Spirodiketopiperazines of mannofuranose: carbopeptoid alpha-amino acid esters at the anomeric position of mannofuranose
Epimeric mannofuranose anomeric aminoesters are prepared from readily available azidolactones and can act as building blocks for the incorporation of mannofuranose units into peptide chains [carbopeptoids]; alternative acylating conditions allow either rapid acylation of the more stable but kinetica...
| Main Authors: | , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
1998
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| _version_ | 1797093687781490688 |
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| author | Estevez, J Burton, J Estevez, R Ardron, H Wormald, MR Dwek, R Brown, D Fleet, G |
| author_facet | Estevez, J Burton, J Estevez, R Ardron, H Wormald, MR Dwek, R Brown, D Fleet, G |
| author_sort | Estevez, J |
| collection | OXFORD |
| description | Epimeric mannofuranose anomeric aminoesters are prepared from readily available azidolactones and can act as building blocks for the incorporation of mannofuranose units into peptide chains [carbopeptoids]; alternative acylating conditions allow either rapid acylation of the more stable but kinetically hindered amine or reaction with the less hindered but less stable amine to allow control of the anomeric configuration of the products. This is exemplified by coupling of the aminoesters with glycine derivatives to give dipeptide equivalents, and subsequent cyclization to spiro diketopiperazines. Anomers with the nitrogen function cis to the 2,3-diol are more stable than those with nitrogen trans; mannofuranose derivatives are more Stable than the mannopyranose isomers. |
| first_indexed | 2024-03-07T04:03:54Z |
| format | Journal article |
| id | oxford-uuid:c581956d-2909-469d-8e26-cbb8654dd198 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:03:54Z |
| publishDate | 1998 |
| record_format | dspace |
| spelling | oxford-uuid:c581956d-2909-469d-8e26-cbb8654dd1982022-03-27T06:31:27ZSpirodiketopiperazines of mannofuranose: carbopeptoid alpha-amino acid esters at the anomeric position of mannofuranoseJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:c581956d-2909-469d-8e26-cbb8654dd198EnglishSymplectic Elements at Oxford1998Estevez, JBurton, JEstevez, RArdron, HWormald, MRDwek, RBrown, DFleet, GEpimeric mannofuranose anomeric aminoesters are prepared from readily available azidolactones and can act as building blocks for the incorporation of mannofuranose units into peptide chains [carbopeptoids]; alternative acylating conditions allow either rapid acylation of the more stable but kinetically hindered amine or reaction with the less hindered but less stable amine to allow control of the anomeric configuration of the products. This is exemplified by coupling of the aminoesters with glycine derivatives to give dipeptide equivalents, and subsequent cyclization to spiro diketopiperazines. Anomers with the nitrogen function cis to the 2,3-diol are more stable than those with nitrogen trans; mannofuranose derivatives are more Stable than the mannopyranose isomers. |
| spellingShingle | Estevez, J Burton, J Estevez, R Ardron, H Wormald, MR Dwek, R Brown, D Fleet, G Spirodiketopiperazines of mannofuranose: carbopeptoid alpha-amino acid esters at the anomeric position of mannofuranose |
| title | Spirodiketopiperazines of mannofuranose: carbopeptoid alpha-amino acid esters at the anomeric position of mannofuranose |
| title_full | Spirodiketopiperazines of mannofuranose: carbopeptoid alpha-amino acid esters at the anomeric position of mannofuranose |
| title_fullStr | Spirodiketopiperazines of mannofuranose: carbopeptoid alpha-amino acid esters at the anomeric position of mannofuranose |
| title_full_unstemmed | Spirodiketopiperazines of mannofuranose: carbopeptoid alpha-amino acid esters at the anomeric position of mannofuranose |
| title_short | Spirodiketopiperazines of mannofuranose: carbopeptoid alpha-amino acid esters at the anomeric position of mannofuranose |
| title_sort | spirodiketopiperazines of mannofuranose carbopeptoid alpha amino acid esters at the anomeric position of mannofuranose |
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