Carbopeptoids: peptides and diketopiperazines incorporating the anomeric centre of mannopyranose
An approach to the synthesis of D-mannopyranose derivatives incorporating an anomeric α-amino acid component is described. An N-acylated bicyclic [2.2.2] lactone, formed via an oxidative ring closure, provides access to a new class of glycopeptide analogues of D-mannopyranose and determines the anom...
| Hauptverfasser: | , , , , , , |
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| Format: | Journal article |
| Sprache: | English |
| Veröffentlicht: |
2001
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| _version_ | 1826300268014206976 |
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| author | Long, D Tennant-Eyles, R Estevez, J Wormald, M Dwek, R Smith, M Fleet, G |
| author_facet | Long, D Tennant-Eyles, R Estevez, J Wormald, M Dwek, R Smith, M Fleet, G |
| author_sort | Long, D |
| collection | OXFORD |
| description | An approach to the synthesis of D-mannopyranose derivatives incorporating an anomeric α-amino acid component is described. An N-acylated bicyclic [2.2.2] lactone, formed via an oxidative ring closure, provides access to a new class of glycopeptide analogues of D-mannopyranose and determines the anomeric configuration of compounds derived therefrom. The mannopyranose diketopiperazine may be equilibrated to the more stable furanose form under basic conditions; in general, mannopyranose derivatives containing an α-amino acid moiety at the anomeric position are less stable than the mannofuranose isomers. |
| first_indexed | 2024-03-07T05:14:35Z |
| format | Journal article |
| id | oxford-uuid:dcbbcd7e-1a5d-42a6-9185-c0d6ad1af5af |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:14:35Z |
| publishDate | 2001 |
| record_format | dspace |
| spelling | oxford-uuid:dcbbcd7e-1a5d-42a6-9185-c0d6ad1af5af2022-03-27T09:19:42ZCarbopeptoids: peptides and diketopiperazines incorporating the anomeric centre of mannopyranoseJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:dcbbcd7e-1a5d-42a6-9185-c0d6ad1af5afEnglishSymplectic Elements at Oxford2001Long, DTennant-Eyles, REstevez, JWormald, MDwek, RSmith, MFleet, GAn approach to the synthesis of D-mannopyranose derivatives incorporating an anomeric α-amino acid component is described. An N-acylated bicyclic [2.2.2] lactone, formed via an oxidative ring closure, provides access to a new class of glycopeptide analogues of D-mannopyranose and determines the anomeric configuration of compounds derived therefrom. The mannopyranose diketopiperazine may be equilibrated to the more stable furanose form under basic conditions; in general, mannopyranose derivatives containing an α-amino acid moiety at the anomeric position are less stable than the mannofuranose isomers. |
| spellingShingle | Long, D Tennant-Eyles, R Estevez, J Wormald, M Dwek, R Smith, M Fleet, G Carbopeptoids: peptides and diketopiperazines incorporating the anomeric centre of mannopyranose |
| title | Carbopeptoids: peptides and diketopiperazines incorporating the anomeric centre of mannopyranose |
| title_full | Carbopeptoids: peptides and diketopiperazines incorporating the anomeric centre of mannopyranose |
| title_fullStr | Carbopeptoids: peptides and diketopiperazines incorporating the anomeric centre of mannopyranose |
| title_full_unstemmed | Carbopeptoids: peptides and diketopiperazines incorporating the anomeric centre of mannopyranose |
| title_short | Carbopeptoids: peptides and diketopiperazines incorporating the anomeric centre of mannopyranose |
| title_sort | carbopeptoids peptides and diketopiperazines incorporating the anomeric centre of mannopyranose |
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