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Pregled bibliografske jedinice broj: 564884

Conformational analysis of sugar-peptide adducts in the solution state by NMR spectroscopy and molecular modelling


Jerić, Ivanka; Novak, Predrag; Vinković, Mladen; Horvat, Štefica
Conformational analysis of sugar-peptide adducts in the solution state by NMR spectroscopy and molecular modelling // Journal of chemical society, Perkin Transaction 2, (2001), 10; 1944-1950 doi:10.1039/b104239b (međunarodna recenzija, članak, znanstveni)


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Naslov
Conformational analysis of sugar-peptide adducts in the solution state by NMR spectroscopy and molecular modelling

Autori
Jerić, Ivanka ; Novak, Predrag ; Vinković, Mladen ; Horvat, Štefica

Izvornik
Journal of chemical society, Perkin Transaction 2 (1364-5471) (2001), 10; 1944-1950

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
NMR spectroscopy ; molecular modelling ; sugar–peptide adducts

Sažetak
A combined use of NMR spectroscopy and molecular modelling has enabled insight into conformational features of the novel sugar–peptide adducts 1–3. Cyclic neoglycopeptide 1, having the β--glucopyranose moiety which connects terminal parts of the Tyr-Pro-Phe sequence into a 14-membered ring, has been found in a rigid conformation with a sandwich-like arrangement of the proline residue flanked by the tyrosine and the phenylalanine side-chains. However, cyclic Tyr-Pro-Phe-Val-related Amadori compound 2, with an 18-membered glycopeptide ring, has shown more flexibility in the peptide backbone and amino acid side-chains. Nevertheless, mutarotation was obstructed and the 1-deoxy--fructofuranose moiety was found in the β configuration exclusively. The analysis of the Amadori compound 3, with an unsubstituted C-terminal of the Tyr-Pro-Phe-Val peptide, has revealed the presence of conformational isomers arising from trans–cis isomerism of the Tyr1-Pro2 peptide bond, while the 1-deoxy--fructose has been found in the β-pyranose form. The results presented here point towards peptide sequence-governed overall conformation of the studied neoglycopeptides.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
00980704

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Ivanka Jerić (autor)

Avatar Url Štefica Horvat (autor)

Avatar Url Mladen Vinković (autor)

Avatar Url Predrag Novak (autor)

Citiraj ovu publikaciju

Jerić, Ivanka; Novak, Predrag; Vinković, Mladen; Horvat, Štefica
Conformational analysis of sugar-peptide adducts in the solution state by NMR spectroscopy and molecular modelling // Journal of chemical society, Perkin Transaction 2, (2001), 10; 1944-1950 doi:10.1039/b104239b (međunarodna recenzija, članak, znanstveni)
Jerić, I., Novak, P., Vinković, M. & Horvat, Š. (2001) Conformational analysis of sugar-peptide adducts in the solution state by NMR spectroscopy and molecular modelling. Journal of chemical society, Perkin Transaction 2, (10), 1944-1950 doi:10.1039/b104239b.
@article{article, year = {2001}, pages = {1944-1950}, DOI = {10.1039/b104239b}, keywords = {NMR spectroscopy, molecular modelling, sugar–peptide adducts}, journal = {Journal of chemical society, Perkin Transaction 2}, doi = {10.1039/b104239b}, number = {10}, issn = {1364-5471}, title = {Conformational analysis of sugar-peptide adducts in the solution state by NMR spectroscopy and molecular modelling}, keyword = {NMR spectroscopy, molecular modelling, sugar–peptide adducts} }
@article{article, year = {2001}, pages = {1944-1950}, DOI = {10.1039/b104239b}, keywords = {NMR spectroscopy, molecular modelling, sugar–peptide adducts}, journal = {Journal of chemical society, Perkin Transaction 2}, doi = {10.1039/b104239b}, number = {10}, issn = {1364-5471}, title = {Conformational analysis of sugar-peptide adducts in the solution state by NMR spectroscopy and molecular modelling}, keyword = {NMR spectroscopy, molecular modelling, sugar–peptide adducts} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • SCI-EXP, SSCI i/ili A&HCI


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