VCD studies on cyclic peptides assembled from L-alpha-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid
Vass E, Strijowski U, Wollschlaeger K, Mandity IM, Szilvagyi G, Jewginski M, Gaus K, Royo S, Majer Z, Sewald N, Hollosi M (2010)
Journal of Peptide Science 16(11): 613-620.
Zeitschriftenaufsatz
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Autor*in
Vass, E.;
Strijowski, U.;
Wollschlaeger, K.;
Mandity, I. M.;
Szilvagyi, G.;
Jewginski, M.;
Gaus, K.;
Royo, S.;
Majer, Z.;
Sewald, NorbertUniBi ;
Hollosi, M.
Einrichtung
Abstract / Bemerkung
The increasing interest in peptidomimetics of biological relevance prompted us to synthesize a series of cyclic peptides comprising trans-2-aminocyclohexane carboxylic acid (Achc) or trans-2-aminocyclopentane carboxylic acid (Acpc). NMR experiments in combination with MD calculations were performed to investigate the three-dimensional structure of the cyclic peptides. These data were compared to the conformational information obtained by electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopy. Experimental VCD spectra were compared to theoretical VCD spectra computed quantum chemically at B3LYP/6-31G(d) density functional theory (DFT) level. The good agreement between the structural features derived from the VCD spectra and the NMR-based structures underlines the applicability of VCD in studying the conformation of small cyclic peptides. Copyright 2010 European Peptide Society and John Wiley & Sons, Ltd.
Stichworte
cyclic peptides;
electronic circular dichroism;
NMR;
vibrational circular dichroism;
carboxylic acid;
trans-2-aminocyclohexane carboxylic acid;
trans-2-aminocyclopentane
Erscheinungsjahr
2010
Zeitschriftentitel
Journal of Peptide Science
Band
16
Ausgabe
11
Seite(n)
613-620
ISSN
1075-2617
Page URI
https://pub.uni-bielefeld.de/record/1929269
Zitieren
Vass E, Strijowski U, Wollschlaeger K, et al. VCD studies on cyclic peptides assembled from L-alpha-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid. Journal of Peptide Science. 2010;16(11):613-620.
Vass, E., Strijowski, U., Wollschlaeger, K., Mandity, I. M., Szilvagyi, G., Jewginski, M., Gaus, K., et al. (2010). VCD studies on cyclic peptides assembled from L-alpha-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid. Journal of Peptide Science, 16(11), 613-620. https://doi.org/10.1002/psc.1272
Vass, E., Strijowski, U., Wollschlaeger, K., Mandity, I. M., Szilvagyi, G., Jewginski, M., Gaus, K., et al. 2010. “VCD studies on cyclic peptides assembled from L-alpha-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid”. Journal of Peptide Science 16 (11): 613-620.
Vass, E., Strijowski, U., Wollschlaeger, K., Mandity, I. M., Szilvagyi, G., Jewginski, M., Gaus, K., Royo, S., Majer, Z., Sewald, N., et al. (2010). VCD studies on cyclic peptides assembled from L-alpha-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid. Journal of Peptide Science 16, 613-620.
Vass, E., et al., 2010. VCD studies on cyclic peptides assembled from L-alpha-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid. Journal of Peptide Science, 16(11), p 613-620.
E. Vass, et al., “VCD studies on cyclic peptides assembled from L-alpha-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid”, Journal of Peptide Science, vol. 16, 2010, pp. 613-620.
Vass, E., Strijowski, U., Wollschlaeger, K., Mandity, I.M., Szilvagyi, G., Jewginski, M., Gaus, K., Royo, S., Majer, Z., Sewald, N., Hollosi, M.: VCD studies on cyclic peptides assembled from L-alpha-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid. Journal of Peptide Science. 16, 613-620 (2010).
Vass, E., Strijowski, U., Wollschlaeger, K., Mandity, I. M., Szilvagyi, G., Jewginski, M., Gaus, K., Royo, S., Majer, Z., Sewald, Norbert, and Hollosi, M. “VCD studies on cyclic peptides assembled from L-alpha-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid”. Journal of Peptide Science 16.11 (2010): 613-620.
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3 Zitationen in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
Vibrational circular dichroism of a 2,5-diketopiperazine (DKP) peptide: Evidence for dimer formation in cyclo LL or LD diphenylalanine in the solid state.
Pérez-Mellor A, Zehnacker A., Chirality 29(2), 2017
PMID: 28079923
Pérez-Mellor A, Zehnacker A., Chirality 29(2), 2017
PMID: 28079923
Induced folding of protein-sized foldameric β-sandwich models with core β-amino acid residues.
Olajos G, Hetényi A, Wéber E, Németh LJ, Szakonyi Z, Fülöp F, Martinek TA., Chemistry 21(16), 2015
PMID: 25677195
Olajos G, Hetényi A, Wéber E, Németh LJ, Szakonyi Z, Fülöp F, Martinek TA., Chemistry 21(16), 2015
PMID: 25677195
α/β-Peptide foldamers: state of the art.
Pilsl LK, Reiser O., Amino Acids 41(3), 2011
PMID: 21462000
Pilsl LK, Reiser O., Amino Acids 41(3), 2011
PMID: 21462000
43 References
Daten bereitgestellt von Europe PubMed Central.
The world of beta- and gamma-peptides comprised of homologated proteinogenic amino acids and other components.
Seebach D, Beck AK, Bierbaum DJ., Chem. Biodivers. 1(8), 2004
PMID: 17191902
Seebach D, Beck AK, Bierbaum DJ., Chem. Biodivers. 1(8), 2004
PMID: 17191902
Asymmetric synthesis of β-amino acids and α-substituted β-amino acids
Cardillo, Chem. Soc. Rev. 25(), 1996
Cardillo, Chem. Soc. Rev. 25(), 1996
The twists and turns of beta-peptides.
DeGrado WF, Schneider JP, Hamuro Y., J. Pept. Res. 54(3), 1999
PMID: 10517158
DeGrado WF, Schneider JP, Hamuro Y., J. Pept. Res. 54(3), 1999
PMID: 10517158
Helices and other secondary structures of beta- and gamma-peptides.
Seebach D, Hook DF, Glattli A., Biopolymers 84(1), 2006
PMID: 16235225
Seebach D, Hook DF, Glattli A., Biopolymers 84(1), 2006
PMID: 16235225
Structure and conformation of β-oligopeptide derivatives with simple proteinogenic side chains: circular dichroism and molecular dynamics investigations
Seebach, Helv. Chim. Acta 83(), 2000
Seebach, Helv. Chim. Acta 83(), 2000
Basic conformers in beta-peptides.
Mohle K, Gunther R, Thormann M, Sewald N, Hofmann HJ., Biopolymers 50(2), 1999
PMID: 10380341
Mohle K, Gunther R, Thormann M, Sewald N, Hofmann HJ., Biopolymers 50(2), 1999
PMID: 10380341
β-Peptide foldamers: robust helix formation in a new family of β-amino acid oligomers
Appella, J. Am. Chem. Soc. 118(), 1996
Appella, J. Am. Chem. Soc. 118(), 1996
Synthesis and conformational analysis of linear and cyclic peptides containing sugar amino acids
Graf, J. Am. Chem. Soc. 118(), 1996
Graf, J. Am. Chem. Soc. 118(), 1996
Are β-amino acids γ-turn mimetics? Exploring a new design principle for bioactive cyclopeptides
Schumann, J. Am. Chem. Soc. 122(), 2000
Schumann, J. Am. Chem. Soc. 122(), 2000
The outstanding biological stability of beta- and gamma-peptides toward proteolytic enzymes: an in vitro investigation with fifteen peptidases.
Frackenpohl J, Arvidsson PI, Schreiber JV, Seebach D., Chembiochem 2(6), 2001
PMID: 11828476
Frackenpohl J, Arvidsson PI, Schreiber JV, Seebach D., Chembiochem 2(6), 2001
PMID: 11828476
Protein prosthesis: a semisynthetic enzyme with a beta-peptide reverse turn.
Arnold U, Hinderaker MP, Nilsson BL, Huck BR, Gellman SH, Raines RT., J. Am. Chem. Soc. 124(29), 2002
PMID: 12121081
Arnold U, Hinderaker MP, Nilsson BL, Huck BR, Gellman SH, Raines RT., J. Am. Chem. Soc. 124(29), 2002
PMID: 12121081
FR109615, a new antifungal antibiotic from Streptomyces setonii. Taxonomy, fermentation, isolation, physico-chemical properties and biological activity.
Iwamoto T, Tsujii E, Ezaki M, Fujie A, Hashimoto S, Okuhara M, Kohsaka M, Imanaka H, Kawabata K, Inamoto Y., J. Antibiot. 43(1), 1990
PMID: 2307620
Iwamoto T, Tsujii E, Ezaki M, Fujie A, Hashimoto S, Okuhara M, Kohsaka M, Imanaka H, Kawabata K, Inamoto Y., J. Antibiot. 43(1), 1990
PMID: 2307620
Foldamers: a manifesto
Gellman, Acc. Chem. Res. 31(), 1998
Gellman, Acc. Chem. Res. 31(), 1998
beta-Peptides: from structure to function.
Cheng RP, Gellman SH, DeGrado WF., Chem. Rev. 101(10), 2001
PMID: 11710070
Cheng RP, Gellman SH, DeGrado WF., Chem. Rev. 101(10), 2001
PMID: 11710070
The chemistry of 2-aminocycloalkanecarboxylic acids.
Fulop F., Chem. Rev. 101(7), 2001
PMID: 11710244
Fulop F., Chem. Rev. 101(7), 2001
PMID: 11710244
Side-chain control of β-peptide secondary structures: design principles
Martinek, Eur. J. Biochem. 270(), 2001
Martinek, Eur. J. Biochem. 270(), 2001
Application of alicyclic β-amino acids in peptide chemistry
Fülöp, Chem. Soc. Rev. 35(), 2009
Fülöp, Chem. Soc. Rev. 35(), 2009
Nucleo-β-amino acids: synthesis and oligomerization to β-homoalanyl-PNA
Brückner, Helv. Chim. Acta 85(), 2002
Brückner, Helv. Chim. Acta 85(), 2002
Sewald, 2009
Spectroscopic detection of Pseudo-turns in homodetic cyclic penta- and hexapeptides comprising β-homoproline
Maleševi', Int. J. Pept. Res. Ther. 12(), 2006
Maleševi', Int. J. Pept. Res. Ther. 12(), 2006
Improved treatment of cyclic β-amino acids and successful prediction of β-peptide secondary structure using a modified force field: AMBER*C
Christianson, J. Comput. Chem. 21(), 2000
Christianson, J. Comput. Chem. 21(), 2000
cis-2-aminocyclopentanecarboxylic acid oligomers adopt a sheetlike structure: switch from helix to nonpolar strand.
Martinek TA, Toth GK, Vass E, Hollosi M, Fulop F., Angew. Chem. Int. Ed. Engl. 41(10), 2002
PMID: 19750694
Martinek TA, Toth GK, Vass E, Hollosi M, Fulop F., Angew. Chem. Int. Ed. Engl. 41(10), 2002
PMID: 19750694
Vibrational circular dichroism: an incisive tool for stereochemical applications.
Nafie LA, Freedman TB., Enantiomer 3(4-5), 1998
PMID: 9861702
Nafie LA, Freedman TB., Enantiomer 3(4-5), 1998
PMID: 9861702
Vibrational circular dichroism and IR spectral analysis as a test of theoretical conformational modeling for a cyclic hexapeptide.
Bour P, Kim J, Kapitan J, Hammer RP, Huang R, Wu L, Keiderling TA., Chirality 20(10), 2008
PMID: 18506832
Bour P, Kim J, Kapitan J, Hammer RP, Huang R, Wu L, Keiderling TA., Chirality 20(10), 2008
PMID: 18506832
Frisch, 2004
Protein and peptide secondary structure and conformational determination with vibrational circular dichroism.
Keiderling TA., Curr Opin Chem Biol 6(5), 2002
PMID: 12413554
Keiderling TA., Curr Opin Chem Biol 6(5), 2002
PMID: 12413554
Vibrational spectroscopic detection of beta- and gamma-turns in synthetic and natural peptides and proteins.
Vass E, Hollosi M, Besson F, Buchet R., Chem. Rev. 103(5), 2003
PMID: 12744696
Vass E, Hollosi M, Besson F, Buchet R., Chem. Rev. 103(5), 2003
PMID: 12744696
Optical spectroscopic elucidation of β-turns in disulfide bridged cyclic tetrapeptides
Borics, Biopolymers 85(), 2006
Borics, Biopolymers 85(), 2006
IR (vibrational) CD of peptide β-turns: A theoretical and experimental study of cyclo-(-Gly-Pro-Gly-D-Ala-Pro-)
Wyssbrod, Biopolymers 31(), 1992
Wyssbrod, Biopolymers 31(), 1992
IR circular dichroism of turns in small peptides
Xie, Faraday Discuss. 99(), 1994
Xie, Faraday Discuss. 99(), 1994
Optical spectroscopic investigations of model beta-sheet hairpins in aqueous solution.
Hilario J, Kubelka J, Keiderling TA., J. Am. Chem. Soc. 125(25), 2003
PMID: 12812496
Hilario J, Kubelka J, Keiderling TA., J. Am. Chem. Soc. 125(25), 2003
PMID: 12812496
Vibrational circular dichroism of α-hairpin peptide
Zhao, J. Am. Chem. Soc. 122(), 2000
Zhao, J. Am. Chem. Soc. 122(), 2000
AUTHOR UNKNOWN, 0
Structural properties of cyclic peptides containing cis- or trans-2-aminocyclohexane carboxylic acid.
Strijowski U, Sewald N., Org. Biomol. Chem. 2(8), 2004
PMID: 15064783
Strijowski U, Sewald N., Org. Biomol. Chem. 2(8), 2004
PMID: 15064783
Asymmetric synthesis of (−)-(1R,2S)-cispentacin and related cis- and trans-2-amino cyclopentane- and cyclohexane-1-carboxylic acids
Davies, J. Chem. Soc. Perkin Trans. 1. (), 1994
Davies, J. Chem. Soc. Perkin Trans. 1. (), 1994
Improved purities for Fmoc-amino acids from Fmoc-ONSu
Milton, Int. J. Pept. Prot. Res. 30(), 1987
Milton, Int. J. Pept. Prot. Res. 30(), 1987
An improved method for the solution cyclization of peptides under pseudo-high dilution conditions.
Malesevic M, Strijowski U, Bachle D, Sewald N., J. Biotechnol. 112(1-2), 2004
PMID: 15288942
Malesevic M, Strijowski U, Bachle D, Sewald N., J. Biotechnol. 112(1-2), 2004
PMID: 15288942
The dependence of vicinal proton-proton coupling constants on dihedral angle and substituents
Pachler, J. Chem. Soc. Perkin Trans. 2. (), 1972
Pachler, J. Chem. Soc. Perkin Trans. 2. (), 1972
Secondary structure inducing potential of beta-amino acids: torsion angle clustering facilitates comparison and analysis of the conformation during MD trajectories.
Guthohrlein EW, Malesevic M, Majer Z, Sewald N., Biopolymers 88(6), 2007
PMID: 17922495
Guthohrlein EW, Malesevic M, Majer Z, Sewald N., Biopolymers 88(6), 2007
PMID: 17922495
The Xplor-NIH NMR molecular structure determination package.
Schwieters CD, Kuszewski JJ, Tjandra N, Clore GM., J. Magn. Reson. 160(1), 2003
PMID: 12565051
Schwieters CD, Kuszewski JJ, Tjandra N, Clore GM., J. Magn. Reson. 160(1), 2003
PMID: 12565051
An improved GROMOS96 force field for aliphatic hydrocarbons in the condensed phase
Schuler, J. Comput. Chem. 22(), 2001
Schuler, J. Comput. Chem. 22(), 2001
An effective force field for molecular dynamics simulations of dimethyl sulfoxide and dimethyl sulfoxide-water mixtures
Geerke, J. Phys. Chem. B. 108(), 2004
Geerke, J. Phys. Chem. B. 108(), 2004
Smoothing and differentiation of data by simplified least squares procedures
Savitzky, Anal. Chem. 36(), 1964
Savitzky, Anal. Chem. 36(), 1964
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