Lysinoalanine (LAL) and ornithinoalanine (OAL) are unnatural amino acids that can be formed in food submitted to thermal treatment, especially in alkaline conditions. The paper presents an optimization of the synthetic procedure for the preparation of a standard of OAL that could be very useful to study the toxicological and nutritional consequences of the presence of OAL in food. In the meantime, it was possible to develop a method based on nuclear magnetic resonance for the diastereomeric characterization of LAL and OAL without derivatization. Interest in this method is based on the known differences in the nephrotoxicity of the two diastereisomers of LAL.

Optimization of the Synthesis of the Cross-Linked Amino Acid Ornithinoalanine and Nuclear Magnetic Resonance Characterization of Lysinoalanine and Ornithinoalanine / G. Boschin, L. Scaglioni, A. Arnoldi. - In: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. - ISSN 0021-8561. - 47:3(1999), pp. 939-944.

Optimization of the Synthesis of the Cross-Linked Amino Acid Ornithinoalanine and Nuclear Magnetic Resonance Characterization of Lysinoalanine and Ornithinoalanine

G. Boschin
Primo
;
L. Scaglioni
Secondo
;
A. Arnoldi
Ultimo
1999

Abstract

Lysinoalanine (LAL) and ornithinoalanine (OAL) are unnatural amino acids that can be formed in food submitted to thermal treatment, especially in alkaline conditions. The paper presents an optimization of the synthetic procedure for the preparation of a standard of OAL that could be very useful to study the toxicological and nutritional consequences of the presence of OAL in food. In the meantime, it was possible to develop a method based on nuclear magnetic resonance for the diastereomeric characterization of LAL and OAL without derivatization. Interest in this method is based on the known differences in the nephrotoxicity of the two diastereisomers of LAL.
Diastereoisomers; Lysinoalanine; NMR analysis; Ornithinoalanine; Synthesis
Settore CHIM/10 - Chimica degli Alimenti
1999
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/181906
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