The synthesis of an EDTA-like chelating peptidomimetic building block suitable for solid-phase peptide synthesis. Issue 17 (15th February 2017)

• Record Type: Journal Article
• Authors: Spengler, Jan; Barker, Michael; Schelhorn, Constanze; García, Jesús; Macias, Maria J.; Albericio, Fernando
• Is Part Of: Chemical communications. Volume 53:Issue 17(2017)
• Page Start: 2634
• Page End: 2636
• Publication Date: 2017-02-15
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c6cc10203d
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A novo trifunctional EDTA-like peptidomimetic amino acid is described. Abstract : A novo trifunctional EDTA-like peptidomimetic amino acid is described. This unique building block, which is prepared in a straightforward manner from commercialized starting materials, contains three moieties: a hexadentate chelating unit similar to that present in EDTA, and amino and carboxylic groups, which facilitate its introduction into the backbone of peptides using conventional SPPS. As a proof of concept, this building block is introduced into a cyclic peptide inspired from the family of Gratisin analogues. The designed peptide contains the amino acid analogue in one of the turns, and chelates Ca 2+ with nanomolar affinity at physiological pH.