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dc.contributor.authorKijewska, Monika
dc.contributor.authorWaliczek, Mateusz
dc.contributor.authorCal, Marta
dc.contributor.authorJaremko, Lukasz
dc.contributor.authorJaremko, Mariusz
dc.contributor.authorKról, Maria
dc.contributor.authorKołodziej, Marta
dc.contributor.authorLisowski, Marek
dc.contributor.authorStefanowicz, Piotr
dc.contributor.authorSzewczuk, Zbigniew
dc.date.accessioned2018-09-03T13:19:02Z
dc.date.available2018-09-03T13:19:02Z
dc.date.issued2018-07-11
dc.identifier.citationKijewska M, Waliczek M, Cal M, Jaremko Ł, Jaremko M, et al. (2018) Solid-phase synthesis of peptides containing aminoadipic semialdehyde moiety and their cyclisations. Scientific Reports 8. Available: http://dx.doi.org/10.1038/s41598-018-28798-9.
dc.identifier.issn2045-2322
dc.identifier.doi10.1038/s41598-018-28798-9
dc.identifier.urihttp://hdl.handle.net/10754/628370
dc.description.abstractPathological levels of oxidative stress (OS) have been implicated in many diseases including diabetes mellitus, neurodegenerative diseases, inflammatory diseases, atherosclerosis, and cancer. Studies of oxidative stress are however complicated by the low concentration of oxidation products. To resolve this problem, we tested a new derivative of aminoadipic semialdehyde (Fmoc-Aea-OH) in the solid-phase synthesis of carbonylated peptides. We prepared a series of peptides with free and acetylated N-terminal amino groups using the Fmoc-Aea-OH reagent. LC-MS, ESI-MS, and MS/MS spectra confirmed the sequences of the modified peptides, although the LC-MS and ESI-MS spectra were dominated by signals corresponding to dehydration products. NMR studies of acetylated products revealed that the dominant product formed in this reaction contains a 1,2,3,4-tetrahydropyridine-2-carboxylic acid residue. Another side reaction in this system was the cleavage of the amide bond between the Aea residue and the amino acid moiety preceding it resulting in the formation of a side product with a six-membered ring at the N-terminus (2,3,4,5-tetrahydropyridine-2-carboxylic acid residue). We found that, depending on the peptide sequence, one of those side products is predominant. Our work suggests new methods for the solid-state synthesis of peptides containing unnatural amino acids.
dc.description.sponsorshipThis work was supported by a grant No UMO-2012/07/D/ST5/002324 from the Polish National Science Centre. M. J. and Ł. J would like to like to thank King Abdullah University of Science and Technology (KAUST) for financial support.
dc.publisherSpringer Nature
dc.relation.urlhttps://www.nature.com/articles/s41598-018-28798-9
dc.rightsThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.titleSolid-phase synthesis of peptides containing aminoadipic semialdehyde moiety and their cyclisations
dc.typeArticle
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Division
dc.contributor.departmentBioscience Program
dc.identifier.journalScientific Reports
dc.eprint.versionPublisher's Version/PDF
dc.contributor.institutionFaculty of Chemistry, University of Wrocław, Joliot-Curie 14, 50-383, Wrocław, Poland.
kaust.personJaremko, Lukasz
kaust.personJaremko, Mariusz
refterms.dateFOA2018-09-12T06:41:57Z
dc.date.published-online2018-07-11
dc.date.published-print2018-12


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This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
Except where otherwise noted, this item's license is described as This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.