| Revision as of 12:56, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 444225047 of page Thiamine_monophosphate for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 16:31, 20 May 2024 edit Marbletan (talk | contribs)Extended confirmed users5,350 edits no longer a stub |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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| verifiedrevid = 444224074 |
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| verifiedrevid = 470606219 |
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|ImageFile=Thiamine monophosphate.svg |
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| ImageFile=Thiamine monophosphate.svg |
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|ImageSize=250px |
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| ImageSize=250px |
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|IUPACName= |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10307 |
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| ChemSpiderID = 10307 |
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| 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 |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = GUGWNSHJDUEHNJ-UHFFFAOYSA-N |
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| StdInChIKey = GUGWNSHJDUEHNJ-UHFFFAOYSA-N |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo = <!-- blanked - oldvalue: 532-40-1 --> |
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| PubChem = 10761 |
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| UNII = 71F2V60NN0 |
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| CASNo= 10023-48-0 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| ChEBI = 18338 |
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| PubChem = 10761 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 9533 |
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| SMILES = Cc1c(sc1Cc2cnc(nc2N)C)CCOP(=O)(O)O. |
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| SMILES = Cc1c(sc1Cc2cnc(nc2N)C)CCOP(=O)(O)O. |
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| MeSHName=Thiamine+Monophosphate |
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| MeSHName=Thiamine+Monophosphate |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>12</sub>H<sub>18</sub>N<sub>4</sub>O<sub>4</sub>PS+ |
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| Formula=C<sub>12</sub>H<sub>18</sub>N<sub>4</sub>O<sub>4</sub>PS+ |
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| MolarMass=345.336 g/mol |
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| MolarMass=345.336 g/mol |
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'''Thiamine monophosphate,''' also known as ThMP and TMP, is a ] of ].<ref>{{cite journal | vauthors = Mancinelli R, Ceccanti M, Guiducci MS, Sasso GF, Sebastiani G, Attilia ML, Allen JP | title = Simultaneous liquid chromatographic assessment of thiamine, thiamine monophosphate and thiamine diphosphate in human erythrocytes: a study on alcoholics | journal = Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences | volume = 789 | issue = 2 | pages = 355–363 | date = June 2003 | pmid = 12742126 | doi = 10.1016/S1570-0232(03)00139-9 }}</ref> |
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It is an intermediate from the hydrolysis of ] to free thiamine by ].<ref name=":0">{{cite journal | vauthors = Lonsdale D | title = Thiamin | journal = Advances in Food and Nutrition Research | volume = 83 | pages = 1–56 | date = 2018 | pmid = 29477220 | doi = 10.1016/bs.afnr.2017.11.001 | publisher = Elsevier | isbn = 978-0-12-811803-0 }}</ref><ref>{{cite book | vauthors = Lonsdale D, Marrs C | chapter = Chapter 3 - Mitochondria, Thiamine, and Autonomic Dysfunction |date= January 2017 | veditors = Lonsdale D, Marrs C | title = Thiamine Deficiency Disease, Dysautonomia, and High Calorie Malnutrition |pages=59–103 |publisher=Academic Press |doi=10.1016/b978-0-12-810387-6.00003-4 |isbn=978-0-12-810387-6 }}</ref><ref name=":1">{{cite journal | vauthors = Gangolf M, Czerniecki J, Radermecker M, Detry O, Nisolle M, Jouan C, Martin D, Chantraine F, Lakaye B, Wins P, Grisar T, Bettendorff L | title = Thiamine status in humans and content of phosphorylated thiamine derivatives in biopsies and cultured cells | journal = PLOS ONE | volume = 5 | issue = 10 | pages = e13616 | date = October 2010 | pmid = 21049048 | pmc = 2963613 | doi = 10.1371/journal.pone.0013616 | doi-access = free | bibcode = 2010PLoSO...513616G | veditors = German M }}</ref> The conversion of ThMP to thiamine cannot be facilitated by acid hydrolysis.<ref>{{cite journal | vauthors = Burch HB, Bessey OA, Love RH, Lowry OH | title = The determination of thiamine and thiamine phosphates in small quantities of blood and blood cells | journal = The Journal of Biological Chemistry | volume = 198 | issue = 1 | pages = 477–490 | date = September 1952 | pmid = 12999762 | doi = 10.1016/s0021-9258(18)55601-5 | doi-access = free }}</ref> ThMP is also enzymatically synthesized by ], which combines thiazole in its monophosphate form and pyrimidine as a pyrophosphate.<ref>{{cite journal | vauthors = Leder IG | title = The enzymatic synthesis of thiamine monophosphate | journal = The Journal of Biological Chemistry | volume = 236 | issue = 11 | pages = 3066–3071 | date = November 1961 | pmid = 14463407 | doi = 10.1016/s0021-9258(19)76430-8 | doi-access = free }}</ref> |
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The physiological function of ThMP has not been identified.<ref name=":0" /> |
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== 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.<ref name=":1" /> ThMP is the only phosphorylated thiamine derivative found in human cerebral spinal fluid.<ref name=":1" /><ref>{{cite journal | vauthors = Rindi G, Patrini C, Poloni M | title = Monophosphate, the only phosphoric ester of thiamin in the cerebro-spinal fluid | journal = Experientia | volume = 37 | issue = 9 | pages = 975–976 | date = September 1981 | pmid = 7297660 | doi = 10.1007/BF01971788 }}</ref> |
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It occurs naturally in bovine milk.<ref>{{cite journal | vauthors = Schmidt A, Pratsch H, Schreiner MG, Mayer HK | title = Determination of the native forms of vitamin B<sub>1</sub> in bovine milk using a fast and simplified UHPLC method | journal = Food Chemistry | volume = 229 | pages = 452–457 | date = August 2017 | pmid = 28372200 | doi = 10.1016/j.foodchem.2017.02.092 }}</ref> |
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In rats, approximately 64% of the total thiamine in plasma exists in its the monophosphate form.<ref>{{cite journal | vauthors = Rindi G, De Giuseppe L, Sciorelli G | title = Thiamine monophosphate, a normal constituent of rat plasma | journal = The Journal of Nutrition | volume = 94 | issue = 4 | pages = 447–454 | date = April 1968 | pmid = 4297480 | doi = 10.1093/jn/94.4.447 }}</ref> 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.<ref>{{cite journal | vauthors = Reggiani C, Patrini C, Rindi G | title = Nervous tissue thiamine metabolism in vivo. I. Transport of thiamine and thiamine monophosphate from plasma to different brain regions of the rat | journal = Brain Research | volume = 293 | issue = 2 | pages = 319–327 | date = February 1984 | pmid = 6697223 | doi = 10.1016/0006-8993(84)91239-3 }}</ref> |
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== References == |
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