Conformational studies of oligomeric oxetane-based dipeptide isosteres derived from L-rhamnose or D-xylose.
Conformational investigations have been undertaken on oligomers (dimers, tetramers, hexamers) of five closely related oxetane-based dipeptide isosteres. All the oligomers were subjected to a range of studies by NMR, FT-IR and CD spectroscopy. The oligomers derived from methyl 2,4-anhydro-5-azido-3-O...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Journal article |
| Language: | English |
| Published: |
2005
|
| _version_ | 1797076522453958656 |
|---|---|
| author | Johnson, S Jenkinson, S Pérez-Victoria, I Edwards, A Claridge, T Tranter, G Fleet, G Jones, J |
| author_facet | Johnson, S Jenkinson, S Pérez-Victoria, I Edwards, A Claridge, T Tranter, G Fleet, G Jones, J |
| author_sort | Johnson, S |
| collection | OXFORD |
| description | Conformational investigations have been undertaken on oligomers (dimers, tetramers, hexamers) of five closely related oxetane-based dipeptide isosteres. All the oligomers were subjected to a range of studies by NMR, FT-IR and CD spectroscopy. The oligomers derived from methyl 2,4-anhydro-5-azido-3-O-tert-butyldimethylsilyl-5-deoxy-L-rhamnonate 'monomer' all exhibited evidence of ordered conformations in chloroform and 2,2,2-trifluoroethanol (TFE) solution. 5-Acetamido and N-methylamide derivatives of the L-rhamnonate 'monomer', along with a 'dimer' lacking silyl protection at C-3, were synthesized to ascertain the role of intramolecular interactions. This led to the conclusion that, for the L-rhamnonate oligomers, steric interactions govern the conformational preference observed. The equivalent silyl-protected D-lyxonate oligomers gave ordered CD spectra in TFE solution, but NMR and FT-IR spectroscopy in chloroform solution suggested an irregular, non-hydrogen bonded system. The remaining silyl-protected 6-deoxy-L-altronate, 6-deoxy-D-gulonate and D-fuconate oligomers appear to be characterized by their lack of ordered conformation in TFE and chloroform solution. |
| first_indexed | 2024-03-07T00:04:54Z |
| format | Journal article |
| id | oxford-uuid:773a2c5a-5be7-4f24-b359-983d774b8e2a |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T00:04:54Z |
| publishDate | 2005 |
| record_format | dspace |
| spelling | oxford-uuid:773a2c5a-5be7-4f24-b359-983d774b8e2a2022-03-26T20:22:25ZConformational studies of oligomeric oxetane-based dipeptide isosteres derived from L-rhamnose or D-xylose.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:773a2c5a-5be7-4f24-b359-983d774b8e2aEnglishSymplectic Elements at Oxford2005Johnson, SJenkinson, SPérez-Victoria, IEdwards, AClaridge, TTranter, GFleet, GJones, JConformational investigations have been undertaken on oligomers (dimers, tetramers, hexamers) of five closely related oxetane-based dipeptide isosteres. All the oligomers were subjected to a range of studies by NMR, FT-IR and CD spectroscopy. The oligomers derived from methyl 2,4-anhydro-5-azido-3-O-tert-butyldimethylsilyl-5-deoxy-L-rhamnonate 'monomer' all exhibited evidence of ordered conformations in chloroform and 2,2,2-trifluoroethanol (TFE) solution. 5-Acetamido and N-methylamide derivatives of the L-rhamnonate 'monomer', along with a 'dimer' lacking silyl protection at C-3, were synthesized to ascertain the role of intramolecular interactions. This led to the conclusion that, for the L-rhamnonate oligomers, steric interactions govern the conformational preference observed. The equivalent silyl-protected D-lyxonate oligomers gave ordered CD spectra in TFE solution, but NMR and FT-IR spectroscopy in chloroform solution suggested an irregular, non-hydrogen bonded system. The remaining silyl-protected 6-deoxy-L-altronate, 6-deoxy-D-gulonate and D-fuconate oligomers appear to be characterized by their lack of ordered conformation in TFE and chloroform solution. |
| spellingShingle | Johnson, S Jenkinson, S Pérez-Victoria, I Edwards, A Claridge, T Tranter, G Fleet, G Jones, J Conformational studies of oligomeric oxetane-based dipeptide isosteres derived from L-rhamnose or D-xylose. |
| title | Conformational studies of oligomeric oxetane-based dipeptide isosteres derived from L-rhamnose or D-xylose. |
| title_full | Conformational studies of oligomeric oxetane-based dipeptide isosteres derived from L-rhamnose or D-xylose. |
| title_fullStr | Conformational studies of oligomeric oxetane-based dipeptide isosteres derived from L-rhamnose or D-xylose. |
| title_full_unstemmed | Conformational studies of oligomeric oxetane-based dipeptide isosteres derived from L-rhamnose or D-xylose. |
| title_short | Conformational studies of oligomeric oxetane-based dipeptide isosteres derived from L-rhamnose or D-xylose. |
| title_sort | conformational studies of oligomeric oxetane based dipeptide isosteres derived from l rhamnose or d xylose |
| work_keys_str_mv | AT johnsons conformationalstudiesofoligomericoxetanebaseddipeptideisosteresderivedfromlrhamnoseordxylose AT jenkinsons conformationalstudiesofoligomericoxetanebaseddipeptideisosteresderivedfromlrhamnoseordxylose AT perezvictoriai conformationalstudiesofoligomericoxetanebaseddipeptideisosteresderivedfromlrhamnoseordxylose AT edwardsa conformationalstudiesofoligomericoxetanebaseddipeptideisosteresderivedfromlrhamnoseordxylose AT claridget conformationalstudiesofoligomericoxetanebaseddipeptideisosteresderivedfromlrhamnoseordxylose AT tranterg conformationalstudiesofoligomericoxetanebaseddipeptideisosteresderivedfromlrhamnoseordxylose AT fleetg conformationalstudiesofoligomericoxetanebaseddipeptideisosteresderivedfromlrhamnoseordxylose AT jonesj conformationalstudiesofoligomericoxetanebaseddipeptideisosteresderivedfromlrhamnoseordxylose |