Recueil des Travaux Chimiques des Pays-Bas p. 278 - 286 (1993)
Update date:2022-08-02
Topics:
Hulsbergen, F. B.
Reedijk, J.
Five small, completely protected, L-histidyl(NτBzl)-containing peptides, were synthesized and characterized by NMR spectroscopy, i.e., R-Ala-His(Nτ-Bzl)-Ala-R' (1), R-His(Nτ-Bzl)-Ala-Ala-Ala-Met-R' (2), R-His(Nτ-Bzl)-Ala-Ala-Ala-His(Nτ-Bzl)-R' (3), R-His(Nτ-Bzl)-Ala-His(Nτ-Bzl)-Ala-His(Nτ-Bzl)-R' (4), R-His(Nτ-Bzl)-Ala-His(Nτ-Bzl)-R' (5), in which: R is phenylacetyl (PhCH2CO-, R' is phenylamino (-NHPh); Bzl is benzyl (PhCH2-).It has been shown that benzylation of histidine residues takes place at the Nτ atom of the imidazole.The resulting peptide derivatives appear to be good ligands for CoII, ZnII and CuI.Titrations of zinc chloride solutions towards peptide solutions (in dmso-d6, dimethyl sulfoxide followed by NMR spectroscopy show the formation of the two species
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(1993)Doi:10.1081/NCN-200059338
(2005)Doi:10.1248/cpb.26.3807
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(1993)