Binding of copper (II) and other metal ions by lysinoalanine and related compounds and its significance for food safety
- Agricultural Research Service, Albany, CA (USA)
Acid-base equilibrium constants for the five ionizable groups and metal ion (Ca{sup 2+}, Mn{sup 2+}, Fe{sup 2+}, Co{sup 2+}, Ni{sup 2+}, Cu{sup +}, Zn{sup 2+}, Cd{sup 2+}, Hg{sup 2+}) binding constants of N{epsilon}-(2-amino-2-carboxyethyl)-L-lysine (lysino-alanine, LAL) have been determined at 25{degree}C and 0.16 M ionic strength by potentiometric titration. Less extensive data are reported for the related compounds DL-2,3-diaminopropanoic acid (DAPA), 3-((2-phenylethyl)amino)-DL-alanine (PEAA), and L-lanthionine (LAN), three other unnatural amino acids also formed during food processing. These unnatural amino acids are sufficiently strong chelators to influence copper transport by histidine in vivo at plasma levels of 49 {mu}M LAL, 23 {mu}M DAPA, 243 {mu}M PEAA, and 511 {mu}M LAN. Relatively high concentration of these compounds are calculated to be necessary for competitive binding of essential zinc ions and inactivation of carboxypeptidase A and other enzymes. Possible mechanisms for kidney damage by these dehydroalanine-derived copper chelators are discussed.
- OSTI ID:
- 5085851
- Journal Information:
- Journal of Agricultural and Food Chemistry; (USA), Journal Name: Journal of Agricultural and Food Chemistry; (USA) Vol. 36:4; ISSN JAFCA; ISSN 0021-8561
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
59 BASIC BIOLOGICAL SCIENCES
ALKALINE EARTH METAL COMPOUNDS
AMINO ACIDS
BIOCHEMICAL REACTION KINETICS
BODY
CADMIUM COMPOUNDS
CALCIUM COMPOUNDS
CARBOXYLIC ACIDS
CHELATES
CHELATING AGENTS
COBALT COMPOUNDS
COMPLEXES
COPPER COMPOUNDS
ELEMENTS
ENZYME ACTIVITY
FOOD PROCESSING
INACTIVATION
INJURIES
IRON COMPOUNDS
KIDNEYS
KINETICS
MANGANESE COMPOUNDS
MERCURY COMPOUNDS
METALS
NICKEL COMPOUNDS
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANS
PROCESSING
REACTION KINETICS
SAFETY
TRANSITION ELEMENT COMPOUNDS
ZINC COMPOUNDS