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.

Download
Es wurde kein Volltext hochgeladen. Nur Publikationsnachweis!
Zeitschriftenaufsatz | Veröffentlicht | Englisch
Autor
; ; ; ; ; ; ; ; ; ;
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.
Erscheinungsjahr
Zeitschriftentitel
JOURNAL OF PEPTIDE SCIENCE
Band
16
Ausgabe
11
Seite(n)
613-620
ISSN
PUB-ID

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. doi:10.1002/psc.1272
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.

3 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

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
α/β-Peptide foldamers: state of the art.
Pilsl LK, Reiser O., Amino Acids 41(3), 2011
PMID: 21462000

43 References

Daten bereitgestellt von Europe PubMed Central.

Asymmetric synthesis of β-amino acids and α-substituted β-amino acids
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
Helices and other secondary structures of beta- and gamma-peptides.
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
Basic conformers in beta-peptides.
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
Synthesis and conformational analysis of linear and cyclic peptides containing sugar amino acids
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
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
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
Foldamers: a manifesto
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
The chemistry of 2-aminocycloalkanecarboxylic acids.
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
Application of alicyclic β-amino acids in peptide chemistry
Fülöp, Chem. Soc. Rev. 35(), 2009
Nucleo-β-amino acids: synthesis and oligomerization to β-homoalanyl-PNA
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
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
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
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

Frisch, 2004
Optical spectroscopic elucidation of β-turns in disulfide bridged cyclic tetrapeptides
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
IR circular dichroism of turns in small peptides
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
Vibrational circular dichroism of α-hairpin peptide
Zhao, J. Am. Chem. Soc. 122(), 2000

AUTHOR UNKNOWN, 0
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
Improved purities for Fmoc-amino acids from Fmoc-ONSu
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
The dependence of vicinal proton-proton coupling constants on dihedral angle and substituents
Pachler, J. Chem. Soc. Perkin Trans. 2. (), 1972
The Xplor-NIH NMR molecular structure determination package.
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
An effective force field for molecular dynamics simulations of dimethyl sulfoxide and dimethyl sulfoxide-water mixtures
Geerke, J. Phys. Chem. B. 108(), 2004
Smoothing and differentiation of data by simplified least squares procedures
Savitzky, Anal. Chem. 36(), 1964

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®

Quellen

PMID: 20848613
PubMed | Europe PMC

Suchen in

Google Scholar