Thiolate anchor in organotin(iv) induced amide deprotonation: Equilibrium and NMR spectroscopic studies on dimethyltin(iv) complexes formed with N-(2-mercaptopropionyl)glycine and l-alanyl-glycine

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Abstract

The coordination properties of the simple dipeptide l-alanyl-glycine (Ala-Gly) towards dimethyltin(iv) cation have been compared with its mercapto analogue N-(2-mercaptopropionyl)glycine (MPGly), using potentiometric,1H and13C NMR spectroscopic methods. The replacement of the terminal amino group of Ala-Gly by a thiol group (MPGly) induces fundamental changes in the coordination processes and in the speciation of metal complexes, though the composition of the species formed is identical. The considerably higher stability of the MPGly complexes is due to the outstanding affinity of dimethyltin(iv) cation toward sulfur donor atoms. In the MLH and ML complexes, formed in the acidic pH range, monodentate carboxylate and thiolate coordination has been observed for Ala-Gly and MPGly, respectively. Therefore, different donor groups in the case of the two ligands assist the metal promoted deprotonation of amide nitrogen. Our data provide the first example, that thiolate can act as an anchoring group in the diorganotin(iv) induced amide deprotonation.

Original languageEnglish
Pages (from-to)2912-2916
Number of pages5
JournalJournal of the Chemical Society. Dalton Transactions
Volume3
Issue number14
DOIs
Publication statusPublished - Jul 9 2003

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Deprotonation
Anchors
Amides
Glycine
Nuclear magnetic resonance
Cations
Dipeptides
Coordination Complexes
dimethyltin
Sulfur
Sulfhydryl Compounds
Nitrogen
Metals
Ligands
Atoms
Chemical analysis

Keywords

  • Amino acids, peptides, proteins
  • Organometallic
  • Solution studies
  • Stability constants
  • Tin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Thiolate anchor in organotin(iv) induced amide deprotonation: Equilibrium and NMR spectroscopic studies on dimethyltin(iv) complexes formed with N-(2-mercaptopropionyl)glycine and l-alanyl-glycine",
abstract = "The coordination properties of the simple dipeptide l-alanyl-glycine (Ala-Gly) towards dimethyltin(iv) cation have been compared with its mercapto analogue N-(2-mercaptopropionyl)glycine (MPGly), using potentiometric,1H and13C NMR spectroscopic methods. The replacement of the terminal amino group of Ala-Gly by a thiol group (MPGly) induces fundamental changes in the coordination processes and in the speciation of metal complexes, though the composition of the species formed is identical. The considerably higher stability of the MPGly complexes is due to the outstanding affinity of dimethyltin(iv) cation toward sulfur donor atoms. In the MLH and ML complexes, formed in the acidic pH range, monodentate carboxylate and thiolate coordination has been observed for Ala-Gly and MPGly, respectively. Therefore, different donor groups in the case of the two ligands assist the metal promoted deprotonation of amide nitrogen. Our data provide the first example, that thiolate can act as an anchoring group in the diorganotin(iv) induced amide deprotonation.",
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AU - Gajda-Schrantz, K.

AU - Jancsó, A.

AU - Pettinari, C.

AU - Gajda, T.

PY - 2003/7/9

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N2 - The coordination properties of the simple dipeptide l-alanyl-glycine (Ala-Gly) towards dimethyltin(iv) cation have been compared with its mercapto analogue N-(2-mercaptopropionyl)glycine (MPGly), using potentiometric,1H and13C NMR spectroscopic methods. The replacement of the terminal amino group of Ala-Gly by a thiol group (MPGly) induces fundamental changes in the coordination processes and in the speciation of metal complexes, though the composition of the species formed is identical. The considerably higher stability of the MPGly complexes is due to the outstanding affinity of dimethyltin(iv) cation toward sulfur donor atoms. In the MLH and ML complexes, formed in the acidic pH range, monodentate carboxylate and thiolate coordination has been observed for Ala-Gly and MPGly, respectively. Therefore, different donor groups in the case of the two ligands assist the metal promoted deprotonation of amide nitrogen. Our data provide the first example, that thiolate can act as an anchoring group in the diorganotin(iv) induced amide deprotonation.

AB - The coordination properties of the simple dipeptide l-alanyl-glycine (Ala-Gly) towards dimethyltin(iv) cation have been compared with its mercapto analogue N-(2-mercaptopropionyl)glycine (MPGly), using potentiometric,1H and13C NMR spectroscopic methods. The replacement of the terminal amino group of Ala-Gly by a thiol group (MPGly) induces fundamental changes in the coordination processes and in the speciation of metal complexes, though the composition of the species formed is identical. The considerably higher stability of the MPGly complexes is due to the outstanding affinity of dimethyltin(iv) cation toward sulfur donor atoms. In the MLH and ML complexes, formed in the acidic pH range, monodentate carboxylate and thiolate coordination has been observed for Ala-Gly and MPGly, respectively. Therefore, different donor groups in the case of the two ligands assist the metal promoted deprotonation of amide nitrogen. Our data provide the first example, that thiolate can act as an anchoring group in the diorganotin(iv) induced amide deprotonation.

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