Synthesis and spectroscopic studies on turn structured models  Page description

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Details of project

 
Identifier
37719
Type K
Principal investigator Deckerné dr. Majer, Zsuzsanna
Title in Hungarian Turn szerkezeti elemeket tartalmazó modell vegyületek szintézise és spektroszkópiai jellemzése (cirkuláris dikroizmus - CD, vibrációs spektroszkópia - FTIR, mágneses rezonancia - NMR)
Title in English Synthesis and spectroscopic studies on turn structured models
Panel Chemistry 2
Department or equivalent Institute of Chemistry (Eötvös Loránd University)
Participants Radics, Gábor
Samu, János
Sewald, Norbert
Vass, Elemér
Starting date 2002-01-01
Closing date 2005-12-31
Funding (in million HUF) 8.870
FTE (full time equivalent) 0.00
state closed project





 

Final report

 
Results in Hungarian
A kanyarszerkezetek spektroszkópiai vizsgálatára választott ciklopeptid modellekben egy α-aminosavat kicseréltünk a megfelelő β-aminosavra és az így bekövetkezett konformációváltozást mértük. N-védett α-aminosavból Arndt-Eistert lánchosszabbítással enantiomer-tisztán előállítható a N-védett β3-aminosav (β-homo-aminosav). β-homo-aminosav tartalmú ciklotetra-, ciklopenta- és ciklohexapeptidek sorozatát állítottuk elő szilárd fázisú szintézissel, a ciklizációt oldatfázisban végezve. A vegyületeket HPLC-vel tisztítottuk és FAB-, illetve ESI-MS mérések alapján azonosítottuk.A modelleket és ezek kation-kötő képességét különböző oldószerekben vizsgáltuk CD- és FTIR-spektroszkópiával; néhány vegyületet NMR-spektroszkópiai adatokkal is jellemeztünk. A CD/FTIR spektroszkópiai analízis eredményei a következők:  a kis gyűrűméretű, erősen feszült ciklotetrapeptideknél a β-aminosavegységek jelenléte a szomszédos α-aminosavegységek körül γ-kanyart (C7) indukált  a ciklopentapeptidekél a β-homo-aminosavegység hajlékonyabb peptidgerincet biztosít és pszeudo-β-, vagy pszeudo-γ-kanyarok jönnek létre a β-aminosavegység körül.  CD/FTIR adataink segítségével a γ- és pszeudo-γ-kanyarszerkezet különböző oldószerekben jól jellemezhető. Több oligopeptid térszerkezetvizsgálatánál használtuk eredményesen a CD/FTIR komplex spektroszkópiai módszert.
Results in English
Cyclic peptides in which one α-amino acid is replaced by its β-amino acid analogy are also suitable for the conformational investigation of turn structures induced by β-amino acids in cyclic peptides. Enantiomerically pure β3-amino acids (β-homo-amino acids) were prepared from N-protected α-amino acids by Arndt-Eistert homologation reaction. A series of cyclic tetra-, penta- and hexapeptides containing β3-amino acid residue was synthesized on solid phase, cyclized in solution phase, purified by HPLC and characterised with FAB- and ESI-MS. The models and their cation-binding ability were investigated systematically by FTIR and CD spectroscopy in different solvents; some of them were studied by NMR spectroscopy, too. The combined CD/FTIR studies clearly show the followings:  the cyclic tetrapeptides are small and rather rigid molecules where the β-homo-amino acid residue induces a γ-turn (C7) which is centered on the neighbouring α-amino acid(s).  cyclic pentapeptides with β-homo-amino acid give rise to a more flexible peptide backbone and measured pseudo-β-turn or pseudo-γ-turns, which centered on the β-homo-amino acid.  the γ- and pseudo-γ-turn are well characterized in different solvents using CD- and FTIR spectroscopy. We investigated also the secondary structure of biologically active oligopeptides by combined CD/FTIR method.
Full text http://real.mtak.hu/322/
Decision
Yes





 

List of publications

 
Mező G; Majer Zs; Vass E; Jimenez M.A; Andreu D; Hudecz F.: Conformational study of linear and cyclic peptides corresponding to the 276-284 epitope region of HSV gD-1, Biophys Chem 103: 51-65, 2003
Vass E; Majer Zs; Sewald N; Hollósi M: Spectroscopic investigations on gamma-turn model cyclic peptides containing beta-amino acids, In: XXVI European Congress on Molecular Spectroscopy, France, 2002
Bősze Sz; Caccamo N; Majer Zs; Dieli F; Mező G; Hudecz F: Synthesis and in vitro T cell immunogenecity of oligopeptides corresponding to the 91-110 region of 16 kDa protein of Mycobacterium tuberculosis, In: Ettore Benedetti and Carlo Pedone (eds.), Peptides 2002, Edizioni Ziino, pp512-13, 2002
Windberg E; Majer Zs; Sebestyén F; Vass E; Hudecz F: The effect of non-native flanking sequences on antibody recognition and solution conformation of PTGTQ epitope from mucin-2, In: Ettore Benedetti and Carlo Pedone (eds.) Peptides 2002, Edizioni Ziino, pp. 920-1, 2002
Majer Zs; Farkas V; Kőhalmi K; Vass E; Vanhooren A; Hanssens I: Model cyclic peptides for studying the influence of ion cluster in the protein folding and stability, In: Ettore Benedetti and Carlo Pedone (eds.) Peptides 2002, Edizioni Ziino, pp. 800-1, 2002
Majer Zs; Bősze Sz; Mező G; Hudecz F: Conformational studies of oligopeptides corresponding to the 91-104 region of the 16 kDa protein of Mycobacterium tuberculosis, 8th International Conference on Circular Dichroism in Chemistry and Life Sciences, Budapest, p.124., 2003
Bősze Sz; Caccamo N; Majer Zs; Mező G; Dieli F; Hudecz F: T cell immunogenicity of oligopeptides with 91-106 epitope core of 16 kda protein of Mycobacterium tuberculosis and Ala flanks., In: Michael Chorev & Tom K. Sawyer (eds.) American Peptid Society, Peptide Revolution: Genomics, Proteomics and Therapeutics. pp.1001-2., 2003
Kőhidai L; Kun L; Pállinger É; Csaba Gy; Mihala N; Majer Zs; Süli-Varga H: Cell-physiological effects of elastin derived (VGVAPG)n oligomers in a unicellular model system, J. Pept. Sci. 10: 427-438, 2004
Mező G; Kalászi A; Reményi J; Majer Zs; Hilbert Á; Láng O; Kőhidai L; Barna K; Gaál R; Hudecz F: Synthesis, Conformation, and Immunoreactivity of New carrier molecules based on Repeated Tuftsin-Like Sequence, Biopolymers 73: 645-656, 2004
Vass E; Kőhalmi K; Hollósi M; Majer Zs: Spectroscopic investigations on model cyclic peptides containing beta-amino acids, J Pept Sci 10 (Supl.): 275, 2004
Vass E; Hollósi M; Besson F; Buchet R: Vibrational Spectroscopic Detection of Beta- and Gamma-Turns in Synthetic and natural peptides and Proteins, Chem Rev 103: 1917-1954, 2003
Malesevic M.; Majer Zs.; Vass E.; Huber, T.; Strijowski, U.; Hollósi, M.; Sewald N.;: Spectroscopic Detection of Pseudo-Turns in Homodetic Cyclic Penta- and Hexapeptides Comprising β-Homoproline, Int. J. Peptide Research and Therapeutics, in press, 2006
Shanmugam, G.; Polavarapu, P. L.; Hallgas, B.; Majer, Zs.: Effect of D-amino acids at Asp23 and Ser26 residues on the conformational preference of A-beta20-29 peptides, Biochem., Biophys. Res. Comm. 335, 712-722, 2005
Farkas V., Vass E., Hanssens I., Majer Zs., Hollósi M.: Cyclic peptide models of the Ca2+-binding loop of α-lactalbumin, Bioorganic & Medicinal Chemistry, 13, 5310-5320, 2005
Vanhooren A., Chedad A., Farkas V., Majer Z., Joniau M.,Van Dael H., Hanssens I.: Tryptophan to phenylalanine substitutions allow differetiation of short- and long-range conformational changes during denaturation of goat α-lactalbumin, PROTEINS: Structure, Function, and Bioinformatics, 60, 118-130, 2005
Volpon L.; Tsan P.; Majer Zs.; Vass E.; Hollósi M.; Noguéra V.; Lancelin J.-M.;: NMR structure determination of a synthetic analogue of bacillomycin L reveals the strategic role of L-Asn1 in the natural iturinic antibiotics, Journal of Peptide Science , in press, 2006
Buhlert J., Carle R., Majer Zs., Spitzner D.: Kann Acrylamid aus Peptiden entstehen? Eine Modellstudie, Letter in Organic Chemistry, accepted, 2006
MICHA J., KARLHEINZ A., MAJERZS., SEWALD N.: Synthesis of Efrapeptin C, In Peptides 2002, Ettore Benedetti and Carlo Pedone (Eds.), Edizioni Ziino, pp. 154-5, 2002
Bősze Sz; Caccamo N.; Majer Zs; Mező G; Dieli F.; Hudecz F.: In vitro T-cell immunogenicity of oligopeptides Derived from the region 92-110 of the 16kDa protein of Mycobacterium tuberculosis, Biopolymers, 76, 464-476,, 2004
Hollender, D., Kárply-Lakatos, A., Forgó, P., Körtvélyes, T., Dombi, Gy., Majer, Zs., Hollósi, M., Kiss, T., Odani, A.: Al(III)-binding ability of an octapeptide and its phosphorylated derivative, Journal of Inorganic Biochemistry, 100., 351-361, 2006




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