The formation of hydrogen cyanide from histidine in the presence of amino acid oxidase and peroxidase

Gewitz, Hans-Siegfried; Piefke, Jutta; Langowska, K.; Vennesland, Birgit

doi:10.1016/0005-2744(80)90037-6

Cited by 18 publications

(4 citation statements)

References 24 publications

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“…Despite the toxicity of CN -, most pathogenic strains of P. aeruginosa are known to be cyanogenic, producing concentrations of CNin excess of 300 µM during batch cultures. HCN has been detected in the CF lung (55), and it has been assumed that this is evidence of the presence of P. aeruginosa, but we note that HCN is also produced by neutrophils, which are pervasive in the CF lung (56)(57)(58)(59)(60)(61). Accordingly, the origin of HCN in the CF lung remains to be established.…”

Section: Discussionmentioning

confidence: 79%

Reactive Sulfur Species: Kinetics and Mechanism of the Reaction of Hypothiocyanous Acid with Cyanide To Give Dicyanosulfide in Aqueous Solution

Lemma

Ashby

2009

Chem. Res. Toxicol.

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The chief sources of cyanide (CN(-)) in humans are tobacco and occupationally derived smoke, inflammation [vis-a-vis myeloperoxidase (MPO)-induced chlorination of glycine], and microbial cyanogenesis (including Pseudomonas aeruginosa infection of the cystic fibrosis lung). The human mucosae of healthy individuals are usually protected from infection by innate defense mechanisms that include the defensive peroxidase systems. In the oral cavity, salivary peroxidase and MPO catalyze the oxidation of the pseudohalide thiocyanate (SCN(-)) by hydrogen peroxide to produce the antimicrobial hypothiocyanite (OSCN(-)). Lactoperoxidase carries out the same reaction in the human lung (as does MPO during inflammatory response). In the present study, we show that OSCN(-) and CN(-) react with pH-dependent kinetics to produce SCN(-) and cyanate (OCN(-)) via dicyanosulfide (NCSCN), with the maximum rate occurring near neutral, physiological pH. In addition to presenting a detailed chemical mechanism, we discuss unresolved issues, including the possible biological relevance of the NCSCN intermediate.

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Section: Discussionmentioning

confidence: 79%

Reactive Sulfur Species: Kinetics and Mechanism of the Reaction of Hypothiocyanous Acid with Cyanide To Give Dicyanosulfide in Aqueous Solution

Lemma

Ashby

2009

Chem. Res. Toxicol.

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“…HCN production is stimulated mainly from histidine (Pistorius and Voss, 1977) and other aromatic amino acids is a general reaction catalysed by D-amino acid and L-amino acid oxidoreductases. The stoicheiometry of this process was investigated by Gewitz et al (Gewitz et al, 1980) using snake venom L-amino acid oxidase and horseradish. Under optimal conditions, this system converted 72% of the added histidine into cyanide.…”

Section: Cyanogenic Cyanobacteriamentioning

confidence: 99%

Unravelling unknown cyanobacteria diversity linked with HCN production

Panou

Gkelis

2022

Molecular Phylogenetics and Evolution

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“…This identification was confirmed by mass spectrometry analysis (MS and MS/MS), proton NMR and RP HPLC. The only other report in the literature we are aware of is by Gewitz et al (37), who reacted free L-histidine with L-amino acid oxidase and horseradish peroxidase to yield 4(5)-imidazolecarboxaldehyde, 4(5)-imidazolecarboxylic acid, carbon dioxide, ammonia, and hydrogen peroxide. 4(5)-imidazolecarboxaldehyde is commercially available and can be prepared through a variety of synthetic pathways (37)(38)(39)(40)(41)(42)(43)(44)(45)(46)(47)(48)(49), which are different from the oxidation of L-histidine currently being discussed.…”

Section: Discussionmentioning

confidence: 96%