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Protonation equilibria of glycylglycine and histamine in aqueous solution of an anionic surfactant  

Posted on 26. February, 2014.

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Peptides are an amazing, diverse and multi-faceted class of compounds constructed from relatively simple building blocks, the amino acids. They are components of tissues and exhibit a remarkable range of biological properties acting as antibiotics, hormones, food additives, poisons or pain-killers.

Several metal complexes containing peptide groups have displayed diverse pharmacological activities. For instance, copper complexes with amino acids and peptides as ligands show anti-inflammatory and cytostatic activities.

In Investigations involving the peptides in acid-base reactions, small peptides have attracted great attention in relation to the chemistry because these compounds are usually considered as good model systems to attain a better insight into the characteristics of naturally occurring metalloproteins.

Much data are available on the protonation and stability constants of the amino acids and simple peptides in water and organic solvents. However, the protonation constants of amino acids and peptides in these organic solvents are often different from those in water, as these media tend to be lipophilic rather than hydrophilic.

Little is known about the chemistry of amino acids and simple peptides in mixed solvents, in regard to their protonation constants and experiments have shown that one solvent alone is not an ideal model for in vivo reactions.

In this paper, the protonation constants of glycylglycine and histamine have been determined pH-metrically in aqua-surfactant mixtures containing SLS frequently used as media in biochemistry and biology laboratories. 

Read the entire article in Chemical Speciation and Bioavailability, Volume 26, Number 1, February 2014 , pp. 52-58.
DOI: 10.3184/095422914X13886846341174

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