PMID: 11606184Oct 19, 2001Paper

The biosynthesis of ovothiol A (N-methyl-4-mercaptohistidine). Identification of S-(4'-L-histidyl)-L-cysteine sulfoxide as an intermediate and the products of the sulfoxide lyase reaction

European Journal of Biochemistry
R N VogtD J Steenkamp

Abstract

Crude extracts of Crithidia fasciculata catalyse the formation of 4-mercapto-L-histidine, an intermediate in the biosynthesis of ovothiol A (N1-methyl-4-mercaptohistidine), in the presence of histidine, cysteine, Fe2+ and pyridoxal phosphate. This activity was present in a 35-55% ammonium sulfate fraction that was shown to produce a transsulfuration intermediate in the absence of pyridoxal phosphate. The transsulfuration intermediate was isolated and identified as S-(4'-L-histidyl)-L-cysteine sulfoxide. The synthase activity, partially purified by anion-exchange chromatography, was shown to require oxygen and could be used to synthesize a number of isotopically labeled S-(4'-L-histidyl)-L-cysteine sulfoxides. Sulfoxide lyase activity was partially resolved from the synthase by anion-exchange chromatography. The phenylhydrazone of the product derived from the cysteine moiety of the sulfoxide coeluted with the phenylhydrazone of pyruvate on HPLC, but this assignment could not be confirmed by mass spectral analysis. S-(4'-[14C]L-histidyl)-[U-13C3,15N]L-cysteine sulfoxide was synthesized and converted to products of the lyase reaction in the presence of lactate dehydrogenase and NADH. The 13C-labeled product was identified by 13C-N...Continue Reading

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Citations

Apr 18, 2013·The Journal of Physical Chemistry. a·Phil De LunaJames W Gauld
Apr 24, 2002·Antioxidants & Redox Signaling·Daniel J Steenkamp
Nov 8, 2011·Antioxidants & Redox Signaling·R Luise Krauth-Siegel, Alejandro E Leroux
May 20, 2003·Biological Chemistry·R Luise Krauth-SiegelHeide Schmidt
Jan 5, 2014·International Journal of Molecular Sciences·Rami GheribJames W Gauld
Feb 11, 2014·Analytical and Bioanalytical Chemistry·Arash MirzahosseiniBéla Noszál
Feb 27, 2016·Scientific Reports·Immacolata CastellanoAnna Palumbo
Apr 19, 2017·Chemical Reviews·Kyle L DunbarChristian Hertweck
Sep 2, 2017·Chembiochem : a European Journal of Chemical Biology·Cangsong Liao, Florian P Seebeck
Nov 28, 2019·Proceedings. Biological Sciences·Marco GerdolImmacolata Castellano
Jul 28, 2018·Natural Product Reports·Immacolata Castellano, Florian P Seebeck
Jul 24, 2013·Chemical Communications : Chem Comm·Gabriel T M Mashabela, Florian P Seebeck
Nov 27, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Danushka M EkanayakeAdam T Fiedler
Jan 21, 2011·Journal of the American Chemical Society·Andrea Braunshausen, Florian P Seebeck
Jul 18, 2021·Genome Biology and Evolution·Mariarita BrancaccioImmacolata Castellano

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