N-bromosuccinimide oxidation of dipeptides and their amino acids: Synthesis, kinetics and mechanistic studies

Linge Gowda, N. S. and Kumara, M. N. and Channe Gowda, D. and Rangappa, K. S. (2006) N-bromosuccinimide oxidation of dipeptides and their amino acids: Synthesis, kinetics and mechanistic studies. International Journal of Chemical Kinetics, 38 (6). pp. 376-385. ISSN 097-4601

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Abstract

Abstract Dipeptides (DP), namely valyl–glycine (Val–Gly), alanyl–proline (Ala–Pro), and valyl–proline (Val–Pro) were synthesized by classical solution phase methods and characterized. The kinetics of oxidation of amino acids (AA) and DP by N-bromosuccinimide (NBS) was studied in the presence of perchlorate ions in acidic medium at 28°C. The reaction was followed spectrophotometrically at λmax = 240 nm. The reactions follow identical kinetics, being first order each in NBS, AA, and DP. No effect on H+, reduction product succinimide, and ionic strength was observed. Effects of varying dielectric constant of the medium and addition of anions such as chloride and perchlorate were studied. Activation parameters have been computed. The oxidation products of the reaction were isolated and characterized. The proposed mechanism is consistent with the experimental results. An apparent correlation was noted between the rate of oxidation of AA and DP. © 2006 Wiley Periodicals, Inc. Int J Chem Kinet 38: 376–385, 2006

Item Type:	Article
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	LA manjunath user
Date Deposited:	19 Aug 2019 05:49
Last Modified:	10 Dec 2019 09:22
URI:	http://eprints.uni-mysore.ac.in/id/eprint/6736

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