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Open Access A Journey from the Pool of Chiral Synthetic Building Blocks to Cell-Penetrating Peptides, to a Novel Type of Enzyme – and back

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The roles of polyhydroxy-butyrates/alkanoates (PHB/PHA) in biology, for the preparation of chiral building blocks, and as a source of inspiration for the discovery of β- and γ-peptides are discussed. The syntheses and structures of β-peptides are outlined. The prerequisites for mimicking peptide/protein interactions with β-peptides and two examples are presented. Single terminal β-amino-acid residues can lead to stabilization of peptides (cf. NTS(8-13)) in plasma. Cell-penetrating α-L-, α-D-, mixed α-L/D- and β-oligoarginines (OAs) and -oligoprolines, as well as the mechanism(s) of internalization are compared. Recent studies show that infected erythrocytes, parasitic organisms and mycobacteria are entered by OA-derivatives, which have been employed as transporters of the antibiotic fosmidomycin. While β-peptides are generally enzymatically stable (for days in mammals), a microorganism (S. xenopeptidilytica) with an Ntn enzyme (3-2W4 BapA) was discovered that cleaves only β-peptides, and that was applied in preparations of (enantiopure) β-amino acids and β-peptides.

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Keywords: BETA-PEPTIDES; CELL-PENETRATING PEPTIDES; FOSMIDOMYCIN; OLIGOARGININES; PEPTIDOMIMETICS; POLYHYDROXYBUTYRATE; TERMINAL HOMOLOGATION OF PEPTIDES

Document Type: Research Article

Affiliations: Laboratorium für Organische Chemie der ETH Zürich, Wolfgang-Pauli-Strasse 10, CH-8093 Zürich, Switzerland

Publication date: December 1, 2013

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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