Johnson, Stephen W. and Jenkinson, Sarah F. and Perez-Victoria, Ignacio and Edwards, Alison A. and Claridge, Timothy D.W. and Tranter, George E. and Fleet, George W.J. and Jones, John J. (2004) Conformational studies of oligomeric oxetane-based dipeptide isosteres derived from L-rhamnose or D-xylose. Journal of Peptide Science, 11 (9). pp. 517-524. ISSN 1075-2617.
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Abstract
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.
| Item Type: | Article |
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| Subjects: | Q Science Q Science > QD Chemistry |
| Divisions: | Faculties > Science Technology and Medical Studies > Medway School of Pharmacy |
| Depositing User: | Alison Edwards |
| Date Deposited: | 08 Sep 2008 15:04 |
| Last Modified: | 17 Jul 2012 14:24 |
| Resource URI: | http://kar.kent.ac.uk/id/eprint/4891 (The current URI for this page, for reference purposes) |
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