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Issue 17, 2017
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The synthesis of an EDTA-like chelating peptidomimetic building block suitable for solid-phase peptide synthesis

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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 Ca2+ with nanomolar affinity at physiological pH.

Graphical abstract: The synthesis of an EDTA-like chelating peptidomimetic building block suitable for solid-phase peptide synthesis

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Article information


Submitted
23 Dec 2016
Accepted
31 Jan 2017
First published
03 Feb 2017

Chem. Commun., 2017,53, 2634-2636
Article type
Communication

The synthesis of an EDTA-like chelating peptidomimetic building block suitable for solid-phase peptide synthesis

J. Spengler, M. Barker, C. Schelhorn, J. García, M. J. Macias and F. Albericio, Chem. Commun., 2017, 53, 2634
DOI: 10.1039/C6CC10203D

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