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Thiophosphate


Thiophosphates (or phosphorothioates, PS) are chemical compounds and anions with the general chemical formula PS4−xO3−
x
(x = 0, 1, 2, or 3) and related derivatives where organic groups are attached to one or more O or S. Thiophosphates feature tetrahedral phosphorus(V) centers.

Organothiophosphates are a subclass of organophosphorus compounds that are structurally related to the inorganic thiophosphates. Common members have formulas of the type (RO)3-xRxPS and related compounds where RO is replaced by RS. Many of these compounds are used as insecticides, some have medical applications, and some have been used as oil additives.

Oligonucleotide phosphorothioates (OPS) are modified oligonucleotides where one of the oxygen atoms in the phosphate moiety is replaced by sulfur. They are the basis of antisense therapy, e.g., the drugs fomivirsen (Vitravene), oblimersen, alicaforsen, and mipomersen (Kynamro).

The simplest thiophosphates have the formula [PS4−xOx]3−. These trianions are only observed at very high pH, instead they exist in protonated form with the formul [HnPS4−xOx](3-n)-.

Monothiophosphate is the anion [PO3S]3−, which has C3vsymmetry. A common salt is sodium monothiophosphate (Na3PO3S). Monothiophosphate is used in research as an analogue of phosphate in biochemistry. Monothiophosphate esters are biochemical reagents used in the study of transcription, substitution interference assays. Sometimes," monothiophosphate" refers to esters such as (CH3O)2POS.


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