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Structural effects on the N-nitrosation of amino acids

✍ Scribed by Rafael Gil; Julio Casado; Carmen Izquierdo

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 165 KB
Volume: 29
Category: Article
ISSN: 0538-8066
DOI: 10.1002/(sici)1097-4601(1997)29:7<495::aid-kin3>3.0.co;2-p

No coin nor oath required. For personal study only.

✦ Synopsis

The relative importance of three different routes for the N-nitrosation of amino acids (nitrosation by N 2 O 3 , by and by intramolecular migration of the nitroso group from the initially nitrosated carboxylate group) was investigated for methylaminobutyric acid, methylaminoisobutyric acid, azetidine-2-carboxylic acid, azetidine-3-carboxylic acid, indoline carboxylic acid, and phenylaminoacetic acid. Reaction kinetics were determined by the initial rate and Guggenheim methods, by spectrophotometric monitoring of the formation of nitroso amino acid. Kinetic parameters were calculated using a nonlinear optimization algorithm based on Marquardt's method. In the experimental rate equation the dominant term corresponds to nitrosation by dinitrogen trioxide, which experiments at various temperatures show to take place via an ordered transition state. Nitrosation by intramolecular migration is significant for substrates facilitating the formation of a transition state structure with a 5-or 6-membered ring.

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