Abstract
γ-Glutamyl derivatives of sulfur amino acids have been prepared in multigram scale starting from readily available starting materials. The synthesis comprises two one-pot operations, both consisting of two reactions. In the first operation, N-phtaloyl-l-glutamic acid anhydride is obtained from l-glutamic acid and phtalic anhydride. In the second one, N-phtaloyl-l-glutamic acid anhydride is used to acylate amino acids and the N-phtaloyl protecting group is removed. The described approach offers a viable entry to γ-glutamyl derivatives of sulfur-containing amino acids with flavor-enhancer and nutraceutical properties.
Highlights
Introduction γGlutamyl derivatives are compounds in which the amino group of an amino acid or theN-terminal of a short peptide is acylated by the γ-carboxyl carbon of a glutamic acid residue.They are naturally occurring compounds; glutathione (γ-glutamylcysteinylglycine, GSH) is the most widespread thiol in cells, and various γ-glutamyl amino acids are common constituents of plants [1,2,3,4].γ-Glutamyl derivatives of amino acids have altered chemico-physical and organoleptic properties, yet representing precursors of the parent compounds [5].Several γ-glutamyl amino acids are taste-active compounds with kokumi properties found in many foods [6,7]
Following our interest in taste-active compounds of natural origin [18], we report here a multigram scale conversion of the sulfur-containing amino acids S-methyl-l-cysteine (2), S-allyl-l-cysteine (3), S-benzyl-l-cysteine (4), and methionine (5) into the corresponding γ-glutamyl derivatives 8–11 through two one-pot operations, each involving two synthetic steps
N-phtaloyl-l-glutamic acid and its anhydride 1 are both commercially available, they are rather expensive products and we decided to synthesize them from l-glutamic acid 6 and phtalic anhydride 7
Summary
Introduction γGlutamyl derivatives are compounds in which the amino group of an amino acid or theN-terminal of a short peptide is acylated by the γ-carboxyl carbon of a glutamic acid residue.They are naturally occurring compounds; glutathione (γ-glutamylcysteinylglycine, GSH) is the most widespread thiol in cells, and various γ-glutamyl amino acids are common constituents of plants [1,2,3,4].γ-Glutamyl derivatives of amino acids have altered chemico-physical and organoleptic properties, yet representing precursors of the parent compounds [5].Several γ-glutamyl amino acids are taste-active compounds with kokumi properties found in many foods [6,7]. N-terminal of a short peptide is acylated by the γ-carboxyl carbon of a glutamic acid residue. They are naturally occurring compounds; glutathione (γ-glutamylcysteinylglycine, GSH) is the most widespread thiol in cells, and various γ-glutamyl amino acids are common constituents of plants [1,2,3,4]. Several γ-glutamyl amino acids are taste-active compounds with kokumi properties found in many foods [6,7]. Biological activities exerted by some γ-glutamyl derivatives are known [10,11], and the fact that such compounds are constituents of food vegetables led to them being considered as nutraceuticals
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