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Hypothiocyanite

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Hypothiocyanite

Hypothiocyanite is the anion [OSCN] and the conjugate base of hypothiocyanous acid (HOSCN). It is an organic compound part of the thiocyanates as it contains the functional group SCN. It is formed when an oxygen is singly bonded to the thiocyanate group. Hypothiocyanous acid is a fairly weak acid; its acid dissociation constant (pKa) is 5.3.

Hypothiocyanite is formed by peroxidase catalysis of hydrogen peroxide and thiocyanate:

Hypothiocyanite occurs naturally in the antimicrobial immune system of the human respiratory tract in a redox reaction catalyzed by the enzyme lactoperoxidase. It has been researched extensively for its capabilities as an alternative antibiotic as it is harmless to human body cells while being cytotoxic to bacteria. The exact processes for making hypothiocyanite have been patented as such an effective antimicrobial has many commercial applications.

Lactoperoxidase-catalysed reactions yield short-lived intermediary oxidation products of SCN, providing antibacterial activity.

The major intermediary oxidation product is hypothiocyanite OSCN, which is produced in an amount of about 1 mole per mole of hydrogen peroxide. At the pH optimum of 5.3, the OSCN is in equilibrium with HOSCN. The uncharged HOSCN is considered to be the greater bactericidal of the two forms. At pH 7, it was evaluated that HOSCN represents 2% compare to OSCN 98%.

The action of OSCN against bacteria is reported to be caused by sulfhydryl (SH) oxidation.

The oxidation of -SH groups in the bacterial cytoplasmic membrane results in loss of the ability to transport glucose and also in leaking of potassium ions, amino acids and peptide.

OSCN has also been identified as an antimicrobial agent in milk, saliva, tears, and mucus.

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