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Degradation Kinetics of L-alanyl-L-glutamine and Its Derivatives in Aqueous Solution

Degradation Kinetics of L-alanyl-L-glutamine and Its Derivatives in Aqueous Solution

K Arii, T Kai, Y Kokuba

Eur J Pharm Sci. 1999 Jan;7(2):107-12.

PMID: 9845788

Abstract:

The degradation kinetics of five glutamine dipeptides in aqueous solution, i.e. glycyl-L-glutamine (Gly-Gln), L-alanyl-L-glutamine (Ala-Gln), L-valyl-L-glutamine (Val-Gln), L-leucyl-L-glutamine (Leu-Gln) and L-isoleucyl-L-glutamine (Ile-Gln), were studied. Stability tests were performed using a stability-indicating high-performance liquid chromatographic assay. Two different Ala-Gln degradation routes, i.e. the cleavage of a peptide bond and the deamination of an amide group, were observed. The degradation was adequately described by pseudo-first-order kinetics. The maximum stability of Ala-Gln was obtained at an approximate pH of 6.0. The pH-rate profile described by specific acid-base catalysis and hydrolysis by water molecules agreed with the experimental results. The activation energy of Ala-Gln at pH 6.0 was determined to be 27. 1kcal mol-1, and the shelf-life (90% remaining) at 25 and 40 degrees C was predicted to be 5.3 years and 7.1 months, respectively. The rate constants of the glutamine dipeptides were influenced by the N-terminal amino acid residue and decreased in the order: Gly-Gln, Ala-Gln, Leu-Gln, Val-Gln and Ile-Gln.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP39537230-A	L-Alanyl-L-glutamine		39537-23-0	Price

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