Cyclic metallopeptides, cyclo[Gly-L-Cys(terpyPtII)]nCln†

Abstract

An efficient strategy for the liquid-phase synthesis of cyclic metallopeptides, cyclo[Gly-l-Cys(terpyPt II )] n Cl n (n = 3, 4), has been developed, which could provide a powerful tool for arraying metal centers on cyclopeptide frameworks. † Experimental and spectral data for 1a,b, 2 and 3 are available from the RSC web site, see

Platinum complexes of terpyridine: Interaction and reactivity with biomolecules

“…22) [86]. Through rapid reaction with the cysteine thiols, [Pt(terpy)Cl] + promotes peptide cyclization and can also act as a protecting group by subsequently being removed through treatment with tetrafluoroacetic acid.…”

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

“…Other silver‐ion‐templated cyclizations of amino acids afforded natural products: Oxazole and thiazole based amino acids undergo cyclization in the presence of AgBF 4 ;53 the presence of AgBF 4 improved the cyclization of a linear hexadepsipeptide considerably 54. Linear cysteine containing peptides were coordinated to Pt II ( 8 ) and were cyclized to give cyclo‐[Gly‐Cyst(terpyridine)Pt] n n + metallopeptides 55. Cyclic tripeptoids have been obtained from a tripeptide with an aryl halide as side chain by Cu I or Pd 0 catalysis 56…”

16 The noble metals

“…263 The functionalisation of cyclopeptides using metal atoms was achieved by the synthesis of cyclo-[Gly-L-CysPt(terpy)] n Cl n (n 3 or 4), leading to possible interesting metal and organic chemistry. 264 Protonation of the 1-methyluracilate (L 19 ) complex trans-[Pt(L 19 ) 2 (NH 3 ) 2 ] to form trans-[Pt(HL 19 ) 2 (NH 3 ) 2 ] 2 gives greatly enhanced water solubility. This property is employed in reactions with metal salts to give trans-[{Pt(L 19 ) 2 (NH 3 ) 2 }Ag 3 ] 3 and trans-[{Pt(L 19 ) 2 (NH 3 ) 2 } 2 AgNa(H 2 O) 4 ] 2 ; the latter is claimed to be the ¢rst nucleobase complex of three different metal ions.…”