The biosynthesis of ovothiol A (N 1-methyl-4-mercaptohistidine) identification of S-(40′-L-histidyl)-L-cysteine sulfoxide as an intermediate and the products of the sulfoxide lyase reaction

European Journal of Biochemistry

Volumn 268, Issue 20, 2001, Pages 5229-5241

  Vogt, Ryan N ^a   Spies, Hendrik S C ^b   Steenkamp, Daniel J ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

^b STELLENBOSCH UNIVERSITY   (South Africa)

Author keywords

Biosynthesis; Ovothiol A; Transsulfuration; Trypanosomatid

Indexed keywords

(4' HISTIDYL)CYSTEINE SULFOXIDE; AMMONIUM SULFATE; CARBON 14; DITHIOTHREITOL; LACTATE DEHYDROGENASE; LYASE; OVOTHIOL A; OXYGEN; PHENYLHYDRAZONE DERIVATIVE; PYRIDOXAL 5 PHOSPHATE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; SULFOXIDE; SYNTHETASE; TRITIUM; UNCLASSIFIED DRUG;

ANIMAL CELL; ANION EXCHANGE CHROMATOGRAPHY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME MECHANISM; ENZYME SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN SYNTHESIS;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, ION EXCHANGE; CRITHIDIA FASCICULATA; CYSTEINE; DIPEPTIDES; DITHIOTHREITOL; LYASES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; METHYLHISTIDINES; METHYLTRANSFERASES; PYRIDOXAL PHOSPHATE; SULFOXIDES; TIME FACTORS;

EID: 0034798258     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.0014-2956.2001.02444.x     Document Type: Article

References (33)

1. Ovothiols: Biological and chemical perspectives
2. 2 oxidoreductase activity
3. Ovothiols as biological antioxidants. The thiol groups of ovothiol and glutathione are chemically distinct
4. Heterocyclic thiols as antioxidants: Why ovothiol C is a better antioxidant than ergothioneine
5. 4-Mercaptoimidazoles derived from the naturally occurring antioxidant ovothiols 1. Antioxidant properties
6. Ovothiol replaces glutathione peroxidase as a hydrogen peroxide scavenger in sea urchin eggs
7. Antioxidant actions of ovothiol-derived 4-mercaptoimida-zoles: Glutathione peroxidase activity and protection against peroxynitrite-induced damage
8. The control of oxidant stress at fertilization
9. L-Ovothiol A: The egg release pheromone of the marine polychate Platynereis dumerilii: Annelida: Polychaeta
10. L-1-N-Methyl-4-mercaptohistidine disulfide, a potential endogenous regulator in the redox control of chloroplast coupling factor 1 in Dunaliella
11. Identification of a major low molecular mass thiol of the trypanosomatid Crithidia fasciculata as ovothiol A: Facile isolation and structural analysis of the bimane derivative
12. Thiols of intracellular pathogens: Identification of ovothiol A in Leishmania donovani and structural analysis of a novel thiol from Mycobacterium bovis
13. Ovothiol and trypanothione as antioxidants in trypanosomatids
14. Studies on the biosynthesis of ovothiol A. Identification of 4-mercaptohistidine as an intermediate
15. Participation of an intermediate sulfoxide in the enzymatic thiolation of the imidazole ring of hercynine to form ergothioneine
16. New fluorochromes for thiols: Maleimide and iodoacetamide derivatives of a 3-phenylcoumarin fluorophore
17. Purification and characterization of trypanothione reductase from Crithidia fasciculata, a newly discovered member of the family of disulfide-containing flavoprotein reductases
18. The use of 2,2′-dithiodipyridine in the determination of of glutathione and triphosphopyridine by enzymatic cycling
19. Contamination of plasma samples by plasticizers: Another source
20. High-performance liquid chromatographic determination of glyoxylic acid in urine
21. Catalytic formation of a nitrogenase iron-sulfur cluster
22. Escherichia coli contains a protein that is homologous in function and N-terminal sequence to the protein encoded by the nifS gene of Azotobacter vinelandii and that can participate in the synthesis of the Fe-S cluster of dihydroxy-acid dehydratase
23. The cysteine desulfurase, IscS, has a major role in in vivo Fe-S cluster formation in Escherichia coli
24. Evidence that ThI, an enzyme shared between thiamin and 4-thiouridine biosynthesis, may be a sulfurtransferase that proceeds through a persulfide intermediate
25. The iscS gene in Escherischia coli is required for the biosynthesis of 4-thiouridine, thiamin and NAD
26. Identification of the [Fe-S] cluster-binding residues of Escherichia coli biotin synthase
27. Evidence for cysteine persulfide as reaction product of L-cyst(e)ine C-S-lyase (C-DES) from Synechocystis
28. The reduction of sulfoxide by iodide/organic acid system in the solid state
29. Thiol-disulfide exchange is involved in the catalytic mechanism of peptide methionine sulfoxide reductase
30. Suppression of hypercholesterolemia in hepatoma-bearing rats by cabbage extract and its component, S-methyl-L-cysteine sulfoxide
31. Antiperoxide effect of S-allyl cysteine sulfoxide, an insulin secretagogue, in diabetic rats
32. Novel priming compounds of cystathionine metabolites on superoxide generation in human neutrophils
33. Simple methods for the detection and quantification of thiols from Crithidia fasciculata and for the isolation of trypanothione