Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold
A novel convergent synthetic strategy for the construction of multicomponent self-adjuvanting lipopeptide vaccines was developed. A tetraalkyne-functionalized glucose derivative and lipidated Fmoc-lysine were prepared by novel efficient and convenient syntheses. The carbohydrate building block was c...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2014-07-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.181 |
| _version_ | 1818447543646814208 |
|---|---|
| author | Vincent Fagan Istvan Toth Pavla Simerska |
| author_facet | Vincent Fagan Istvan Toth Pavla Simerska |
| author_sort | Vincent Fagan |
| collection | DOAJ |
| description | A novel convergent synthetic strategy for the construction of multicomponent self-adjuvanting lipopeptide vaccines was developed. A tetraalkyne-functionalized glucose derivative and lipidated Fmoc-lysine were prepared by novel efficient and convenient syntheses. The carbohydrate building block was coupled to the self-adjuvanting lipidic moiety (three lipidated Fmoc-lysines) on solid support. Four copies of a group A streptococcal B cell epitope (J8) were then conjugated to the glyco-lipopeptide using a copper-catalyzed cycloaddition reaction. The approach was elaborated by the preparation of a second vaccine candidate which incorporated an additional promiscuous T-helper epitope. |
| first_indexed | 2024-12-14T20:05:18Z |
| format | Article |
| id | doaj.art-03a734163c6e47d3991ecdd6bbd31511 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T20:05:18Z |
| publishDate | 2014-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-03a734163c6e47d3991ecdd6bbd315112022-12-21T22:49:02ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-07-011011741174810.3762/bjoc.10.1811860-5397-10-181Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffoldVincent Fagan0Istvan Toth1Pavla Simerska2The University of Queensland, School of Chemistry and Molecular Biosciences, Cooper Road, St. Lucia QLD 4072, AustraliaThe University of Queensland, School of Chemistry and Molecular Biosciences, Cooper Road, St. Lucia QLD 4072, AustraliaThe University of Queensland, School of Chemistry and Molecular Biosciences, Cooper Road, St. Lucia QLD 4072, AustraliaA novel convergent synthetic strategy for the construction of multicomponent self-adjuvanting lipopeptide vaccines was developed. A tetraalkyne-functionalized glucose derivative and lipidated Fmoc-lysine were prepared by novel efficient and convenient syntheses. The carbohydrate building block was coupled to the self-adjuvanting lipidic moiety (three lipidated Fmoc-lysines) on solid support. Four copies of a group A streptococcal B cell epitope (J8) were then conjugated to the glyco-lipopeptide using a copper-catalyzed cycloaddition reaction. The approach was elaborated by the preparation of a second vaccine candidate which incorporated an additional promiscuous T-helper epitope.https://doi.org/10.3762/bjoc.10.181amino acid lipidationcycloadditon reactionmultivalent glycosystemspeptide vaccinetetrapropargyl glucopyranose |
| spellingShingle | Vincent Fagan Istvan Toth Pavla Simerska Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold Beilstein Journal of Organic Chemistry amino acid lipidation cycloadditon reaction multivalent glycosystems peptide vaccine tetrapropargyl glucopyranose |
| title | Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold |
| title_full | Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold |
| title_fullStr | Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold |
| title_full_unstemmed | Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold |
| title_short | Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold |
| title_sort | convergent synthetic methodology for the construction of self adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold |
| topic | amino acid lipidation cycloadditon reaction multivalent glycosystems peptide vaccine tetrapropargyl glucopyranose |
| url | https://doi.org/10.3762/bjoc.10.181 |
| work_keys_str_mv | AT vincentfagan convergentsyntheticmethodologyfortheconstructionofselfadjuvantinglipopeptidevaccinesusinganovelcarbohydratescaffold AT istvantoth convergentsyntheticmethodologyfortheconstructionofselfadjuvantinglipopeptidevaccinesusinganovelcarbohydratescaffold AT pavlasimerska convergentsyntheticmethodologyfortheconstructionofselfadjuvantinglipopeptidevaccinesusinganovelcarbohydratescaffold |