Silver-promoted solid-phase guanidinylation enables the first synthesis of arginine glycosylated Samoamide A cyclopeptide analogue
Cyclization and glycosylation serve as effective approaches for enhancing the drug properties of peptides. Distinct from typical glycosylation, atypical arginine N-glycosylation has drawn increasing attention due to its fundamental role in various cellular procedures and signaling pathways. We previ...
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2023-01-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fchem.2022.1040216/full |
| _version_ | 1828071829443444736 |
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| author | Bingxin Liang Rong Li Linji Li Ming Tang Xiang Li Chunli Su Hongli Liao |
| author_facet | Bingxin Liang Rong Li Linji Li Ming Tang Xiang Li Chunli Su Hongli Liao |
| author_sort | Bingxin Liang |
| collection | DOAJ |
| description | Cyclization and glycosylation serve as effective approaches for enhancing the drug properties of peptides. Distinct from typical glycosylation, atypical arginine N-glycosylation has drawn increasing attention due to its fundamental role in various cellular procedures and signaling pathways. We previously developed a robust strategy for constructing arginine N-glycosylated peptides characterized by silver-promoted solid-phase guanidinylation. Modeled after cyclic octapeptide Samoamide A, an antitumor peptide composed of eight hydrophobic amino acids extracted from cyanobacteria, herein we first performed arginine scanning to determine an optimal position for replacement with arginine. Consequently, the first synthesis of arginine glycosylated Samoamide A cyclopeptide analogue was described combining solid-phase glycosylation with solution-phase cyclization. The resultant SA-HH-TT displayed enhanced water solubility compared with the non-glycosylated SA-HH-TT. Notably, our method provides a universal strategy for synthesizing arginine N-glycosylated cyclopeptides. |
| first_indexed | 2024-04-11T00:59:40Z |
| format | Article |
| id | doaj.art-4e696330d6f6434fb6a8ef67c439e855 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-04-11T00:59:40Z |
| publishDate | 2023-01-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-4e696330d6f6434fb6a8ef67c439e8552023-01-04T18:23:16ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462023-01-011010.3389/fchem.2022.10402161040216Silver-promoted solid-phase guanidinylation enables the first synthesis of arginine glycosylated Samoamide A cyclopeptide analogueBingxin Liang0Rong Li1Linji Li2Ming Tang3Xiang Li4Chunli Su5Hongli Liao6School of Pharmacy, Chengdu Medical College, Chengdu, ChinaSchool of Pharmacy, Chengdu Medical College, Chengdu, ChinaSchool of Pharmacy, Chengdu Medical College, Chengdu, ChinaSchool of Pharmacy, Chengdu Medical College, Chengdu, ChinaSchool of Pharmacy, Second Military Medical University, Shanghai, ChinaSchool of Public Health, Chengdu Medical College, Chengdu, ChinaSchool of Pharmacy, Chengdu Medical College, Chengdu, ChinaCyclization and glycosylation serve as effective approaches for enhancing the drug properties of peptides. Distinct from typical glycosylation, atypical arginine N-glycosylation has drawn increasing attention due to its fundamental role in various cellular procedures and signaling pathways. We previously developed a robust strategy for constructing arginine N-glycosylated peptides characterized by silver-promoted solid-phase guanidinylation. Modeled after cyclic octapeptide Samoamide A, an antitumor peptide composed of eight hydrophobic amino acids extracted from cyanobacteria, herein we first performed arginine scanning to determine an optimal position for replacement with arginine. Consequently, the first synthesis of arginine glycosylated Samoamide A cyclopeptide analogue was described combining solid-phase glycosylation with solution-phase cyclization. The resultant SA-HH-TT displayed enhanced water solubility compared with the non-glycosylated SA-HH-TT. Notably, our method provides a universal strategy for synthesizing arginine N-glycosylated cyclopeptides.https://www.frontiersin.org/articles/10.3389/fchem.2022.1040216/fullcyclopeptide synthesisarginine N-glycosylationsolid-phase glycosylationSamoamide Aantitumor biological activity |
| spellingShingle | Bingxin Liang Rong Li Linji Li Ming Tang Xiang Li Chunli Su Hongli Liao Silver-promoted solid-phase guanidinylation enables the first synthesis of arginine glycosylated Samoamide A cyclopeptide analogue Frontiers in Chemistry cyclopeptide synthesis arginine N-glycosylation solid-phase glycosylation Samoamide A antitumor biological activity |
| title | Silver-promoted solid-phase guanidinylation enables the first synthesis of arginine glycosylated Samoamide A cyclopeptide analogue |
| title_full | Silver-promoted solid-phase guanidinylation enables the first synthesis of arginine glycosylated Samoamide A cyclopeptide analogue |
| title_fullStr | Silver-promoted solid-phase guanidinylation enables the first synthesis of arginine glycosylated Samoamide A cyclopeptide analogue |
| title_full_unstemmed | Silver-promoted solid-phase guanidinylation enables the first synthesis of arginine glycosylated Samoamide A cyclopeptide analogue |
| title_short | Silver-promoted solid-phase guanidinylation enables the first synthesis of arginine glycosylated Samoamide A cyclopeptide analogue |
| title_sort | silver promoted solid phase guanidinylation enables the first synthesis of arginine glycosylated samoamide a cyclopeptide analogue |
| topic | cyclopeptide synthesis arginine N-glycosylation solid-phase glycosylation Samoamide A antitumor biological activity |
| url | https://www.frontiersin.org/articles/10.3389/fchem.2022.1040216/full |
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