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. 2022 Jun 8:99:153848.
doi: 10.1016/j.tetlet.2022.153848. Epub 2022 May 6.

Canavanine versus arginine: Prospects for cell-penetrating peptides

Lindsey O Calabretta  1 , Vienna M Thomas  2 , Ronald T Raines  1
Affiliations

Canavanine versus arginine: Prospects for cell-penetrating peptides

Lindsey O Calabretta et al. Tetrahedron Lett. .

Abstract

Octanol-water partitioning experiments in the presence of carboxylate-, phosphate-, and sulfate-containing anionic lipids revealed that Ac-Cav-NH2 (where Cav refers to δ-oxa-arginine) partitions less into octanol than does Ac-Arg-NH2, suggesting that a cell-penetrating peptide based on canavanine would be relatively ineffective.

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Figures

Figure 1.
Figure 1.
Graph showing the octanol–water partitioning of 1·HCl and 2·HCl in the presence of anionic lipids 6, 7, or 8 (2.5 equiv) at pH 7.4 (unless indicated otherwise). Values were determined by 1H-NMR spectroscopy in duplicate experiments (Figures S2–S4).
Scheme 1.
Scheme 1.
Structures of Ac-Arg-NH2·HCl (1·HCl) and Ac-Cav-NH2·HCl (2·HCl).
Scheme 2.
Scheme 2.
Synthetic route to Ac-Cav-NH2·HCl (2·HCl).
See this image and copyright information in PMC

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