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Since the beginning of the nuclear industry, graphite has been widely used as a moderator and reflector of neutrons in nuclear power reactors. Some reactors are relatively old and have already been shut down. As a result, a large amount of irradiated graphite has been generated. Although several thousand papers in the International Nuclear Information Service (INIS) database have discussed the management of radioactive waste containing graphite, knowledge of this problem is not common. The aim of the paper is to present the current status of the methods used in different countries to manage graphite-containing radioactive waste. Attention has been paid to the methods of handling spent TRISO fuel after its discharge from high-temperature gas-cooled reactors (HTGR) reactors.
Leon Fuks; Irena Herdzik-Koniecko; Katarzyna Kiegiel; Grazyna Zakrzewska-Koltuniewicz. Management of Radioactive Waste Containing Graphite: Overview of Methods. Energies 2020, 13, 4638 .
AMA StyleLeon Fuks, Irena Herdzik-Koniecko, Katarzyna Kiegiel, Grazyna Zakrzewska-Koltuniewicz. Management of Radioactive Waste Containing Graphite: Overview of Methods. Energies. 2020; 13 (18):4638.
Chicago/Turabian StyleLeon Fuks; Irena Herdzik-Koniecko; Katarzyna Kiegiel; Grazyna Zakrzewska-Koltuniewicz. 2020. "Management of Radioactive Waste Containing Graphite: Overview of Methods." Energies 13, no. 18: 4638.
Katarzyna Kiegiel; Dorota Gajda; Grażyna Zakrzewska-Kołtuniewicz. Recovery of uranium and other valuable metals from substrates and waste from copper and phosphate industries. Separation Science and Technology 2019, 55, 2099 -2107.
AMA StyleKatarzyna Kiegiel, Dorota Gajda, Grażyna Zakrzewska-Kołtuniewicz. Recovery of uranium and other valuable metals from substrates and waste from copper and phosphate industries. Separation Science and Technology. 2019; 55 (12):2099-2107.
Chicago/Turabian StyleKatarzyna Kiegiel; Dorota Gajda; Grażyna Zakrzewska-Kołtuniewicz. 2019. "Recovery of uranium and other valuable metals from substrates and waste from copper and phosphate industries." Separation Science and Technology 55, no. 12: 2099-2107.
Most European countries import phosphate rocks for mineral phosphate fertilizer production. In 2017, approximately 5.5 million t phosphate rocks were imported into the EU-28 and subsequently processed. Phosphate rock can contain relevant amounts of accompanying uranium as well as rare earth elements that can be recovered during phosphate fertilizer production. Recovering uranium from phosphate rock is a proven process that has been used on an industrial scale in North America, Europe, and Asia in the 1980s until decreasing uranium prices in the 1990s made this practice uneconomic. In this work, we estimate the amount of uranium contained in EU phosphate rock imports in 2017 using publicly available data from Eurostat as well as average uranium concentrations found in the exporting countries and discuss potential recoverable quantities. Results of this estimate indicate that a maximum of 334 t natural uranium could have theoretically been recovered from 2017 EU phosphate rock imports. This amount of uranium could have supported approximately 2.1% of the EU nuclear power fleets 2016 natural uranium requirements and is of the same order of magnitude as domestic EU uranium production.
Harikrishnan Tulsidas; Sophie Gabriel; Katarzyna Kiegiel; Nils Haneklaus. Uranium resources in EU phosphate rock imports. Resources Policy 2019, 61, 151 -156.
AMA StyleHarikrishnan Tulsidas, Sophie Gabriel, Katarzyna Kiegiel, Nils Haneklaus. Uranium resources in EU phosphate rock imports. Resources Policy. 2019; 61 ():151-156.
Chicago/Turabian StyleHarikrishnan Tulsidas; Sophie Gabriel; Katarzyna Kiegiel; Nils Haneklaus. 2019. "Uranium resources in EU phosphate rock imports." Resources Policy 61, no. : 151-156.
Along with the increasing development of electric and electronic industries, the demand for rare earth elements is also growing due to their high position in many applications. In Poland, there are minerals containing REE; however, the concentration of these elements in raw materials is rather low, so they do not have a big impact on the national economy. The potential source of REE is secondary materials; among them are phosphogypsum, uranium tailings, and the waste electrical and electronic equipment (WEEE). Lanthanides as accompanying metals of uranium in Polish uranium ores were leached in the technology of uranium recovery from these resources. The recovery of REE from pregnant liquors was conducted by solvent extraction and ion exchange. Novel apparatus solutions like membrane contactors in extraction stage were tested. Different types of matrices (uranium ore, phosphorites, etc.) were used.
Katarzyna Kiegiel; Agnieszka Miśkiewicz; Irena Herdzik-Koniecko; Dorota Gajda; Grażyna Zakrzewska-Kołtuniewicz. Perspective of Obtaining Rare Earth Elements in Poland. Lanthanides 2019, 1 .
AMA StyleKatarzyna Kiegiel, Agnieszka Miśkiewicz, Irena Herdzik-Koniecko, Dorota Gajda, Grażyna Zakrzewska-Kołtuniewicz. Perspective of Obtaining Rare Earth Elements in Poland. Lanthanides. 2019; ():1.
Chicago/Turabian StyleKatarzyna Kiegiel; Agnieszka Miśkiewicz; Irena Herdzik-Koniecko; Dorota Gajda; Grażyna Zakrzewska-Kołtuniewicz. 2019. "Perspective of Obtaining Rare Earth Elements in Poland." Lanthanides , no. : 1.
Katarzyna Kiegiel; Agnieszka Miśkiewicz; Dorota Gajda; Sylwester Sommer; Stanislaw Wolkowicz; Grażyna Zakrzewska-Koltuniewicz. Uranium in Poland: Resources and Recovery from Low-Grade Ores. Uranium - Safety, Resources, Separation and Thermodynamic Calculation 2018, 1 .
AMA StyleKatarzyna Kiegiel, Agnieszka Miśkiewicz, Dorota Gajda, Sylwester Sommer, Stanislaw Wolkowicz, Grażyna Zakrzewska-Koltuniewicz. Uranium in Poland: Resources and Recovery from Low-Grade Ores. Uranium - Safety, Resources, Separation and Thermodynamic Calculation. 2018; ():1.
Chicago/Turabian StyleKatarzyna Kiegiel; Agnieszka Miśkiewicz; Dorota Gajda; Sylwester Sommer; Stanislaw Wolkowicz; Grażyna Zakrzewska-Koltuniewicz. 2018. "Uranium in Poland: Resources and Recovery from Low-Grade Ores." Uranium - Safety, Resources, Separation and Thermodynamic Calculation , no. : 1.
A number of primary ores such as phosphate rock, gold-, copper- and rare earth ores contain considerable amounts of accompanying uranium and other critical materials. Energy neutral mineral processing is the extraction of unconventional uranium during primary ore processing to use it, after enrichment and fuel production, to generate greenhouse gas lean energy in a nuclear reactor. Energy neutrality is reached if the energy produced from the extracted uranium is equal to or larger than the energy required for primary ore processing, uranium extraction, -conversion, -enrichment and -fuel production. This work discusses the sustainability of energy neutral mineral processing and provides an overview of the current progress of a multinational research project on that topic conducted under the umbrella of the International Atomic Energy Agency.
Frederik Reitsma; Peter Woods; Martin Fairclough; Yongjin Kim; Harikrishnan Tulsidas; Luis Lopez; Yanhua Zheng; Ahmed Hussein; Gerd Brinkmann; Nils Haneklaus; Anand Kacham; Tumuluri Sreenivas; Agus Sumaryanto; Kurnia Trinopiawan; Nahhar Al Khaledi; Ahmad Zahari; Adil El Yahyaoui; Jamil Ahmad; Rolando Reyes; Katarzyna Kiegiel; Noureddine Abbes; Dennis Mwalongo; Eduardo Greaves. On the Sustainability and Progress of Energy Neutral Mineral Processing. Sustainability 2018, 10, 235 .
AMA StyleFrederik Reitsma, Peter Woods, Martin Fairclough, Yongjin Kim, Harikrishnan Tulsidas, Luis Lopez, Yanhua Zheng, Ahmed Hussein, Gerd Brinkmann, Nils Haneklaus, Anand Kacham, Tumuluri Sreenivas, Agus Sumaryanto, Kurnia Trinopiawan, Nahhar Al Khaledi, Ahmad Zahari, Adil El Yahyaoui, Jamil Ahmad, Rolando Reyes, Katarzyna Kiegiel, Noureddine Abbes, Dennis Mwalongo, Eduardo Greaves. On the Sustainability and Progress of Energy Neutral Mineral Processing. Sustainability. 2018; 10 (1):235.
Chicago/Turabian StyleFrederik Reitsma; Peter Woods; Martin Fairclough; Yongjin Kim; Harikrishnan Tulsidas; Luis Lopez; Yanhua Zheng; Ahmed Hussein; Gerd Brinkmann; Nils Haneklaus; Anand Kacham; Tumuluri Sreenivas; Agus Sumaryanto; Kurnia Trinopiawan; Nahhar Al Khaledi; Ahmad Zahari; Adil El Yahyaoui; Jamil Ahmad; Rolando Reyes; Katarzyna Kiegiel; Noureddine Abbes; Dennis Mwalongo; Eduardo Greaves. 2018. "On the Sustainability and Progress of Energy Neutral Mineral Processing." Sustainability 10, no. 1: 235.
Anna Abramowska; Dorota K. Gajda; Katarzyna Kiegiel; Agnieszka Miśkiewicz; Przemysław Drzewicz; Grażyna Zakrzewska-Kołtuniewicz. Purification of flowback fluids after hydraulic fracturing of Polish gas shales by hybrid methods. Separation Science and Technology 2017, 53, 1207 -1217.
AMA StyleAnna Abramowska, Dorota K. Gajda, Katarzyna Kiegiel, Agnieszka Miśkiewicz, Przemysław Drzewicz, Grażyna Zakrzewska-Kołtuniewicz. Purification of flowback fluids after hydraulic fracturing of Polish gas shales by hybrid methods. Separation Science and Technology. 2017; 53 (8):1207-1217.
Chicago/Turabian StyleAnna Abramowska; Dorota K. Gajda; Katarzyna Kiegiel; Agnieszka Miśkiewicz; Przemysław Drzewicz; Grażyna Zakrzewska-Kołtuniewicz. 2017. "Purification of flowback fluids after hydraulic fracturing of Polish gas shales by hybrid methods." Separation Science and Technology 53, no. 8: 1207-1217.
Solvent extraction of uranium from acidic and alkaline post-leaching liquors that were obtained by leaching of Polish ores is reported in this paper. The stripping of uranium from organic to aqueous phase was also studied. The synergistic mixture of 2-diethylhexylphosphoric acid (D2EHPA) and tri-n-butylphosphate (0.2 M:0.2 M) was found as a good extracting agent for uranium. Recovery of uranium was reached even 98 %. The effect of such parameters like uranium concentration and concentration of reagents used in the experiments was evaluated in advance by using a model uranium solutions.
Katarzyna Kiegiel; Anna Abramowska; Paweł Biełuszka; Grażyna Zakrzewska-Kołtuniewicz; Stanisław Wołkowicz. Solvent extraction of uranium from leach solutions obtained in processing of Polish low-grade ores. Journal of Radioanalytical and Nuclear Chemistry 2016, 311, 589 -598.
AMA StyleKatarzyna Kiegiel, Anna Abramowska, Paweł Biełuszka, Grażyna Zakrzewska-Kołtuniewicz, Stanisław Wołkowicz. Solvent extraction of uranium from leach solutions obtained in processing of Polish low-grade ores. Journal of Radioanalytical and Nuclear Chemistry. 2016; 311 (1):589-598.
Chicago/Turabian StyleKatarzyna Kiegiel; Anna Abramowska; Paweł Biełuszka; Grażyna Zakrzewska-Kołtuniewicz; Stanisław Wołkowicz. 2016. "Solvent extraction of uranium from leach solutions obtained in processing of Polish low-grade ores." Journal of Radioanalytical and Nuclear Chemistry 311, no. 1: 589-598.
The main objective of the present study was an assessment of the possibility of uranium recovery from domestic resources in Poland. In the first stage uranium was leached from the ground uranium ore by using acidic (sulfuric acid or hydrochloric acid) or alkaline (carbonate) solutions. The leaching efficiencies of uranium were dependent on the type of ore and it reached 81% for Dictyonemic shales and almost 100% for sandstones. The novel leaching routes, with the application of the helical membrane contactor equipped with rotating part were tested. The obtained postleaching solutions were concentrated and purified using solvent extraction or ion exchange chromatography. New methods of solvent extraction, as well as hybrid processes for separation and purification of the product, were studied. Extraction with the use of membrane capillary contactors that has many advantages above conventional methods was also proposed as an alternative purification method. The final product U3O8 could be obtained by the precipitation of ‘yellow cake’, followed by calcination step. The results of precipitation of ammonium diuranate and uranium peroxide from diluted uranium solution were presented
Katarzyna Kiegiel; Grażyna Zakrzewska-Kołtuniewicz; Dorota Gajda; Agnieszka Miśkiewicz; Anna Abramowska; Paweł Biełuszka; Bożena Danko; Ewelina Chajduk; Stanisław Wołkowicz. Dictyonema black shale and Triassic sandstones as potential sources of uranium. Nukleonika 2015, 60, 515 -522.
AMA StyleKatarzyna Kiegiel, Grażyna Zakrzewska-Kołtuniewicz, Dorota Gajda, Agnieszka Miśkiewicz, Anna Abramowska, Paweł Biełuszka, Bożena Danko, Ewelina Chajduk, Stanisław Wołkowicz. Dictyonema black shale and Triassic sandstones as potential sources of uranium. Nukleonika. 2015; 60 (3):515-522.
Chicago/Turabian StyleKatarzyna Kiegiel; Grażyna Zakrzewska-Kołtuniewicz; Dorota Gajda; Agnieszka Miśkiewicz; Anna Abramowska; Paweł Biełuszka; Bożena Danko; Ewelina Chajduk; Stanisław Wołkowicz. 2015. "Dictyonema black shale and Triassic sandstones as potential sources of uranium." Nukleonika 60, no. 3: 515-522.
The recovery of uranium and other valuable metals from Polish Peribaltic sandstones were examined. The solid–liquid extraction is the first stage of the technology of uranium production and it is crucial for the next stages of processing. In the laboratory experiments uranium was leached with efficiencies 71–100 % by acidic lixiviants. Satisfactory results were obtained for the alkaline leaching process. Almost 100 % of uranium was leached with alkaline carbonate solution. In post leaching solutions only uranium and small amounts of vanadium were present.
Dorota Gajda; Katarzyna Kiegiel; Grazyna Zakrzewska-Koltuniewicz; Ewelina Chajduk; Iwona Bartosiewicz; Stanisław Wołkowicz. Mineralogy and uranium leaching of ores from Triassic Peribaltic sandstones. Journal of Radioanalytical and Nuclear Chemistry 2014, 303, 521 -529.
AMA StyleDorota Gajda, Katarzyna Kiegiel, Grazyna Zakrzewska-Koltuniewicz, Ewelina Chajduk, Iwona Bartosiewicz, Stanisław Wołkowicz. Mineralogy and uranium leaching of ores from Triassic Peribaltic sandstones. Journal of Radioanalytical and Nuclear Chemistry. 2014; 303 (1):521-529.
Chicago/Turabian StyleDorota Gajda; Katarzyna Kiegiel; Grazyna Zakrzewska-Koltuniewicz; Ewelina Chajduk; Iwona Bartosiewicz; Stanisław Wołkowicz. 2014. "Mineralogy and uranium leaching of ores from Triassic Peribaltic sandstones." Journal of Radioanalytical and Nuclear Chemistry 303, no. 1: 521-529.
The crystal structure of the title compound, C5H4N2O2, is built of acid molecules located on a mirror plane. They form sheets stacked along the b-axis direction. The molecules interact via O—H...N hydrogen bonds, forming [001] chains, and weak van der Waals interactions
Katarzyna Kiegiel; Wojciech Starosta; Janusz Leciejewicz. Pyrimidine-4-carboxylic acid. Acta Crystallographica Section E Structure Reports Online 2013, 69, o885 -o885.
AMA StyleKatarzyna Kiegiel, Wojciech Starosta, Janusz Leciejewicz. Pyrimidine-4-carboxylic acid. Acta Crystallographica Section E Structure Reports Online. 2013; 69 (6):o885-o885.
Chicago/Turabian StyleKatarzyna Kiegiel; Wojciech Starosta; Janusz Leciejewicz. 2013. "Pyrimidine-4-carboxylic acid." Acta Crystallographica Section E Structure Reports Online 69, no. 6: o885-o885.
In the title compound, [Mg(C6H2N2O4)(H2O)4]·H2O, the MgII ion is coordinated by a fully deprotonated pyrimidine-4,6-dicarboxylate molecule, via a ring N and a carboxylate O atom, and by four water O atoms at the apices of a slightly distorted octahedron. In the crystal, molecules are linked by O—H...O and O—H...N hydrogen bonds, forming a three-dimensional network
Wojciech Starosta; Janusz Leciejewicz; Katarzyna Kiegiel. Tetraaqua(pyrimidine-4,6-dicarboxylato-κ2N1,O6)magnesium monohydrate. Acta Crystallographica Section E Structure Reports Online 2013, 69, m189 -m189.
AMA StyleWojciech Starosta, Janusz Leciejewicz, Katarzyna Kiegiel. Tetraaqua(pyrimidine-4,6-dicarboxylato-κ2N1,O6)magnesium monohydrate. Acta Crystallographica Section E Structure Reports Online. 2013; 69 (4):m189-m189.
Chicago/Turabian StyleWojciech Starosta; Janusz Leciejewicz; Katarzyna Kiegiel. 2013. "Tetraaqua(pyrimidine-4,6-dicarboxylato-κ2N1,O6)magnesium monohydrate." Acta Crystallographica Section E Structure Reports Online 69, no. 4: m189-m189.
Calixarenes represent a well-known family of macrocyclic molecules with broad range of potential applications in chemical, analytical, and engineering materials fields. This paper covers the use of calixarenes as complexing agents for uranium(VI). The high effectiveness of calix[6]arenes in comparison to other calixarenes in uranium(VI) separation process is also presented. Processes such as liquid-liquid extraction (LLE), liquid membrane (LM) separation, and ion exchange are considered as potential fields for application of calixarenes as useful agents for bindingUO22+for effective separation from aqueous solutions containing other metal components.
Katarzyna Kiegiel; Lukasz Steczek; Grazyna Zakrzewska-Trznadel. Application of Calixarenes as Macrocyclic Ligands for Uranium(VI): A Review. Journal of Chemistry 2013, 2013, 1 -16.
AMA StyleKatarzyna Kiegiel, Lukasz Steczek, Grazyna Zakrzewska-Trznadel. Application of Calixarenes as Macrocyclic Ligands for Uranium(VI): A Review. Journal of Chemistry. 2013; 2013 (37):1-16.
Chicago/Turabian StyleKatarzyna Kiegiel; Lukasz Steczek; Grazyna Zakrzewska-Trznadel. 2013. "Application of Calixarenes as Macrocyclic Ligands for Uranium(VI): A Review." Journal of Chemistry 2013, no. 37: 1-16.
K. Raszplewicz; L. Sikorska; Katarzyna Kiegiel; T. Balakier; Janusz Jurczak. Diastereoselective Addition of Grignard Reagents to Chiral α-Ketoimides Derived from Oppolzer′s Sultam. ChemInform 2006, 37, 1 .
AMA StyleK. Raszplewicz, L. Sikorska, Katarzyna Kiegiel, T. Balakier, Janusz Jurczak. Diastereoselective Addition of Grignard Reagents to Chiral α-Ketoimides Derived from Oppolzer′s Sultam. ChemInform. 2006; 37 (18):1.
Chicago/Turabian StyleK. Raszplewicz; L. Sikorska; Katarzyna Kiegiel; T. Balakier; Janusz Jurczak. 2006. "Diastereoselective Addition of Grignard Reagents to Chiral α-Ketoimides Derived from Oppolzer′s Sultam." ChemInform 37, no. 18: 1.
The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide 13 is presented.
Katarzyna Kiegiel; Tomasz Bałakier; Piotr Kwiatkowski; Janusz Jurczak. Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide. Tetrahedron: Asymmetry 2004, 15, 3869 -3878.
AMA StyleKatarzyna Kiegiel, Tomasz Bałakier, Piotr Kwiatkowski, Janusz Jurczak. Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide. Tetrahedron: Asymmetry. 2004; 15 (24):3869-3878.
Chicago/Turabian StyleKatarzyna Kiegiel; Tomasz Bałakier; Piotr Kwiatkowski; Janusz Jurczak. 2004. "Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide." Tetrahedron: Asymmetry 15, no. 24: 3869-3878.
Three isoprenoid diphosphate analogues of farnesyl diphosphate (FPP) where the diphosphate has been replaced by methylene diphosphonate and the negative charges masked by frangible pivaloyloxymethyl (POM) esters were prepared. Farnesyl methylenediphosphonate is a sub-micromolar substrate for protein farnesyl transferase. The tripivaloyloxymethyl esters of isoprenoid methylenediphosphonate have significantly increased lipophilicity and may act as important farnesyl diphosphate prodrugs.
Jerry M. Troutman; Kareem A.H. Chehade; Katarzyna Kiegiel; Douglas A. Andres; H. Peter Spielmann. Synthesis of acyloxymethyl ester prodrugs of the transferable protein farnesyl transferase substrate farnesyl methylenediphosphonate. Bioorganic & Medicinal Chemistry Letters 2004, 14, 4979 -4982.
AMA StyleJerry M. Troutman, Kareem A.H. Chehade, Katarzyna Kiegiel, Douglas A. Andres, H. Peter Spielmann. Synthesis of acyloxymethyl ester prodrugs of the transferable protein farnesyl transferase substrate farnesyl methylenediphosphonate. Bioorganic & Medicinal Chemistry Letters. 2004; 14 (19):4979-4982.
Chicago/Turabian StyleJerry M. Troutman; Kareem A.H. Chehade; Katarzyna Kiegiel; Douglas A. Andres; H. Peter Spielmann. 2004. "Synthesis of acyloxymethyl ester prodrugs of the transferable protein farnesyl transferase substrate farnesyl methylenediphosphonate." Bioorganic & Medicinal Chemistry Letters 14, no. 19: 4979-4982.
K. Raszplewicz; L. Sikorska; Katarzyna Kiegiel; Janusz Jurczak. Highly Diastereoselective Addition of Grignard Reagents to N-Glyoxyloyl-(2R)-bornane-10,2-sultam — Comparative Studies. ChemInform 2003, 34, 1 .
AMA StyleK. Raszplewicz, L. Sikorska, Katarzyna Kiegiel, Janusz Jurczak. Highly Diastereoselective Addition of Grignard Reagents to N-Glyoxyloyl-(2R)-bornane-10,2-sultam — Comparative Studies. ChemInform. 2003; 34 (7):1.
Chicago/Turabian StyleK. Raszplewicz; L. Sikorska; Katarzyna Kiegiel; Janusz Jurczak. 2003. "Highly Diastereoselective Addition of Grignard Reagents to N-Glyoxyloyl-(2R)-bornane-10,2-sultam — Comparative Studies." ChemInform 34, no. 7: 1.
Farnesylation is a posttranslational lipid modification in which a 15-carbon farnesyl isoprenoid is linked via a thioether bond to specific cysteine residues of proteins in a reaction catalyzed by protein farnesyltransferase (FTase). We synthesized analogues (3-6) of farnesyl pyrophosphate (FPP) to probe the range of modifications possible to the FPP skeleton which allow for efficient transfer by FTase. Photoaffinity analogues of FPP (5, 6) were prepared by substituting perfluorophenyl azide functional groups for the omega-terminal isoprene of FPP. Substituted anilines replace the omega-terminal isoprene in analogues 3 and 4. Compounds 3-5 were prepared by reductive amination of the appropriate anilines with 8-oxo-geranyl acetate, followed by ester hydrolysis, chlorination, and pyrophosphorylation. Additional substitution of three methylenes for the beta-isoprene of FPP gave photoprobe 6 in nine steps. Preparation of the analogues required TiCl(4)-mediated imine formation prior to NaBH(OAc)(3) reduction for anilines with a pK(a) < 1. The azide moiety was not affected by Ph(3)PCl(2) conversion of allylic alcohols 13-16 into corresponding chlorides 17-20. Analogues 3-6 are efficiently transferred to target N-dansyl-GCVLS peptide substrate by mammalian FTase. Comparison of analogue structures and kinetics of transfer to those of FPP reveals that ring fluorination and para substituents have little effect on the affinity of the analogue pyrophosphate for FTase and its transfer efficiency. These results are also supported with models of the analogue binding modes in the active site of FTase. The transferable azide photoprobe 5 photoinactivates FTase. Transferable analogues 5 and 6 allow the formation of appropriately posttranslationally modified photoreactive peptide probes of isoprene function.
Kareem A. H. Chehade; Katarzyna Kiegiel; Richard J. Isaacs; Jennifer S. Pickett; Katherine E. Bowers; Carol A. Fierke; Uglas A. Andres; H. Peter Spielmann. Photoaffinity Analogues of Farnesyl Pyrophosphate Transferable by Protein Farnesyl Transferase. Journal of the American Chemical Society 2002, 124, 8206 -8219.
AMA StyleKareem A. H. Chehade, Katarzyna Kiegiel, Richard J. Isaacs, Jennifer S. Pickett, Katherine E. Bowers, Carol A. Fierke, Uglas A. Andres, H. Peter Spielmann. Photoaffinity Analogues of Farnesyl Pyrophosphate Transferable by Protein Farnesyl Transferase. Journal of the American Chemical Society. 2002; 124 (28):8206-8219.
Chicago/Turabian StyleKareem A. H. Chehade; Katarzyna Kiegiel; Richard J. Isaacs; Jennifer S. Pickett; Katherine E. Bowers; Carol A. Fierke; Uglas A. Andres; H. Peter Spielmann. 2002. "Photoaffinity Analogues of Farnesyl Pyrophosphate Transferable by Protein Farnesyl Transferase." Journal of the American Chemical Society 124, no. 28: 8206-8219.
Addition of allyltrimethylsilane (3) to N-glyoxyloyl-(2R)-bomane:0,2-sultam (4) in the presence of Lewis acid afforded, in high diastereoselecti vity, adduct (2'S)-6 which, after recrystallization, was hydrogenated to give optically pure (S)-1,2-pentanediol (1).
Katarzyna Kiegiel; Piotr Prokopowicz; Janusz Jurczak. Diastereoselective Addition of Allyltrimethylsilane toN-Glyoxyloyl-(2R)-bornane-10,2-sultam. A new synthesis of (S)-1,2-Pentanediol. Synthetic Communications 1999, 29, 3999 -4005.
AMA StyleKatarzyna Kiegiel, Piotr Prokopowicz, Janusz Jurczak. Diastereoselective Addition of Allyltrimethylsilane toN-Glyoxyloyl-(2R)-bornane-10,2-sultam. A new synthesis of (S)-1,2-Pentanediol. Synthetic Communications. 1999; 29 (22):3999-4005.
Chicago/Turabian StyleKatarzyna Kiegiel; Piotr Prokopowicz; Janusz Jurczak. 1999. "Diastereoselective Addition of Allyltrimethylsilane toN-Glyoxyloyl-(2R)-bornane-10,2-sultam. A new synthesis of (S)-1,2-Pentanediol." Synthetic Communications 29, no. 22: 3999-4005.
The recent development of very effective chiral auxiliaries has led to the design of 10-N,N-dicyclohexylsulphamoyl-(R)-isoborneol, which is similar to Oppolzer's (2R)-bornane-10,2-sultam but less effective on account of a less rigid structure. 10-N,N-Dicyclohexylsulphamoyl-(R)-isobornyl glyoxylate was examined in Diels–Alder and organometallic addition reactions. The results obtained were compared with those achieved by application of N-glyoxyloyl-(2R)-bornane-10,2-sultam.
Anna Czapla; Artur Chajewski; Katarzyna Kiegiel; Tomasz Bauer; Zbigniew Wielogorski; Zofia Urbanczyk-Lipkowska; Janusz Jurczak. The asymmetric hetero-Diels–Alder reaction and addition of allylic organometallics to 10-N,N-dicyclohexylsulphamoyl-(2R)-isobornyl glyoxylate. Tetrahedron: Asymmetry 1999, 10, 2101 -2111.
AMA StyleAnna Czapla, Artur Chajewski, Katarzyna Kiegiel, Tomasz Bauer, Zbigniew Wielogorski, Zofia Urbanczyk-Lipkowska, Janusz Jurczak. The asymmetric hetero-Diels–Alder reaction and addition of allylic organometallics to 10-N,N-dicyclohexylsulphamoyl-(2R)-isobornyl glyoxylate. Tetrahedron: Asymmetry. 1999; 10 (11):2101-2111.
Chicago/Turabian StyleAnna Czapla; Artur Chajewski; Katarzyna Kiegiel; Tomasz Bauer; Zbigniew Wielogorski; Zofia Urbanczyk-Lipkowska; Janusz Jurczak. 1999. "The asymmetric hetero-Diels–Alder reaction and addition of allylic organometallics to 10-N,N-dicyclohexylsulphamoyl-(2R)-isobornyl glyoxylate." Tetrahedron: Asymmetry 10, no. 11: 2101-2111.