Syntheses of Cyanophycin Segments for Investigations of Cell-Penetration
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Date
2019-01
Publication Type
Journal Article
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yes
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Abstract
Novel guanidinium-rich oligopeptide derivatives R-[Adp(X)]8-NH2 are described, which consist of an octa-aspartic acid backbone with argininylated side chains that are derived from the biopolymer cyanophycin [H-(Adp)n-OH]. The Fmoc-Adp(X,Pbf)-OH building blocks for solid-state peptide synthesis (SSPS) of Adp octamers were prepared from Fmoc-Arg(Pbf)-OH and Fmoc-Asp-OAll. Coupling on PAL resin provided four octamers with and without N-terminal fluorescent groups (FAM) and C-terminal amide groups. Milligram quantities of Adp-octamers were isolated after preparative HPLC purification. The structure of the novel guanidinium-rich oligomers is unique insofar as the side chains of the Asp8-backbone include both a guanidino and a carboxylic acid group, the influence of which will be tested with the corresponding ester and amide derivatives that were synthesized in parallel. Unusual cell-penetrating properties of the Adp-octamers are expected.
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published
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Journal / series
Volume
51 (1)
Pages / Article No.
31 - 39
Publisher
Thieme
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Subject
guanidinium-rich oligopeptides; β3/α-Asp-Arg-dipeptide building block; biopolymer cyanophycin; solid-state peptide synthesis; cell-penetrating peptides
Organisational unit
03492 - Hilvert, Donald (emeritus) / Hilvert, Donald (emeritus)