Thiamine monophosphate

Thiamine monophosphate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.762 Edit this at Wikidata
MeSH Thiamine+Monophosphate
UNII
  • 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 checkY
    Key: GUGWNSHJDUEHNJ-UHFFFAOYSA-N checkY
  • 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
  • Cc1c(sc[n+]1Cc2cnc(nc2N)C)CCOP(=O)(O)O.[Cl-]
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).
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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

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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

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  1. ^ Mancinelli R, Ceccanti M, Guiducci MS, Sasso GF, Sebastiani G, Attilia ML, et al. (June 2003). "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. doi:10.1016/S1570-0232(03)00139-9. PMID 12742126.
  2. ^ a b Lonsdale D (2018). "Thiamin". Advances in Food and Nutrition Research. 83. Elsevier: 1–56. doi:10.1016/bs.afnr.2017.11.001. ISBN 978-0-12-811803-0. PMID 29477220.
  3. ^ Lonsdale D, Marrs C (January 2017). "Chapter 3 - Mitochondria, Thiamine, and Autonomic Dysfunction". In Lonsdale D, Marrs C (eds.). Thiamine Deficiency Disease, Dysautonomia, and High Calorie Malnutrition. Academic Press. pp. 59–103. doi:10.1016/b978-0-12-810387-6.00003-4. ISBN 978-0-12-810387-6.
  4. ^ a b c Gangolf M, Czerniecki J, Radermecker M, Detry O, Nisolle M, Jouan C, et al. (October 2010). German M (ed.). "Thiamine status in humans and content of phosphorylated thiamine derivatives in biopsies and cultured cells". PLOS ONE. 5 (10): e13616. Bibcode:2010PLoSO...513616G. doi:10.1371/journal.pone.0013616. PMC 2963613. PMID 21049048.
  5. ^ Burch HB, Bessey OA, Love RH, Lowry OH (September 1952). "The determination of thiamine and thiamine phosphates in small quantities of blood and blood cells". The Journal of Biological Chemistry. 198 (1): 477–490. doi:10.1016/s0021-9258(18)55601-5. PMID 12999762.
  6. ^ Leder IG (November 1961). "The enzymatic synthesis of thiamine monophosphate". The Journal of Biological Chemistry. 236 (11): 3066–3071. doi:10.1016/s0021-9258(19)76430-8. PMID 14463407.
  7. ^ Rindi G, Patrini C, Poloni M (September 1981). "Monophosphate, the only phosphoric ester of thiamin in the cerebro-spinal fluid". Experientia. 37 (9): 975–976. doi:10.1007/BF01971788. PMID 7297660.
  8. ^ Schmidt A, Pratsch H, Schreiner MG, Mayer HK (August 2017). "Determination of the native forms of vitamin B1 in bovine milk using a fast and simplified UHPLC method". Food Chemistry. 229: 452–457. doi:10.1016/j.foodchem.2017.02.092. PMID 28372200.
  9. ^ Rindi G, De Giuseppe L, Sciorelli G (April 1968). "Thiamine monophosphate, a normal constituent of rat plasma". The Journal of Nutrition. 94 (4): 447–454. doi:10.1093/jn/94.4.447. PMID 4297480.
  10. ^ Reggiani C, Patrini C, Rindi G (February 1984). "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. doi:10.1016/0006-8993(84)91239-3. PMID 6697223.
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