Thiamine monophosphate

Thiamine monophosphate
Identifiers
CAS Number	10023-48-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9533 ;
ChemSpider	10307 ;
MeSH	Thiamine+Monophosphate
PubChem CID	10761;
UNII	71F2V60NN0 ;
	InChI InChI=1S/C12H17N4O4PS.ClH/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13;/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19);1H Key: GUGWNSHJDUEHNJ-UHFFFAOYSA-N ; InChI=1/C12H17N4O4PS.ClH/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13;/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19);1H Key: GUGWNSHJDUEHNJ-UHFFFAOYAK;
	SMILES Cc1c(sc[n+]1Cc2cnc(nc2N)C)CCOP(=O)(O)O.[Cl-];
Properties
Chemical formula	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).
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	Infobox references

Thiamine monophosphate, also known as ThMP and TMP, is a phosphate ester of thiamine.^[1]

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]

References

↑ "Simultaneous liquid chromatographic assessment of thiamine, thiamine monophosphate and thiamine diphosphate in human erythrocytes: a study on alcoholics". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 789 (2): 355–363. June 2003. doi:10.1016/S1570-0232(03)00139-9. PMID 12742126.
↑ ^2.0 ^2.1 "Thiamin". Advances in Food and Nutrition Research (Elsevier) 83: 1–56. 2018. doi:10.1016/bs.afnr.2017.11.001. ISBN 978-0-12-811803-0. PMID 29477220.
↑ "Chapter 3 - Mitochondria, Thiamine, and Autonomic Dysfunction". Thiamine Deficiency Disease, Dysautonomia, and High Calorie Malnutrition. Academic Press. January 2017. pp. 59–103. doi:10.1016/b978-0-12-810387-6.00003-4. ISBN 978-0-12-810387-6.
↑ ^4.0 ^4.1 ^4.2 "Thiamine status in humans and content of phosphorylated thiamine derivatives in biopsies and cultured cells". PLOS ONE 5 (10). October 2010. doi:10.1371/journal.pone.0013616. PMID 21049048. Bibcode: 2010PLoSO...513616G.
↑ "The determination of thiamine and thiamine phosphates in small quantities of blood and blood cells". The Journal of Biological Chemistry 198 (1): 477–490. September 1952. doi:10.1016/s0021-9258(18)55601-5. PMID 12999762.
↑ "The enzymatic synthesis of thiamine monophosphate". The Journal of Biological Chemistry 236 (11): 3066–3071. November 1961. doi:10.1016/s0021-9258(19)76430-8. PMID 14463407.
↑ "Monophosphate, the only phosphoric ester of thiamin in the cerebro-spinal fluid". Experientia 37 (9): 975–976. September 1981. doi:10.1007/BF01971788. PMID 7297660.
↑ "Determination of the native forms of vitamin B₁ in bovine milk using a fast and simplified UHPLC method". Food Chemistry 229: 452–457. August 2017. doi:10.1016/j.foodchem.2017.02.092. PMID 28372200.
↑ "Thiamine monophosphate, a normal constituent of rat plasma". The Journal of Nutrition 94 (4): 447–454. April 1968. doi:10.1093/jn/94.4.447. PMID 4297480.
↑ "Nervous tissue thiamine metabolism in vivo. I. Transport of thiamine and thiamine monophosphate from plasma to different brain regions of the rat". Brain Research 293 (2): 319–327. February 1984. doi:10.1016/0006-8993(84)91239-3. PMID 6697223.

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[1] "Simultaneous liquid chromatographic assessment of thiamine, thiamine monophosphate and thiamine diphosphate in human erythrocytes: a study on alcoholics". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 789 (2): 355–363. June 2003. doi:10.1016/S1570-0232(03)00139-9. PMID 12742126.

[:0-2] 2.0 ^2.1 "Thiamin". Advances in Food and Nutrition Research (Elsevier) 83: 1–56. 2018. doi:10.1016/bs.afnr.2017.11.001. ISBN 978-0-12-811803-0. PMID 29477220.

[3] "Chapter 3 - Mitochondria, Thiamine, and Autonomic Dysfunction". Thiamine Deficiency Disease, Dysautonomia, and High Calorie Malnutrition. Academic Press. January 2017. pp. 59–103. doi:10.1016/b978-0-12-810387-6.00003-4. ISBN 978-0-12-810387-6.

[:1-4] 4.0 ^4.1 ^4.2 "Thiamine status in humans and content of phosphorylated thiamine derivatives in biopsies and cultured cells". PLOS ONE 5 (10). October 2010. doi:10.1371/journal.pone.0013616. PMID 21049048. Bibcode: 2010PLoSO...513616G.

[5] "The determination of thiamine and thiamine phosphates in small quantities of blood and blood cells". The Journal of Biological Chemistry 198 (1): 477–490. September 1952. doi:10.1016/s0021-9258(18)55601-5. PMID 12999762.

[6] "The enzymatic synthesis of thiamine monophosphate". The Journal of Biological Chemistry 236 (11): 3066–3071. November 1961. doi:10.1016/s0021-9258(19)76430-8. PMID 14463407.

[7] "Monophosphate, the only phosphoric ester of thiamin in the cerebro-spinal fluid". Experientia 37 (9): 975–976. September 1981. doi:10.1007/BF01971788. PMID 7297660.

[8] "Determination of the native forms of vitamin B₁ in bovine milk using a fast and simplified UHPLC method". Food Chemistry 229: 452–457. August 2017. doi:10.1016/j.foodchem.2017.02.092. PMID 28372200.

[9] "Thiamine monophosphate, a normal constituent of rat plasma". The Journal of Nutrition 94 (4): 447–454. April 1968. doi:10.1093/jn/94.4.447. PMID 4297480.

[10] "Nervous tissue thiamine metabolism in vivo. I. Transport of thiamine and thiamine monophosphate from plasma to different brain regions of the rat". Brain Research 293 (2): 319–327. February 1984. doi:10.1016/0006-8993(84)91239-3. PMID 6697223.

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Identifiers

CAS Number	10023-48-0^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9533^Y
ChemSpider	10307^Y
MeSH	Thiamine+Monophosphate
PubChem CID	10761
UNII	71F2V60NN0^Y
InChI InChI=1S/C12H17N4O4PS.ClH/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13;/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19);1H^Y Key: GUGWNSHJDUEHNJ-UHFFFAOYSA-N^Y InChI=1/C12H17N4O4PS.ClH/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13;/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19);1H Key: GUGWNSHJDUEHNJ-UHFFFAOYAK
SMILES Cc1c(sc[n+]1Cc2cnc(nc2N)C)CCOP(=O)(O)O.[Cl-]
Properties
Chemical formula	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).
N verify (what is ^YN ?)
Infobox references

Thiamine monophosphate

Topic: Chemistry

Physiological presence

References