Thiamine monophosphate
Chemical compound
From Wikipedia, the free encyclopedia
Thiamine monophosphate, also known as ThMP and TMP, is a phosphate ester of thiamine.[1]
| |
| Identifiers | |
|---|---|
3D model (JSmol) |
|
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.762 |
| MeSH | Thiamine+Monophosphate |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C12H18N4O4PS+ | |
| Molar mass | 345.336 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
It is an intermediate from the hydrolysis of thiamine diphosphate to free thiamine by alkaline phosphatase.[2][3][4] The conversion of ThMP to thiamine cannot be facilitated by acid hydrolysis.[5] ThMP is also enzymatically synthesized by thiamine-phosphate pyrophosphorylase, which combines thiazole in its monophosphate form and pyrimidine as a pyrophosphate.[6]
The physiological function of ThMP has not been identified.[2]
Physiological presence
In whole human blood, both ThMP and free thiamine are present in lower concentrations as compared to TPP, but they are found in low amounts in plasma.[4] ThMP is the only phosphorylated thiamine derivative found in human cerebral spinal fluid.[4][7]
It occurs naturally in bovine milk.[8]
In rats, approximately 64% of the total thiamine in plasma exists in its the monophosphate form.[9] After injection of ThMP into the femoral vein of rats, it was quickly transported to the cerebral tissue without chemical modification, but the average transport rate was 5-10 times slower than that of thiamine.[10]