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Highly Constrained Linear Oligopeptides Containing Heterocyclic alpha-Amino Carboxylic Acids


Stoykova, Svetlana A; Linden, Anthony; Heimgartner, Heinz (2013). Highly Constrained Linear Oligopeptides Containing Heterocyclic alpha-Amino Carboxylic Acids. Helvetica Chimica Acta, 96(9):1714-1732.

Abstract

Two spiroheterocyclic 2H-azirin-3-amines, 1f and 1g, were shown to be useful synthons for the dipeptides N-(4-aminotetrahydro-2H-pyran-4-yl)prolinate (Thp-Pro) and the corresponding thiopyran derivative, Tht-Pro, respectively. By coupling of 4-bromobenzoic acid with 1f or 1g and saponification, followed by repeating the coupling and saponification steps, oligopeptides of type 4-BrBz-(Thp-Pro)n-OMe and 4-BrBz-(Tht-Pro)n-OMe were prepared, and their conformations were evaluated in solution by NMR techniques and in the crystalline state by X-ray crystallography. All of these sterically highly congested oligopeptides adopt fairly rigid helical conformations. It is interesting to note that the hexapeptide with Thp forms a 310-helix, whereas the Tht analog has a beta-bend ribbon spiral conformation.

Abstract

Two spiroheterocyclic 2H-azirin-3-amines, 1f and 1g, were shown to be useful synthons for the dipeptides N-(4-aminotetrahydro-2H-pyran-4-yl)prolinate (Thp-Pro) and the corresponding thiopyran derivative, Tht-Pro, respectively. By coupling of 4-bromobenzoic acid with 1f or 1g and saponification, followed by repeating the coupling and saponification steps, oligopeptides of type 4-BrBz-(Thp-Pro)n-OMe and 4-BrBz-(Tht-Pro)n-OMe were prepared, and their conformations were evaluated in solution by NMR techniques and in the crystalline state by X-ray crystallography. All of these sterically highly congested oligopeptides adopt fairly rigid helical conformations. It is interesting to note that the hexapeptide with Thp forms a 310-helix, whereas the Tht analog has a beta-bend ribbon spiral conformation.

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Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:September 2013
Deposited On:25 Sep 2013 12:49
Last Modified:05 Apr 2016 17:00
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.201300062
Official URL:http://onlinelibrary.wiley.com/doi/10.1002/hlca.201300062/abstract

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