Document Detail

Reaction of [Pt(Gly-Gly-N,N',O)I]- with the N-acetylated dipeptide L-methionyl-L-histidine: selective platination of the histidine side chain by intramolecular migration of the platinum(II) complex.
MedLine Citation:
PMID:  18400244     Owner:  NLM     Status:  MEDLINE    
The reaction of the monofunctional [Pt(Gly-Gly-N,N',O)I](-) complex, in which Gly-Gly is the dipeptide glycyl-glycine coordinated through two nitrogen and oxygen atoms, with the N-acetylated dipeptide L-methionyl-L-histidine (MeCOMet-His) studied by (1)H NMR spectroscopy. All reactions were carried out in 50mM phosphate buffer at pD 7.4 and at 25 degrees C. In the initial stage of the reaction, the platinum(II) complex forms the kinetically favored [Pt(Gly-Gly-N,N',O)(MeCOMet-His-S)](-) complex, with unidentate coordination of the MeCOMet-His dipeptide through the sulfur atom of the methionine residue. In the second stage of the reaction, complete intramolecular migration of the [Pt(Gly-Gly-N,N',O)] unit from the sulfur to the N3 nitrogen atom of imidazole was observed and a new platinum(II)-peptide complex, [Pt(Gly-Gly-N,N',O)(MeCOMet-His-N3)](-) was formed. In comparison with previous results obtained for the reaction of [Pt(dien)Cl](+) with different methionine- and histidine-containing peptides, this migration reaction was sufficiently fast and strongly selective to the N3 atom of the imidazole ring of the histidine side chain. This study is an important step in the development of new platinum(II) complexes for selective covalent modification of peptides and proteins.
Marija D Zivković; Snezana Rajković; Milos I Djuran
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-04-08
Journal Detail:
Title:  Bioorganic chemistry     Volume:  36     ISSN:  1090-2120     ISO Abbreviation:  Bioorg. Chem.     Publication Date:  2008 Jun 
Date Detail:
Created Date:  2008-05-19     Completed Date:  2008-07-16     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  1303703     Medline TA:  Bioorg Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  161-4     Citation Subset:  IM    
Department of Chemistry, Faculty of Science, University of Kragujevac, R. Domanovića 12, PO Box 60, 34000 Kragujevac, Serbia.
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MeSH Terms
Dipeptides / chemistry*
Magnetic Resonance Spectroscopy
Organoplatinum Compounds / chemistry*
Reg. No./Substance:
0/Dipeptides; 0/Organoplatinum Compounds; 0/Peptides; 0/Proteins; 71-00-1/Histidine

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