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Improved solid-phase synthesis and study of arylopeptoids with conformation-directing side chains

Improved solid-phase synthesis and study of arylopeptoids with conformation-directing side chains

Hjelmgaard, Thomas, Faure, Sophie, De Santis, Emiliana, Staerk, Dan, Alexander, Bruce D., Edwards, Alison A., Taillefumier, Claude and Nielsen, John (2011) Improved solid-phase synthesis and study of arylopeptoids with conformation-directing side chains. Tetrahedron, 68 (23). pp. 4444-4454. ISSN 0040-4020 (doi:10.1016/j.tet.2011.12.049)

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Abstract

The development of an improved methodology for iterative solid-phase synthesis of para- and meta-arylopeptoids (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 allow for complete control over the amide conformation: the tert-butyl results in a 100% cis amide conformation while the phenyl side chain result in a 100% trans amide conformation. The method has furthermore enabled the first synthesis and study of arylopeptoids bearing (S)-N-(1-phenylethyl) side chains by means of circular dichroism.

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
Faculty / Department / Research Group: Faculty of Engineering & Science > Medway School of Pharmacy
Faculty of Engineering & Science > Department of Pharmaceutical, Chemical & Environmental Sciences
Related URLs:
Last Modified: 17 Oct 2016 09:11
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
URI: http://gala.gre.ac.uk/id/eprint/7265

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