New selectivity in peptide hydrolysis by metal complexes. Platinum(II) complexes promote cleavage of peptides next to the tryptophan residue

Inorganic Chemistry
N V Kaminskaia, N M Kostic

Abstract

Tryptophan-containing N-acetylated peptides AcTrp-Gly, AcTrp-Ala, AcTrp-Val, and AcTrp-ValOMe bind to platinum(II) and undergo selective hydrolytic cleavage of the C-terminal amide bond; the N-terminal amide bond remains intact. In acetone solution, bidentate coordination of the tryptophanyl residue via the C(3) atom of indole and the amide oxygen atom produces complexes of spiro stereochemistry, which are characterized by (1)H, (13)C, and (195)Pt NMR spectroscopy, and also by UV-vis, IR, and mass spectroscopy. Upon addition of 1 molar equiv of water, these complexes undergo hydrolytic cleavage. This reaction is as much as 10(4)-10(5) times faster in the presence of platinum(II) complexes than in their absence. The hydrolysis is conveniently monitored by (1)H NMR spectroscopy. We report the kinetics and mechanism for this reaction between cis-[Pt(en)(sol)(2)](2+), in which the solvent ligand is water or acetone, and AcTrp-Ala. The platinum(II) ion as a Lewis acid activates the oxygen-bound amide group toward nucleophilic attack of solvent water. The reaction is unimolecular with respect to the metal-peptide complex. Because the tryptophanyl fragment AcTrp remains coordinated to platinum(II) after cleavage of the amide bond, the...Continue Reading

References

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Oct 24, 2001·Inorganic Chemistry·Natalia V. Kaminskaia, Nenad M. Kostic

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Citations

Jul 31, 2013·Journal of Photochemistry and Photobiology. B, Biology·Benchawan JityutiApinya Buranaprapuk
Jun 30, 2015·MAbs·Zephania Kwong GloverAlavattam Sreedhara
Feb 15, 2012·Biochemical and Biophysical Research Communications·Sudarat YenjaiApinya Buranaprapuk
Sep 13, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Annelies SapTatjana N Parac-Vogt
Apr 27, 2005·Dalton Transactions : an International Journal of Inorganic Chemistry·Gaosheng YangLonggen Zhu
Jun 22, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Hong Giang T LyTatjana N Parac-Vogt
Mar 20, 2008·The Journal of Biological Chemistry·Ronny HellandHarald B Jensen
Oct 30, 2012·Chemical Science·Madeleine E KiefferSarah E Reisman
Aug 13, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Zorica D PetrovićSvetlana Marković
Jun 10, 2004·Journal of the American Chemical Society·Takeshi MotoyamaOsamu Yamauchi
Apr 16, 2003·Inorganic Chemistry·Lin ZhangLonggen Zhu
Jun 28, 2007·Environmental Science & Technology·Tatsuo MaruyamaMasahiro Goto
Mar 18, 2008·The Journal of Physical Chemistry. B·Francisco Tarazona-Vasquez, Perla B Balbuena

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