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Methylated derivatives of l-tyrosine in reaction catalyzed by l-amino acid oxidase: isotope and inhibitory effects

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dc.abstract.enL-Amino acid oxidase (LAAO) is widely distributed in nature and shows important biological activity. It induces cell apoptosis and has antibacterial properties. This study was designed to investigate the effect of methyl substituent on its activity as methylated derivatives of L-tyrosine, labelled with short-lived B1 emitters, have been used in oncological diagnostics. To study isotope effects in the oxidative deamination of O-methyl-L-tyrosine, the deuterated sotopomer, i.e. O-methyl-[2-2H]-L-tyrosine, was synthesized by isotope exchange, catalyzed enzymatically by tryptophanase. Isotope effects were determined using the spectrophotometric non-competitive method. The values of isotope effects indicate that the a-C–H bond cleavage occurs in the rate determining step of the investigated reaction and a-hydrogen plays a role in the substrate binding process at the enzyme active site. The inhibitory effect on LAAO activity was studied with a-methyl-L-tyrosine and N-methyl-L-tyrosine. The mode of inhibition was determined based on Lineweavear–Burk plots intersections. a-Methyl-Ltyrosine has been found a mixed type inhibitor of the investigated enzyme, whereas N-methyl-L-tyrosine is a non-competitive inhibitor of LAAO.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorPająk, Małgorzata
dc.date.accessioned2024-01-25T11:28:20Z
dc.date.available2024-01-25T11:28:20Z
dc.date.issued2020
dc.description.financePublikacja bezkosztowa
dc.description.number5
dc.description.volume168
dc.identifier.doi10.1093/JB/MVAA066
dc.identifier.issn0021-924X
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/112364
dc.identifier.weblinkhttp://academic.oup.com/jb/advance-article-pdf/doi/10.1093/jb/mvaa066/33646478/mvaa066.pdf
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofJournal of Biochemistry
dc.relation.pages509-514
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.subject.ena-methyl-L-tyrosine
dc.subject.enisotope effects
dc.subject.enLamino acid oxidase inhibition
dc.subject.enN-methyl-L-tyrosine
dc.subject.enO-methyl-L-tyrosine
dc.titleMethylated derivatives of l-tyrosine in reaction catalyzed by l-amino acid oxidase: isotope and inhibitory effects
dc.typeJournalArticle
dspace.entity.typePublication