Ternary palladium(II)-glycylmethionine-nucleobase complexes: Solution studies and crystal structure of the 9-methylguanine compound

Markus Wienken, Attila Kiss, I. Sóvágó, Edda C. Fusch, Bernhard Lippert

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Ternary complex formation between model nucleobases and [Pd(gly-L-met)] 1 (gly-L-met = dianion of glycylmethionine, deprotonated at the amide N and at the met carboxylate terminus) has been studied by 1H NMR spectroscopy and potentiometry. A representative example, [Pd(gly-L-metH)(Hmgua)]NO3·H2O 3 (Hmgua = 9-methylguanine), has been characterized by X-ray crystallography. Co-ordination of Pd is through the terminal amino group of the glycyl entity, the deprotonated amide nitrogen, S of the methionine, and N7 of the purine nucleobase. The carboxylic acid group of methionine is protonated. In aqueous solution binding of Pd to other nucleobases occurs via N3 in the case of 1-methylcytosine (Hmcyt) and of deprotonated 1-methyluracil, N7 of 9-ethylguanine (Hegua) or N1, N7/N1 of the guanine anion (egua). Discrete rotamers form on binding of Pd to N3 of the pyrimidine nucleobases and to N1 of the guanine. The gly-L-metH resonances provide no evidence for the existence of stable diastereomers, suggesting that inversion at the chiral S atom of met is fast. In contrast, both [Pt(gly-L-metH)Cl] and its ternary derivative with Hmcyt appear to be present in solution as diastereomeric mixtures. Stability constants have been determined for ternary complexes formed from 1 and [Pd(gly-L-metH)Cl], respectively, with nucleobases.

Original languageEnglish
Pages (from-to)563-568
Number of pages6
JournalJournal of the Chemical Society, Dalton Transactions
Issue number4
Publication statusPublished - Feb 21 1997

Fingerprint

Guanine
Palladium
Amides
Methionine
Crystal structure
X ray crystallography
Carboxylic Acids
Nuclear magnetic resonance spectroscopy
Anions
Nitrogen
Derivatives
Atoms
9-methylguanine
pyrimidine
1-methyluracil
purine
9-ethylguanine
1-methylcytosine

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Ternary palladium(II)-glycylmethionine-nucleobase complexes : Solution studies and crystal structure of the 9-methylguanine compound. / Wienken, Markus; Kiss, Attila; Sóvágó, I.; Fusch, Edda C.; Lippert, Bernhard.

In: Journal of the Chemical Society, Dalton Transactions, No. 4, 21.02.1997, p. 563-568.

Research output: Contribution to journalArticle

@article{6b19e68a36e0483288f442a31102f5af,
title = "Ternary palladium(II)-glycylmethionine-nucleobase complexes: Solution studies and crystal structure of the 9-methylguanine compound",
abstract = "Ternary complex formation between model nucleobases and [Pd(gly-L-met)] 1 (gly-L-met = dianion of glycylmethionine, deprotonated at the amide N and at the met carboxylate terminus) has been studied by 1H NMR spectroscopy and potentiometry. A representative example, [Pd(gly-L-metH)(Hmgua)]NO3·H2O 3 (Hmgua = 9-methylguanine), has been characterized by X-ray crystallography. Co-ordination of Pd is through the terminal amino group of the glycyl entity, the deprotonated amide nitrogen, S of the methionine, and N7 of the purine nucleobase. The carboxylic acid group of methionine is protonated. In aqueous solution binding of Pd to other nucleobases occurs via N3 in the case of 1-methylcytosine (Hmcyt) and of deprotonated 1-methyluracil, N7 of 9-ethylguanine (Hegua) or N1, N7/N1 of the guanine anion (egua). Discrete rotamers form on binding of Pd to N3 of the pyrimidine nucleobases and to N1 of the guanine. The gly-L-metH resonances provide no evidence for the existence of stable diastereomers, suggesting that inversion at the chiral S atom of met is fast. In contrast, both [Pt(gly-L-metH)Cl] and its ternary derivative with Hmcyt appear to be present in solution as diastereomeric mixtures. Stability constants have been determined for ternary complexes formed from 1 and [Pd(gly-L-metH)Cl], respectively, with nucleobases.",
author = "Markus Wienken and Attila Kiss and I. S{\'o}v{\'a}g{\'o} and Fusch, {Edda C.} and Bernhard Lippert",
year = "1997",
month = "2",
day = "21",
language = "English",
pages = "563--568",
journal = "Dalton Transactions",
issn = "1472-7773",
publisher = "Royal Society of Chemistry",
number = "4",

}

TY - JOUR

T1 - Ternary palladium(II)-glycylmethionine-nucleobase complexes

T2 - Solution studies and crystal structure of the 9-methylguanine compound

AU - Wienken, Markus

AU - Kiss, Attila

AU - Sóvágó, I.

AU - Fusch, Edda C.

AU - Lippert, Bernhard

PY - 1997/2/21

Y1 - 1997/2/21

N2 - Ternary complex formation between model nucleobases and [Pd(gly-L-met)] 1 (gly-L-met = dianion of glycylmethionine, deprotonated at the amide N and at the met carboxylate terminus) has been studied by 1H NMR spectroscopy and potentiometry. A representative example, [Pd(gly-L-metH)(Hmgua)]NO3·H2O 3 (Hmgua = 9-methylguanine), has been characterized by X-ray crystallography. Co-ordination of Pd is through the terminal amino group of the glycyl entity, the deprotonated amide nitrogen, S of the methionine, and N7 of the purine nucleobase. The carboxylic acid group of methionine is protonated. In aqueous solution binding of Pd to other nucleobases occurs via N3 in the case of 1-methylcytosine (Hmcyt) and of deprotonated 1-methyluracil, N7 of 9-ethylguanine (Hegua) or N1, N7/N1 of the guanine anion (egua). Discrete rotamers form on binding of Pd to N3 of the pyrimidine nucleobases and to N1 of the guanine. The gly-L-metH resonances provide no evidence for the existence of stable diastereomers, suggesting that inversion at the chiral S atom of met is fast. In contrast, both [Pt(gly-L-metH)Cl] and its ternary derivative with Hmcyt appear to be present in solution as diastereomeric mixtures. Stability constants have been determined for ternary complexes formed from 1 and [Pd(gly-L-metH)Cl], respectively, with nucleobases.

AB - Ternary complex formation between model nucleobases and [Pd(gly-L-met)] 1 (gly-L-met = dianion of glycylmethionine, deprotonated at the amide N and at the met carboxylate terminus) has been studied by 1H NMR spectroscopy and potentiometry. A representative example, [Pd(gly-L-metH)(Hmgua)]NO3·H2O 3 (Hmgua = 9-methylguanine), has been characterized by X-ray crystallography. Co-ordination of Pd is through the terminal amino group of the glycyl entity, the deprotonated amide nitrogen, S of the methionine, and N7 of the purine nucleobase. The carboxylic acid group of methionine is protonated. In aqueous solution binding of Pd to other nucleobases occurs via N3 in the case of 1-methylcytosine (Hmcyt) and of deprotonated 1-methyluracil, N7 of 9-ethylguanine (Hegua) or N1, N7/N1 of the guanine anion (egua). Discrete rotamers form on binding of Pd to N3 of the pyrimidine nucleobases and to N1 of the guanine. The gly-L-metH resonances provide no evidence for the existence of stable diastereomers, suggesting that inversion at the chiral S atom of met is fast. In contrast, both [Pt(gly-L-metH)Cl] and its ternary derivative with Hmcyt appear to be present in solution as diastereomeric mixtures. Stability constants have been determined for ternary complexes formed from 1 and [Pd(gly-L-metH)Cl], respectively, with nucleobases.

UR - http://www.scopus.com/inward/record.url?scp=33748507991&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33748507991&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:33748507991

SP - 563

EP - 568

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1472-7773

IS - 4

ER -