Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP)
Antifreeze glycoproteins are a class of biological agents which enable living at temperatures below the freezing point of the body fluids. Antifreeze glycopeptides usually consist of repeating tripeptide unit (-Ala-Ala-Thr*-), glycosylated at the threonine side chain. However, on the microscopic lev...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2019-07-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.15.162 |
| _version_ | 1819120303528214528 |
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| author | Małgorzata Urbańczyk Michał Jewgiński Joanna Krzciuk-Gula Jerzy Góra Rafał Latajka Norbert Sewald |
| author_facet | Małgorzata Urbańczyk Michał Jewgiński Joanna Krzciuk-Gula Jerzy Góra Rafał Latajka Norbert Sewald |
| author_sort | Małgorzata Urbańczyk |
| collection | DOAJ |
| description | Antifreeze glycoproteins are a class of biological agents which enable living at temperatures below the freezing point of the body fluids. Antifreeze glycopeptides usually consist of repeating tripeptide unit (-Ala-Ala-Thr*-), glycosylated at the threonine side chain. However, on the microscopic level, the mechanism of action of these compounds remains unclear. As previous research has shown, antifreeze activity of antifreeze glycopeptides strongly relies on the overall conformation of the molecule as well an on the stereochemistry of amino acid residues. The desired monoglycosylated analogues with acetylated amino termini and the carboxy termini in form of N-methylamide have been synthesized. Conformational nuclear magnetic resonance (NMR) studies of the designed analogues have shown a strong influence of the stereochemistry of amino acid residues on the peptide chain stability, which could be connected to the antifreeze activity of these compounds. A better understanding of the mechanism of action of antifreeze glycopeptides would allow applying these materials, e.g., in food industry and biomedicine. |
| first_indexed | 2024-12-22T06:18:31Z |
| format | Article |
| id | doaj.art-7a286044ae784040a11a3350617da7bd |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-22T06:18:31Z |
| publishDate | 2019-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-7a286044ae784040a11a3350617da7bd2022-12-21T18:36:01ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972019-07-011511581159110.3762/bjoc.15.1621860-5397-15-162Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP)Małgorzata Urbańczyk0Michał Jewgiński1Joanna Krzciuk-Gula2Jerzy Góra3Rafał Latajka4Norbert Sewald5Department of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wybrzeże Wyspianskiego 27, Wroclaw, PL-50-370, PolandDepartment of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wybrzeże Wyspianskiego 27, Wroclaw, PL-50-370, PolandDepartment of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wybrzeże Wyspianskiego 27, Wroclaw, PL-50-370, PolandDepartment of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wybrzeże Wyspianskiego 27, Wroclaw, PL-50-370, PolandDepartment of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wybrzeże Wyspianskiego 27, Wroclaw, PL-50-370, PolandOrganic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, Universitätsstraße 25, Bielefeld, D-33615, GermanyAntifreeze glycoproteins are a class of biological agents which enable living at temperatures below the freezing point of the body fluids. Antifreeze glycopeptides usually consist of repeating tripeptide unit (-Ala-Ala-Thr*-), glycosylated at the threonine side chain. However, on the microscopic level, the mechanism of action of these compounds remains unclear. As previous research has shown, antifreeze activity of antifreeze glycopeptides strongly relies on the overall conformation of the molecule as well an on the stereochemistry of amino acid residues. The desired monoglycosylated analogues with acetylated amino termini and the carboxy termini in form of N-methylamide have been synthesized. Conformational nuclear magnetic resonance (NMR) studies of the designed analogues have shown a strong influence of the stereochemistry of amino acid residues on the peptide chain stability, which could be connected to the antifreeze activity of these compounds. A better understanding of the mechanism of action of antifreeze glycopeptides would allow applying these materials, e.g., in food industry and biomedicine.https://doi.org/10.3762/bjoc.15.162antifreeze glycopeptidesconformational preferencesNMRPP IIsolid phase synthesis |
| spellingShingle | Małgorzata Urbańczyk Michał Jewgiński Joanna Krzciuk-Gula Jerzy Góra Rafał Latajka Norbert Sewald Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP) Beilstein Journal of Organic Chemistry antifreeze glycopeptides conformational preferences NMR PP II solid phase synthesis |
| title | Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP) |
| title_full | Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP) |
| title_fullStr | Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP) |
| title_full_unstemmed | Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP) |
| title_short | Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP) |
| title_sort | synthesis and conformational preferences of short analogues of antifreeze glycopeptides afgp |
| topic | antifreeze glycopeptides conformational preferences NMR PP II solid phase synthesis |
| url | https://doi.org/10.3762/bjoc.15.162 |
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