An octameric carbopeptoid; secondary structure in octameric and tetrameric 5-aminomethyl-tetrahydrofuran-2-carboxylates

The efficient synthesis of an octameric furanose carbopeptoid, readily purified by chromatography in ethyl acetate:hexane (2:1), is reported. Extensive NMR studies suggest that two tetrameric 5-aminomethyltetrahydrofuran-2-carboxylates are prone to adopt solution conformations reminiscent of a repea...

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Bibliographic Details
Published in:Tetrahedron letters 1999-03, Vol.40 (11), p.2199-2202
Main Authors: Claridge, Timothy D.W., Long, Daniel D., Hungerford, Natasha L., Aplin, Robin T., Smith, Martin D., Marquess, Daniel G., Fleet, George W.J.
Format: Article
Language:English
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Summary:The efficient synthesis of an octameric furanose carbopeptoid, readily purified by chromatography in ethyl acetate:hexane (2:1), is reported. Extensive NMR studies suggest that two tetrameric 5-aminomethyltetrahydrofuran-2-carboxylates are prone to adopt solution conformations reminiscent of a repeating β-turn, a third tetramer and the corresponding octamer may tend towards a left-handed α-helix. The synthesis of an octameric carbopeptoid is described. 1H NMR studies provide preliminary evidence that the octamer and the tetramer may adopt a helical solution conformation in CDCl 3. Two stereoisomers of the tetramer may be predisposed to adopt a β-turn like secondary structure.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)00111-2