Back تیامین مونوفوسفات AZB Tiamina monofosfato Esperanto تیامین مونوفسفات Persian Monophosphate de thiamine French Tiamin monofosfat Serbo-Croatian Tiamin monofosfat Serbian தயமின் மோனோபாசுபேட்டு Tamil

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]

  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. ^ 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.
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