Solid-phase synthesis of metal-complex containing peptides

Metal Complexes of Biologically Important Ligands, CLXXVI.[1] Formation of Peptides within the Coordination Sphere of Metal Ions and of Classical and Organometallic Complexes and Some Aspects of Prebiotic Chemistry

“…Merrifield Solid‐Phase Synthesis for the preparation of conjugates with classical and organometallic complexes has been highly developed and this field was recently covered in excellent reviews 177,234,236,248. So only some other organometallic examples are given.…”

“…Mostly using Solid‐Phase Synthesis technique (SPPS) many strong classical ligands have been introduced into peptides to afford novel metal‐peptide bioconjugates which can find application in biochemistry and catalysis. As has been comprehensively reviewed by Heinze ,234 Metzler‐Nolte , [174–178,236] and by Dirscherl and König 248 e.g. the following ligands have been attached to peptides for coordination to metal ions: Schiff‐bases, diimines, histidine, lysine, ethylene‐diamine, bis(picolyl)amine, iminodiacetate, porphyrin, various other bi‐,tri‐ and tetradendate ligands, more recently mono‐ and diphosphines243,244 and carbenes 270–272 .…”

The Use of Solid‐Phase Synthesis Techniques for the Preparation of Peptide–Metal Complex Conjugates

“…Peptides with metal complexes in their side chains and peptide–metal complex conjugates have been used to enhance or control binding affinities and peptide conformations 81. To extend the scope of solid‐phase synthesis of peptide–metal complex conjugates, König et al82 reported their preparation from modified amino acids bearing metal complex ligands or metal complexes in their side chains.The IDA motif, known for its ability to bind imidazole residues and N‐terminal His, was chosen and converted into its copper complex as a SAAC. This modified amino acid 143 was incorporated into a peptide sequence by standard solid‐phase peptide synthesis (Scheme ).…”

Synthesis and Self‐Assembly of NCN‐Pincer Pd‐Complex‐Bound Norvalines

“…Later, one‐pot single‐step installation of the metal was accomplished using method B, in which metal ions (M) are directly attached onto a metal‐coordination site at the α‐side‐chain by taking advantage of the low coordination ability of natural functional groups12 such as π‐coordinatable aromatic groups including phenyl alanine, tyrosine, and tryptophan13, 14 and/or sulfur functional groups including methionine or cysteine 14m,n. 15 The well‐known single amino acid chelates (SAACs)4a can be also categorized as this type, and a variety of SAACs bearing strong chelating ligands have been reported, such as bipyridine,16, 17a, 18a terpyridine,17 phenanthroline,18 cyclic amine,19 polycarboxylic acid,19b bis(2‐picolyl)amine19b, 20 and its naphthyl analogue,20b porphyrin,21 and alkyne 22…”