title: Improved synthesis of lysine- and arginine-derived Amadori and Heyns products and in vitro measurement of their angiotensin I-converting enzyme inhibitory activity.
abstract: The L-lysine- and L-arginine-derived Amadori and Heyns products consisting of N-(1-deoxy-d-fructos-1-yl)amino acid and N-(2-deoxy-d-glucos-2-yl)amino acid were prepared by reaction of d-fructose and d-glucose with l-lysine hydrochloride and l-arginine hydrochloride using commercial zinc powder as deprotonating reagent and also as catalyst precursor in a simple synthetic route in high yield. These compounds were screened for angiotensin I-converting enzyme (ACE) inhibitory activity using a high-throughput colorimetric assay (utilizing porcine kidney ACE). The IC(50) values fall in the range of 1030-1175 μM, with N(α)-(1-deoxy-d-fructos-1-yl)arginine showing the best IC(50) value (1030 ± 38 μM). This study demonstrates an improved synthetic method for simple Amadori and Heyns products and their moderate ACE inhibitor activity.
authors.affiliation: Food Safety and Analytical Quality Control Laboratory, Central Food Technological Research Institute, Council of Scientific & Industrial Research, KRS Road, Mysore 570020, India.
authors.forename: Sudhanva M
authors.initials: SM
authors.lastname: Srinivas
authors.forename: Nanishankar V
authors.initials: NV
authors.lastname: Harohally
mesh_terms: D000806:Angiotensin-Converting Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D000818:Animals; D001120:Arginine / Q000737:chemistry*; D003847:Deoxyglucose / Q000737:chemistry; D005632:Fructose / Q000737:chemistry; D007202:Indicators and Reagents; D008239:Lysine / Q000737:chemistry*; D007703:Peptidyl-Dipeptidase A; D013552:Swine; D015032:Zinc
chemical_list: D000806:Angiotensin-Converting Enzyme Inhibitors; D007202:Indicators and Reagents; D005632:Fructose; D001120:Arginine; D003847:Deoxyglucose; D007703:Peptidyl-Dipeptidase A; D015032:Zinc; D008239:Lysine