<i>Ac</i>-[K-Aib-C(3,9-<i>Acm</i>; 6,12-DFLC<sub>(</sub><i><sub>Acm</sub></i><sub>)</sub>KKESEK)]<sub>4</sub>-<i>NH</i><sub>2</sub>
Chemoselective reactions have played a crucial role in the development of high-molecular-weight (>3000 Da) macromolecules with a branched architecture, particularly as peptides and epitope-based vaccines have emerged as promising tools for drug development. Based on this, in this study, we design...
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2024-09-01
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| author | Vasiliki Moulasioti Evgenia Fotou Vassilios Moussis Vassilios Tsikaris |
| author_facet | Vasiliki Moulasioti Evgenia Fotou Vassilios Moussis Vassilios Tsikaris |
| author_sort | Vasiliki Moulasioti |
| collection | DOAJ |
| description | Chemoselective reactions have played a crucial role in the development of high-molecular-weight (>3000 Da) macromolecules with a branched architecture, particularly as peptides and epitope-based vaccines have emerged as promising tools for drug development. Based on this, in this study, we designed and synthesized the peptide macromolecule <i>CH<sub>3</sub>CO</i>-[K-Aib-C(3,9-<i>CH<sub>2</sub>NHCOCH<sub>3</sub></i>; 6,12-DFLC(<i>CH<sub>2</sub>NHCOCH<sub>3</sub></i>)KKESEK)]<sub>4</sub>-NH<sub>2</sub> [<i>Ac</i>-K-Aib-C(3,9-<i>Acm</i>); 6,12-epitope)]<sub>4</sub>-<i>NH<sub>2</sub></i>] using chemoselective thioether bond formation between the peptide carrier CPSOC (3,9 Acm) and the <i>IAc</i>-DFLC<sub>(Acm)</sub>KKESEK-<i>NH<sub>2</sub></i> peptide epitope. The conjugate was purified via RP-HPLC and characterized via HR-ESI-MS. The epitope D<sup>128</sup>FLCKKESEK<sup>137</sup> derives from the lethal toxin, ammodytoxin A, from the V. ammodytes snake species, and it was synthesized using the SPPS Fmoc/tBu methodology and characterized via HR-ESI-MS and NMR techniques. |
| format | Article |
| id | doaj-art-fe9f72c449724a40bc6c1627fd73748d |
| institution | OA Journals |
| issn | 1422-8599 |
| language | English |
| publishDate | 2024-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj-art-fe9f72c449724a40bc6c1627fd73748d2025-08-20T02:01:10ZengMDPI AGMolbank1422-85992024-09-0120244M188710.3390/M1887<i>Ac</i>-[K-Aib-C(3,9-<i>Acm</i>; 6,12-DFLC<sub>(</sub><i><sub>Acm</sub></i><sub>)</sub>KKESEK)]<sub>4</sub>-<i>NH</i><sub>2</sub>Vasiliki Moulasioti0Evgenia Fotou1Vassilios Moussis2Vassilios Tsikaris3Sector of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, GreeceSector of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, GreeceSector of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, GreeceSector of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, GreeceChemoselective reactions have played a crucial role in the development of high-molecular-weight (>3000 Da) macromolecules with a branched architecture, particularly as peptides and epitope-based vaccines have emerged as promising tools for drug development. Based on this, in this study, we designed and synthesized the peptide macromolecule <i>CH<sub>3</sub>CO</i>-[K-Aib-C(3,9-<i>CH<sub>2</sub>NHCOCH<sub>3</sub></i>; 6,12-DFLC(<i>CH<sub>2</sub>NHCOCH<sub>3</sub></i>)KKESEK)]<sub>4</sub>-NH<sub>2</sub> [<i>Ac</i>-K-Aib-C(3,9-<i>Acm</i>); 6,12-epitope)]<sub>4</sub>-<i>NH<sub>2</sub></i>] using chemoselective thioether bond formation between the peptide carrier CPSOC (3,9 Acm) and the <i>IAc</i>-DFLC<sub>(Acm)</sub>KKESEK-<i>NH<sub>2</sub></i> peptide epitope. The conjugate was purified via RP-HPLC and characterized via HR-ESI-MS. The epitope D<sup>128</sup>FLCKKESEK<sup>137</sup> derives from the lethal toxin, ammodytoxin A, from the V. ammodytes snake species, and it was synthesized using the SPPS Fmoc/tBu methodology and characterized via HR-ESI-MS and NMR techniques.https://www.mdpi.com/1422-8599/2024/4/M1887CPSOC (3,9 Acm)peptide synthesischemoselective reactionpeptide macromoleculebranched architecture |
| spellingShingle | Vasiliki Moulasioti Evgenia Fotou Vassilios Moussis Vassilios Tsikaris <i>Ac</i>-[K-Aib-C(3,9-<i>Acm</i>; 6,12-DFLC<sub>(</sub><i><sub>Acm</sub></i><sub>)</sub>KKESEK)]<sub>4</sub>-<i>NH</i><sub>2</sub> Molbank CPSOC (3,9 Acm) peptide synthesis chemoselective reaction peptide macromolecule branched architecture |
| title | <i>Ac</i>-[K-Aib-C(3,9-<i>Acm</i>; 6,12-DFLC<sub>(</sub><i><sub>Acm</sub></i><sub>)</sub>KKESEK)]<sub>4</sub>-<i>NH</i><sub>2</sub> |
| title_full | <i>Ac</i>-[K-Aib-C(3,9-<i>Acm</i>; 6,12-DFLC<sub>(</sub><i><sub>Acm</sub></i><sub>)</sub>KKESEK)]<sub>4</sub>-<i>NH</i><sub>2</sub> |
| title_fullStr | <i>Ac</i>-[K-Aib-C(3,9-<i>Acm</i>; 6,12-DFLC<sub>(</sub><i><sub>Acm</sub></i><sub>)</sub>KKESEK)]<sub>4</sub>-<i>NH</i><sub>2</sub> |
| title_full_unstemmed | <i>Ac</i>-[K-Aib-C(3,9-<i>Acm</i>; 6,12-DFLC<sub>(</sub><i><sub>Acm</sub></i><sub>)</sub>KKESEK)]<sub>4</sub>-<i>NH</i><sub>2</sub> |
| title_short | <i>Ac</i>-[K-Aib-C(3,9-<i>Acm</i>; 6,12-DFLC<sub>(</sub><i><sub>Acm</sub></i><sub>)</sub>KKESEK)]<sub>4</sub>-<i>NH</i><sub>2</sub> |
| title_sort | i ac i k aib c 3 9 i acm i 6 12 dflc sub sub i sub acm sub i sub sub kkesek sub 4 sub i nh i sub 2 sub |
| topic | CPSOC (3,9 Acm) peptide synthesis chemoselective reaction peptide macromolecule branched architecture |
| url | https://www.mdpi.com/1422-8599/2024/4/M1887 |
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