Application of chiroptical spectroscopy in the structural analysis of organic compounds  Page description

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Details of project

 
Identifier
43536
Type F
Principal investigator Kurtán, Tibor
Title in Hungarian Kiroptikai spektroszkópia alkalmazása a szerves vegyületek szerkezetvizsgálatában
Title in English Application of chiroptical spectroscopy in the structural analysis of organic compounds
Panel Chemistry 2
Department or equivalent Department of Organic Chemistry (University of Debrecen)
Participants Ferenczi, Renáta
Starting date 2003-01-01
Closing date 2007-06-30
Funding (in million HUF) 4.384
FTE (full time equivalent) 0.00
state closed project





 

Final report

 
Results in Hungarian
Az ifjúsági OTKA pályázat keretében elért eredmények az alábbi három fő témakör köré csoportosíthatók: I) O-heterociklusok és szénhidrát származékok enantioszelektív szintézise és sztereo-kémiájuk vizsgálata kiroptikai spektroszkópiával. Ezen belül az alábbi vegyületeket vizsgáltuk: 1) cis és trans-pterokarpánok 2) dioxán típusú (2-naftil)metil acetál védőcsoportokat tartalmazó glükozidok és galaktozidok 3) S-S vagy Se-Se kötést tartalmazó dikalkogenid-diszacharidok 4) Silybum marianum L. flavanolignán komponensei 5) szintetikus optikailag aktív 1,4-benzodioxánok 6) izopropilidén guanozin telekelikus dimerje 7) szubszituált 4H-benzopirán (kromán) és 2,3-dihidroizokumarin származékok II) Izolált és szintetikus flavonoid származékok abszolút konfigurációjának meghatározása online HPLC-CD technikával. Az alábbi vegyületcsoportokat vizsgáltuk: 1) izolált 2,8”-biflavanoid izomerek 2) szintetikus eritro és treo-8.4’-oxineolignének 3) izolált 2-metilkromanon származékok III) Izolált természetes anyagok abszolút konfigurációjának meghatározására egy új szilárd fázisú TDDFT/CD módszert vezettünk be. Az alábbi természetes anyagok abszolút konfigurációját határoztuk meg: 1) plumericin és isoplumericin 2) xyloketal F 3) phomoxanthone A 4) globusoxanthone A 5) ascochin 6) massarilactone E 7) tetrahidropyrenophorol 8) hypothemycin 9) palmarumycin és papyracillic sav A kutatás eredményeként 23 angol nyelvű folyóiratcikket publikáltunk, egy cikket közlésre fogadtak el és egyet közlésre nyújtottunk be.
Results in English
The scientific results achieved in the frame of the young scientist OTKA grant can be grouped around the following three major topics: I) Enantioselective synthesis of O-heterocycles and carbohydrates and the study of their stereochemistry by chiroptical spectroscopy. In this topic, the following compounds were investigated: 1) cis- and trans-pterocarpans 2) glycosides and galactosides containing dioxane-type (2-naphthyl)methyl acetal protecting groups 3) dichalcogenide disaccharides containing S-S or Se-Se bonds 4) flavanolignan constituents of Silybum marianum L. 5) synthetic optically active 1,4-benzodioxanes 6) telechelic dimmer of isopropylidene guanosine 7) substituted 4H-benzopyran (chromane) and 2,3-dihydroisocoumarine derivatives II) Configurational assignment of isolated and synthetic flavonoid derivatives by online HPLC-CD technique. The following types of compounds were studied: 1) isolated 2,8”-biflavanoid isomers 2) synthetic erithro- and treo-8.4’-oxyneolignenes 3) isolated 2-methylchromanone derivatives II) For the configurational assignment of isolated natural products, a novel solid-state TDDFT/CD method was introduced. The absolute configuration of the following natural products were deduced: 1) plumericin and isoplumericin 2) xyloketal F 3) phomoxanthone A 4) globusoxanthone A 5) ascochin 6) massarilactone E 7) tetrahydropyrenophorol 8) hypothemycin 9) palmarumycin and papyracillic acid As a result of the research, 23 scientific English journal articles were published, one paper has been accepted for publication and one has just been submitted.
Full text http://real.mtak.hu/1121/
Decision
Yes





 

List of publications

 
Wu XY; Liu XH; Lin YC; Luo JH; She ZG; Houjin L; Chan WL; Antus S; Kurtán T; Elsässer B; Krohn K: Xyloketal F: A Strong L-Calcium Channel Blocker from the Mangrove Fungus Xylaria sp. (#2508) from the South China Sea Coast., Eur J Org Chem 4061-4064, 2005
Elsässer B; Krohn K; Akhtar MN; Flörke U; Kouam SF; Kuigoua MG; Ngadjui BT; Abegaz BM; Antus S; Kurtán T: Revision of the Absolute Configurations of Plumericin and Isoplumericin from Plumeria rubra, Chemistry & Biodiversity 2(6): 799-808, 2005
Kiss L; Kurtán T; Antus S; Brunner H: Further insight into the mechanism of Heck oxyarylation in the presence of chiral ligand, Arkivoc 5: 69-76, 2003
Kiss L; Kurtán T; Antus S; Bényei A: Chiroptical properties and synthesis of enantiopure cis and trans pterocarpan skeleton, Chirality 6(15): 558-563, 2003
Antus S; Gulácsi K; Juhász L; Kiss L; Kurtán T: Synthesis of naturally occurring O-heterocyclic compounds of biological activity, Pure Appl Chem 76(5): 1025-1032, 2004
Samu Zs; Nyiredy Sz; Baitz-Gács E; Varga Zs; Kurtán T; Dinya Z; Antus S: Strucutre elucidation and antioxidant activity of (-)-isosilandrin isolated from Silybum marianum L, Chemistry & Biodiversity 1(11): 1668-1677, 2004
Kónya K; Kurtán T; Kiss-Szikszai A; Juhász L; Antus S: A general CD method for the configurational assignment of erythro-8.O.4'-neolignans, Arkivoc 13; 72-78, 2004
Ferenczi R; Kurtán T; Dinya Z; Antus S: Synthesis of deuterium labelled silybin and isosilybin, Heterocycl Commun 11: 491-494, 2005
Krohn K; Ullah Z; Flörke U; Schulz B; Draeger S; Pescitelli G; Salvadori P; Antus S; Kurtán T: Massarilactones E-G, New Metabolites from the Endophytic Fungus Coniothyrium sp., associated with the Plant Artimisia maritima, Chirality 19: 464-470, 2007
Pintér G; Batta Gy; Horváth P; Löki I; Kurtán T; Antus S; Kéki S; Zsuga M; Nagy G; Aradi J; Gunda T; Herczegh P: Supramolecular polymers based on the quadruplex formation of ditopic guanosine macromonomers in nonaqueous media, Langmuir 23: 5283-5285, 2007
Hussain H; Krohn K; Flörke U; Schulz B; Draeger S; Pescitelli G; Salvadori P; Antus S; Kurtán T: Absolute configuration of hypothemycin and 5'-O-methylhypothemycin from Phoma sp. - A test case for solid state CD/TDDFT approach, Tetrahedron: Asymm 18: 925-930, 2007
Dai J; Krohn K; Elsasser B; Flörke U; Draeger S; Schulz B; Pescitelli G; Salvadori P; Antus S; Kurtán T: Metabolic products of the endophytic fungus Microsphaeropsis sp. from Larix decidua, Eur J Org Chem online közölve DOI:10.1002/ejoc.200700348, 2007
Kurtán T; Pescitelli G; Salvadori P; Kenéz Á; Antus S; Illyés TZ; Szilágyi L; Szabó I: Circular dichroism of diglycosyl dichalcogenides in solution and solid state, Chirality online közölve, DOI: 10.1002/chir.20458, 2007
Nyiredy Sz; Szűcs Z; Fatér Zs; Gulácsi K; Kurtán T; Antus S: New insight into the biosynthesis of flavanolignans in the white-flowered variant of Silybum marianum, J Chromatogr Sci (közlésre elfogadva), 2007
Kónya K; Ferenczi R; Czompa A; Kiss-Szikszai A; Kurtán T; Antus S: Kinetic resolution of 2-hydroxymethyl-1,4-benzodioxanes by Pseudomonas flurescens, Arkivoc (közlésre elküldve), 2007
Ferrari J; Terreaux T; Kurtán T; Kiss ASz; Antus S; Msonthi JD; Hostettmann K: Isolation and on-line LC/CD analysis of 3,8"-linked biflavanoids from Gnidia involucrata, Helv Chim Acta 86: 2768-2778, 2003
Kurtán T; Borbás A; Szabó ZB; Lipták A; Bényei A; Antus S: Circular dichroism of 1,3-dioxane-type (2'-naphthyl)methylene acetals of glycosides, Chirality 16(4): 244-250, 2004
Kónya K; Kiss-Szikszai A; Kurtán T; Antus S: Enantiomeric separation of racemic neolignans on Chiralcel OD and determination of their absolute configuration with online circular dichroism, J Chromatogr Sci 42(9): 478-483, 2004
Elsässer B; Krohn K; Flörke U; Root N; Aust HJ; Draeger S; Schulz B; Antus S; Kurtán T: X-ray structure determination, absolute configuration and biological activity of phomoxanthone A, Eur J Org Chem 4563-4570, 2005
Dai J; Krohn K; Flörke U; Draeger S; Schulz B; Kiss-Szikszai A; Antus S; Kurtán T; Ree T: Metabolites from the Endophytic Fungus Nodulisporium sp. from Juniperus cedre., Eur J Org Chem 3498-3506, 2006
Hussain H; Krohn K; Flörke U; Schulz B; Draeger S; Pescitelli G; Antus S; Kurtán T: Absolute Configuration of Globosuxanthone A and Secondary Metabolites from Microdiplodia sp. - A novel solid-state CD / TDDFT approach., Eur J Org Chem 292-295, 2007
Kerti G; Kurtán T; Illyés TZ; Kövér KE; Sólyom S; Pescitelli G; Fujioka N; Berova N; Antus S: Enantioselective synthesis of 3-methylisochromans and determination of their absolute configurations by circular dichroism., Eur J Org Chem 296-305, 2007
Stephens PJ; Pan JJ; Devlin FJ; Krohn K; Kurtán T: Determination of the absolute configurations of natural products via density functional theory calculations of vibrational circular dichroism, electronic circular dichroism, and optical rotation: The iridoids plumericin and isoplumericin, J Org Chem 72(9): 3521-3536, 2007
Krohn K; Farooq U; Flörke U; Schulz B; Draeger S; Pescitelli G; Salvadori P; Antus S; Kurtán T: Secondary metabolites isolated from an endophytic Phoma sp. - Absolute configuration of tetrahydropyrenophorol using the solid-state TDDFT CD methodology, Eur J Org Chem 3206-3211, 2007
Krohn K; Kock I; Elsasser B; Flörke U; Schulz B; Draeger S; Pescitelli G; Antus S; Kurtán T: Bioactive natural products from the endophytic fungus Ascochyta sp. from Meliotus dentatus – configurational assignment by solid-state CD and TDDFT calculations., Eur J Org Chem 1123-1129, 2007




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