Conformational studies of Angiotensin II and analogues in dimethyl sulfoxide by 1H NMR: Lability and intramolecular interactions of the tyrosine hydroxyl and histidine imidazole NH protons

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Title:Conformational studies of Angiotensin II and analogues in dimethyl sulfoxide by 1H NMR: Lability and intramolecular interactions of the tyrosine hydroxyl and histidine imidazole NH protons
Creators:
Matsoukas, John
Bigam, Glen
Yamdagni, Raghav
Moore, Graham J.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 6, pp. 1348-1357

Abstract

<sup>1</sup>H NMR studies in dimethyl sulfoxide illustrate that the tyrosine hydroxyl proton and the histidine imidazole NH proton in [Sar<sup>1</sup>]ANGII and analogues are labile at neutral pH but not at acid pH. This is attributable to intramolecular interactions of these groups with negatively charged groups. Methylation or elimination of the Tyr hydroxyl in [Sar<sup>1</sup>]ANGII and analogues, invokes a small but consistent deshielding effect on the His C-2 and C-4 protons, suggesting an interaction between the Tyr hydroxyl and the His ring. Nuclear Overhauser Effect (NOE) enhancement experiments in {Sar<sup>1</sup>]ANGII and the Sarmesin analogue [Des<sup>1</sup>, Tyr(Me)<sup>4</sup>]ANGII, support the Tyr/His interaction and confirm the presence of a <i>trans</i> His-Pro peptide bond.

Title:Conformational studies of Angiotensin II and analogues in dimethyl sulfoxide by 1H NMR: Lability and intramolecular interactions of the tyrosine hydroxyl and histidine imidazole NH protons
Creators:
Matsoukas, John
Bigam, Glen
Yamdagni, Raghav
Moore, Graham J.
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:6
Page Range:pp. 1348-1357
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19911348UNSPECIFIED
ID Code:5057
Item Type:Article
Deposited On:22 Feb 2010 11:29
Last Modified:22 Feb 2010 10:29

Citation

Matsoukas, John; Bigam, Glen; Yamdagni, Raghav; Moore, Graham J. (1991) Conformational studies of Angiotensin II and analogues in dimethyl sulfoxide by 1H NMR: Lability and intramolecular interactions of the tyrosine hydroxyl and histidine imidazole NH protons. Collection of Czechoslovak Chemical Communications, 56 (6). pp. 1348-1357. ISSN 0010-0765

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