CC BY-ND-NC 4.0 · Synthesis 2019; 51(01): 31-39
DOI: 10.1055/s-0037-1610202
paper
Copyright with the author

Syntheses of Cyanophycin Segments for Investigations of Cell-Penetration

Marcel Grogg
Laboratorium für Organische Chemie (LOC), Departement Chemie und Angewandte, Biowissenschaften (D-CHAB), ETH-Zürich, Hönggerberg HCI, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland   Email: seebach@org.chem.ethz.ch
,
Donald Hilvert
Laboratorium für Organische Chemie (LOC), Departement Chemie und Angewandte, Biowissenschaften (D-CHAB), ETH-Zürich, Hönggerberg HCI, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland   Email: seebach@org.chem.ethz.ch
,
Albert K. Beck
Laboratorium für Organische Chemie (LOC), Departement Chemie und Angewandte, Biowissenschaften (D-CHAB), ETH-Zürich, Hönggerberg HCI, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland   Email: seebach@org.chem.ethz.ch
,
Dieter Seebach*
Laboratorium für Organische Chemie (LOC), Departement Chemie und Angewandte, Biowissenschaften (D-CHAB), ETH-Zürich, Hönggerberg HCI, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland   Email: seebach@org.chem.ethz.ch
› Author Affiliations
Further Information

Publication History

Received: 15 June 2018

Accepted: 15 June 2018

Publication Date:
28 June 2018 (eFirst)

  

§ This author did all the experiments

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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