An unsaturated peptidomimetic assembly derived from a carbohydrate.
A strategy has been established for the synthesis of peptidomimetics derived from unsaturated carbohydrates, and exemplified by the use of methyl 2,6-anhydro-7-azido-3,7-deoxy-4,5-O-isopropylidene-D-lyxo-hept-2-enonate 9 as a dipeptide 'monomer' which can be elaborated from either end. Sel...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2004
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| _version_ | 1797086264615239680 |
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| author | Chung, Y Claridge, T Fleet, G Johnson, S Jones, J Lumbard, K Stachulski, A |
| author_facet | Chung, Y Claridge, T Fleet, G Johnson, S Jones, J Lumbard, K Stachulski, A |
| author_sort | Chung, Y |
| collection | OXFORD |
| description | A strategy has been established for the synthesis of peptidomimetics derived from unsaturated carbohydrates, and exemplified by the use of methyl 2,6-anhydro-7-azido-3,7-deoxy-4,5-O-isopropylidene-D-lyxo-hept-2-enonate 9 as a dipeptide 'monomer' which can be elaborated from either end. Selective reduction of 9 gives a protected pseudodipeptide ester suitable for use as an amino component, and saponification gives an azido acid suitable for use as a carboxyl component. The 'dimer' product of coupling these two components with TBTU can be similarly elaborated at either end to give a 'trimer' and a further cycle of selective reduction and coupling gave a 'tetramer', 17, a pseudo-octapeptide. |
| first_indexed | 2024-03-07T02:19:38Z |
| format | Journal article |
| id | oxford-uuid:a376cbaa-191f-4e5f-89da-c57c9f00f2fa |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T02:19:38Z |
| publishDate | 2004 |
| record_format | dspace |
| spelling | oxford-uuid:a376cbaa-191f-4e5f-89da-c57c9f00f2fa2022-03-27T02:27:15ZAn unsaturated peptidomimetic assembly derived from a carbohydrate.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:a376cbaa-191f-4e5f-89da-c57c9f00f2faEnglishSymplectic Elements at Oxford2004Chung, YClaridge, TFleet, GJohnson, SJones, JLumbard, KStachulski, AA strategy has been established for the synthesis of peptidomimetics derived from unsaturated carbohydrates, and exemplified by the use of methyl 2,6-anhydro-7-azido-3,7-deoxy-4,5-O-isopropylidene-D-lyxo-hept-2-enonate 9 as a dipeptide 'monomer' which can be elaborated from either end. Selective reduction of 9 gives a protected pseudodipeptide ester suitable for use as an amino component, and saponification gives an azido acid suitable for use as a carboxyl component. The 'dimer' product of coupling these two components with TBTU can be similarly elaborated at either end to give a 'trimer' and a further cycle of selective reduction and coupling gave a 'tetramer', 17, a pseudo-octapeptide. |
| spellingShingle | Chung, Y Claridge, T Fleet, G Johnson, S Jones, J Lumbard, K Stachulski, A An unsaturated peptidomimetic assembly derived from a carbohydrate. |
| title | An unsaturated peptidomimetic assembly derived from a carbohydrate. |
| title_full | An unsaturated peptidomimetic assembly derived from a carbohydrate. |
| title_fullStr | An unsaturated peptidomimetic assembly derived from a carbohydrate. |
| title_full_unstemmed | An unsaturated peptidomimetic assembly derived from a carbohydrate. |
| title_short | An unsaturated peptidomimetic assembly derived from a carbohydrate. |
| title_sort | unsaturated peptidomimetic assembly derived from a carbohydrate |
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