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High pressure induced hydrolysis at C-terminus of peptide derivatives yielding bioactive peptides

If the cyclization of a peptide is associated with a volume reduction, pressure should displace the reaction equilibrium in the direction of a lower volume. Here, results in model solutions are considered, showing a pressure-accelerated transformation of linear dipeptides with reactive C-terminals....

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Hauptverfasser: Fernández, Avelina (VerfasserIn) , Zöller, Heike (VerfasserIn) , Butz, Peter (VerfasserIn) , Stärke, Joachim (VerfasserIn) , Tauscher, Bernhard (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: March 2006
In: Food chemistry
Year: 2006, Jahrgang: 95, Heft: 2, Pages: 301-306
ISSN:1873-7072
DOI:10.1016/j.foodchem.2005.01.010
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1016/j.foodchem.2005.01.010
Verlag, lizenzpflichtig, Volltext: https://www.sciencedirect.com/science/article/pii/S0308814605000798
Volltext
Verfasserangaben:A. Fernández García, H. Zöller, P. Butz, J. Stärke, B. Tauscher
Beschreibung
Zusammenfassung:If the cyclization of a peptide is associated with a volume reduction, pressure should displace the reaction equilibrium in the direction of a lower volume. Here, results in model solutions are considered, showing a pressure-accelerated transformation of linear dipeptides with reactive C-terminals. The theorised cyclization of dipeptides after hydrolysis of the C-terminal amide H-Leu-Gly-NH2 or methyl ester groups H-Leu-Gly-OMe and H-Leu-Gly-OtBu was found to be significantly accelerated during application of combined pressure/temperature treatments up to 600-800MPa and 60-80°C. Yields were dependent on the nature of the reactive site. Products of those reactions were identified as H-Leu-Gly-OH and cyclo(Leu-Gly), which is a bioactive dipeptide. The dipeptide amide yielded only trace concentrations of the amino acid H-Leu-OH and the linear dipeptide. Steric hindrance prevented a pressure induced cyclisation of a dipeptide with tert-butyl ester at the C-terminus, and only the linear peptide H-Leu-Gly-OH was formed.
Beschreibung:Online veröffentlicht: 10. März 2005
Gesehen am 08.01.2024
Beschreibung:Online Resource
ISSN:1873-7072
DOI:10.1016/j.foodchem.2005.01.010

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