tet Asymm 2005, 16, 3188. <http://dx.doi.org/10.1016/j.tetasy.2005.08.028>
  • Frelek Jadwiga, Klimek Agata, Ruśkowska Patrycja: Optical activity of vic-amino alcohols in the presence of dimolybdenum tetracetate. Tet Asymm 2002, 13, 2461. <http://dx.doi.org/10.1016/S0957-4166(02)00647-X>
  • Wang B, Ma H.Z: Chiroptical Lanthanide(III) schiff base complexes derived from p-Nitrophenyl-hydrazine and d-Camphor-β-sulphonic acid. J Inorg Chem Commun 2001, 4, 248. <http://dx.doi.org/10.1016/S1387-7003(01)00173-3>
  • Jarosz Slawomir, Mach Mateusz, Frelek Jadwiga: Synthesis and Structural Analysis of Higher Analogs of Sucrose. J Carbohydr Chem 2000, 19, 693. <http://dx.doi.org/10.1080/07328300008544111>
  • Frelek Jadwiga, Szczepek Wojciech, Voelter Wolfgang: Determination of the Absolute Configuration of Chiral 1,3-Diols by CD spectroscopy of their [Mo2(OAc)4] complexes. J Prakt Chem 1997, 339, 135. <http://dx.doi.org/10.1002/prac.19973390126>
  • Kuball Hans-Georg, Brüning Holger: Helical twisting power and circular dichroism as chirality observations: The intramolecular and intermolecular chirality transfer. Chirality 1997, 9, 407. <http://dx.doi.org/10.1002/(SICI)1520-636X(1997)9:5/6<407::AID-CHIR3>3.0.CO;2-2>
  • Frelek Jadwiga, Ikekawa Nobuo, Takatsuto Suguru, Snatzke (The Late) Günther: Application of [Mo2(OAc)4] for determination of absolute configuration of brassinosteroid vic-diols by circular dichroism. Chirality 1997, 9, 578. <http://dx.doi.org/10.1002/(SICI)1520-636X(1997)9:5/6<578::AID-CHIR27>3.0.CO;2-K>
  • Frelek Jadwiga, Pakulski Zbigniew, Zamojski Aleksander: Application of [Mo2(OAc)4] for determination of absolute configuration of pyranoid and furanoid vic-diols by circular dichroism. Tet Asymm 1996, 7, 1363. <http://dx.doi.org/10.1016/0957-4166(96)00153-X>
  • Cantín Oscar, Cativiela Carlos, Díaz-de-Villegas María D., Navarro Rafael, Urriolabeitia Esteban P.: A practical method for the absolute configuration assignment of α-amino acids using their Pd(dmba) amino acidato complexes. Tet Asymm 1996, 7, 2695. <http://dx.doi.org/10.1016/0957-4166(96)00346-1>
  • Gerards Michael: Circular dichroism of configurationally chiral dimolybdenum complexes with chiral diamine ligands. Inorg Chim Ada 1995, 229, 101. <http://dx.doi.org/10.1016/0020-1693(94)04233-L>
  • Ripperger Helmut, Nguyen Hoang Anh, Himmelreich Uwe, Tran Van Sung, Adam Günter: Polar eupomatenoids from Caryodaphnosis tonkinensis. Phytochemisry 1995, 39, 213. <http://dx.doi.org/10.1016/0031-9422(94)00890-6>
  • Jinxia Liu, Bo Wang, Wenjuan Xie, Shiyan Yang, Daosen Jin: Spectra and chiroptical studies on lanthanide(III) complexes of d-camphor-β-sulphonic acid. J Polyhedron 1994, 13, 2095. <http://dx.doi.org/10.1016/S0277-5387(00)83496-8>
  • Bick Stefan, Zimmermann Silke, Meuer Heike, Sheldrick William S., Welzel Peter: Synthesis of an advanced forskolin intermediate. Tetrahedron 1993, 49, 2457. <http://dx.doi.org/10.1016/S0040-4020(01)86324-9>
  • Frischmuth Katja, Wagner Ulrich, Samson Emmanuelle, Weigelt Dirk, Koll Peter, Meuer Heike, Sheldrick William S., Welzel Peter: Configurational assignment at C-2′ of some strigol analogues. Tet Asymm 1993, 4, 351. <http://dx.doi.org/10.1016/S0957-4166(00)86080-2>
  • Warnke Zygmunt, Wawrzyniak Grażyna, Chmurzynski Lech: INTERACTION BETWEEN TRINUCLEAR OXOCENTRED COORDINATION COMPOUNDS OF TRANSITION METALS AND ORGANIC SOLVENTS1. J Coord Chem 1993, 28, 271. <http://dx.doi.org/10.1080/00958979308037108>
  • Frelek Jadwiga, Pakulski Zbigniew, Zamojski Aleksander: Circular Dichroism of Transition Metal Complexes and Sugar Derivatives Having a Free 1,3-Diol System or “Isolated” Hydroxyl Group. J Carbohydr Chem 1993, 12, 625. <http://dx.doi.org/10.1080/07328309308019412>
  • Hedtmann Udo, Klintz Ralf, Hobert Kurt, Frelek Jadwiga, Vlahov Iontscho, Welzel Peter: A facile route to 20-hydroxyecdysone and side chain homologues from poststeron. Tetrahedron 1991, 47, 3753. <http://dx.doi.org/10.1016/S0040-4020(01)80901-7>
  • Beisswenger Roswitha, Snatzke Günther, Thiem Joachim, Kula Maria Regina: Enzyme-catalyzed aldol reactions with 3-hexulose phosphate synthase. Tetrahetron Lett 1991, 32, 3159. <http://dx.doi.org/10.1016/S0040-4039(00)79710-3>
  • Toome Voldemar, Wegrzynski Bogda: A Fast and Simple in Situ Method for the Determination of the Absolute Configuration of 2-and 3-Hydroxycarboxylic Acids, Esters and Ethers Using the Chiroptical Properties of Their Eu(Fod)3 Complexes. A Preliminary Report. Anal Lett 1991, 24, 317. <http://dx.doi.org/10.1080/00032719108052907>
  • Gerards Michael, Snatzke Günther: Circular dichroism, XCIII determination of the absolute configuration of alcohols, olefins, epoxides, and ethers from the CD of their “in situ” complexes with [Rh2(O2CCF3)4]. Tet Asymm 1990, 1, 221. <http://dx.doi.org/10.1016/S0957-4166(00)86328-4>
  • Hedtmann Udo, Hobert Kurt, Klintz Ralf, Welzel Peter, Frelek Jadwiga, Strangmann-Diekmann Magdalena, Klöne Antje, Pongs Olaf: Seitenkettenhomologe des 20-Hydroxyecdysons: Synthese, Konfigurationsbestimmung und biochemische Charakterisierung. Angew Chem 1989, 101, 1543. <http://dx.doi.org/10.1002/ange.19891011116>
  • Hedtmann Udo, Hobert Kurt, Klintz Ralf, Welzel Peter, Frelek Jadwiga, Strangmann-Diekmann Magdalena, Klöne Antje, Pongs Olaf: Side-chain Homologues of 20-Hydroxyecdysone: Synthesis, Configurational Assignment, and Biochemical Characterization. Angew Chem Int Ed Engl 1989, 28, 1515. <http://dx.doi.org/10.1002/anie.198915151>
  • Frelek Jadwiga, Majer-Decker Zsuzsa, Snatzke Günther: Determination of the absolute configuration of α-aminoalkylphosphonic acids from their CD in the presence of [Ru2(O2CC3H7)4]⊕ Cl⊖. Liebigs Ann Chem 1988, 1988, 281. <http://dx.doi.org/10.1002/jlac.198819880318>
  • Rodewald W. J., Piotrowski G. T.: Secosteroids. I. Synthesis of vic-Diols in B-Secocholestane Group. J prakt Chem 1988, 330, 775. <http://dx.doi.org/10.1002/prac.19883300513>
  • Signorella Sandra R., Cravero Raquel M., Sala Luis E., Rúveda Edmundo A.: Diastered and Regiochemical Control in the Functionalization of the Allylic [dbnd] of a Natural 5-(1-Alkenyl)-2-Enono-1,5-Lactone. Synth Common 1988, 18, 1935. <http://dx.doi.org/10.1080/00397918808068260>
  • Lipták András, Frelek Jadwiga, Snatzke Günther, Vlahov Iontscho: Chiroptical properties of pyranoid glycols in the presence of [Mo2(O[2CCH3)4]. Carbohydrates Research 1987, 164, 149. <http://dx.doi.org/10.1016/0008-6215(87)80127-1>
  • Roy Rita, Saha Manik C., Roy Parag S.: Coordination chemistry of f-block elements with imine acids. Part II. Studies on dioxouranium(VI) complexes of N-(salicylidene)-L-valine and N-(orthovanillidene)-L-valine. Inorg Chim Ada 1987, 129, 265. <http://dx.doi.org/10.1016/S0020-1693(00)86673-6>
  • Hedtmann Udo, Welzel Peter: A facile synthesis of the 20-hydroxyecdysone side chain via a dihydrofuran derivative. Tetrahetron Lett 1985, 26, 2773. <http://dx.doi.org/10.1016/S0040-4039(00)94908-6>