Copper(II) and cobalt(II) affinities of LL- and LD-lysinoalanine diastereomers: Implications for food safety and nutrition

Journal Article · · Journal of Agricultural and Food Chemistry; (USA)

DOI:https://doi.org/10.1021/jf00085a029· OSTI ID:6935953

Friedman, M; Pearce, K N ^[1]

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1. Department of Agriculture, Albany, CA (USA)

L-N{sup 6}-(2-Amino-2-carboxyethyl)-L-lysine (LL-lysinoalanine, LL-LAL) and D-N{sup 6}-(2-amino-2-carboxyethyl)-L-lysine (LD-lysinoalanine, LD-LAL), which are found in many processed foods, have been studied by spectrophotometric and potentiometric techniques. Molar optical rotation data were used to calculate the stereochemical composition of a synthetic mixture of both compounds as 56:44 LD to LL. The two diastereomers have similar acid ionization constants but differ somewhat in their affinities for copper(II) ions, as measured by their binding constants. This difference may be related to the reported differences in the ability of the isomers to induce kidney damage in rats. These results support a mechanism for the biological effects of LAL based on its ability to strongly chelate copper ions. Limited studies on the binding of LAL to cobalt(II) ions suggest that they form a yellow dioxygen complex with a possible structure of Co{sub 2}(LAL){sub 3}O{sub 2}. The possible significance of these findings for food safety and nutrition is discussed.

• OSTI ID: 6935953
• Journal Information: Journal of Agricultural and Food Chemistry; (USA), Journal Name: Journal of Agricultural and Food Chemistry; (USA) Vol. 37:1; ISSN JAFCA; ISSN 0021-8561
• Country of Publication: United States
• Language: English

Related Subjects

553004 -- Agriculture & Food Technology-- Food Protection & Preservation-- (1987-)
560300* -- Chemicals Metabolism & Toxicology
60 APPLIED LIFE SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AFFINITY
AMINO ACIDS
ANIMALS
BIOCHEMICAL REACTION KINETICS
BODY
CARBOXYLIC ACIDS
COBALT COMPOUNDS
COPPER COMPOUNDS
FOOD PROCESSING
HAZARDS
HEALTH HAZARDS
INJURIES
KIDNEYS
KINETICS
MAMMALS
NUTRITION
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANS
PROCESSING
PROTEINS
RATS
REACTION KINETICS
RODENTS
SAFETY
STEREOCHEMISTRY
STRUCTURE-ACTIVITY RELATIONSHIPS
TOXICITY
TRANSITION ELEMENT COMPOUNDS
VERTEBRATES