Improved solid-phase synthesis and study of arylopeptoids with conformation-directing side chains
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Hjelmgaard, Thomas, Faure, Sophie, De Santis, Emiliana, Staerk, Dan, Alexander, Bruce D., Edwards, Alison A., Taillefumier, Claude and Nielsen, John (2012) Improved solid-phase synthesis and study of arylopeptoids with conformation-directing side chains. Tetrahedron, 68 (23). pp. 4444-4454. ISSN 0040-4020
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Abstract
The development of an improved methodology for iterative solid-phase synthesis of para- and metaarylopeptoids
(oligomeric N-substituted aminomethyl benzamides) using benzoyl chloride building blocks is described. This methodology has enabled the synthesis of arylopeptoids with tert-butyl and phenyl side chains, which allows for complete control over the amide conformation: the tert-butyl results in a 100% cis amide conformation while the phenyl side chain results in a 100% trans amide conformation. The method has furthermore enabled the first synthesis and preliminary conformational studies of arylopeptoids bearing (S)-N-(1-phenylethyl) side chains.
| Item Type: | Article |
|---|---|
| Additional Information: | [1] Methods used for analytical and preparative HPLC; HPLC profiles and NMR spectra of all synthesized arylopeptoids; NOESY spectra of p/m-4b and p/m-4c; temperature NMR studies of p/m-4a; CD spectra of arylopeptoids with spe side chains in CDCl3. Supplementary data associated with this article can be found, in the online version, at doi:10.1016/j.tet.2011.12.049. |
| Uncontrolled Keywords: | foldamers, aromatic oligoamides, peptoids, solid-phase synthesis, conformational analysis |
| Subjects: | Q Science > QD Chemistry |
| School / Department / Research Groups: | School of Science School of Science > Department of Pharmaceutical, Chemical & Environmental Sciences |
| Related URLs: | |
| Last Modified: | 14 Jun 2012 10:57 |
| URI: | http://gala.gre.ac.uk/id/eprint/8370 |
Available Versions of this Item
- Improved solid-phase synthesis and study of arylopeptoids with conformation-directing side chains. (deposited 13 Jan 2012 17:29)
- Improved solid-phase synthesis and study of arylopeptoids with conformation-directing side chains. (deposited 14 Jun 2012 10:56)[Currently Displayed]
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