title: The synthesis of an EDTA-like chelating peptidomimetic building block suitable for solid-phase peptide synthesis.
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.
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac, 10, Barcelona E-08028, Spain and CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Barcelona, E-08028, Spain and Universidad Regional Amazónica IKIAM, Kilómetro 7 Vía Muyuna, Tena, Napo, Ecuador. jan.spengler@ikiam.edu.ec.
authors.forename: Jan
authors.initials: J
authors.lastname: Spengler
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac, 10, Barcelona E-08028, Spain and Erasmus+ funding through the University of Glasgow, College of Science and Engineering, Faculty of Chemistry Joseph Black Building, Glasgow G12 8QQ, Scotland, UK.
authors.forename: Michael
authors.initials: M
authors.lastname: Barker
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac, 10, Barcelona E-08028, Spain.
authors.forename: Constanze
authors.initials: C
authors.lastname: Schelhorn
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac, 10, Barcelona E-08028, Spain.
authors.forename: Jesús
authors.initials: J
authors.lastname: García
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac, 10, Barcelona E-08028, Spain and ICREA, Passeig Lluís Companys 23, E-08010-Barcelona, Spain.
authors.forename: Maria J
authors.initials: MJ
authors.lastname: Macias
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac, 10, Barcelona E-08028, Spain and CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Barcelona, E-08028, Spain and Department of Organic Chemistry, University of Barcelona, 08028-Barcelona, Spain and School of Chemistry & Physics, University of KwaZulu-Natal, Durban 4001, South Africa. albericio@ukzn.ac.za.
authors.forename: Fernando
authors.identifier: http://orcid.org/0000-0002-8946-0462
authors.initials: F
authors.lastname: Albericio
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D002614:Chelating Agents / Q000138:chemical synthesis* / Q000737:chemistry; D004492:Edetic Acid / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D057786:Peptidomimetics / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000596:Amino Acids; D002614:Chelating Agents; D010455:Peptides; D057786:Peptidomimetics; D004492:Edetic Acid