| Revision as of 15:06, 28 May 2011 editZéroBot (talk | contribs)704,777 editsm r2.7.1) (robot Adding: fr:Xanthosine monophosphate← Previous edit |
Latest revision as of 02:45, 7 November 2023 edit undoCrafterNova (talk | contribs)Extended confirmed users16,642 edits MOS:BOLDTag: 2017 wikitext editor |
| (40 intermediate revisions by 31 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
|
| Watchedfields = changed |
|
| Watchedfields = changed |
|
| verifiedrevid = 384066761 |
|
| verifiedrevid = 431343075 |
|
|ImageFile=Xanthosine monophosphate.svg |
|
| ImageFile=Xanthosine monophosphate.svg |
|
|ImageSize= |
|
| ImageSize= |
|
|IUPACName= 5'-xanthylic acid |
|
| IUPACName= 5'-xanthylic acid |
|
|OtherNames= xanthine ribotide,<br>XMP |
|
| OtherNames= xanthine ribotide,<br>XMP |
|
|Section1= {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
|
| CASNo_Ref = {{cascite|correct|??}} |
|
| CASNo=523-98-8 |
|
| CASNo=523-98-8 |
| ⚫ |
| PubChem=122280 |
|
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| SMILES= |
|
|
|
| UNII = Y29K672ETF |
| ⚫ |
| MeSHName=Xanthosine+monophosphate |
|
|
⚫ |
| PubChem=122280 |
|
⚫ |
| MeSHName=Xanthosine+monophosphate |
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
|
| ChemSpiderID = 66054 |
|
|
| SMILES = C1=NC2=C(N13(((O3)COP(=O)(O)O)O)O)NC(=O)NC2=O |
|
|
| InChI = 1/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1 |
|
|
| InChIKey = DCTLYFZHFGENCW-UUOKFMHZBH |
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChI = 1S/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1 |
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChIKey = DCTLYFZHFGENCW-UUOKFMHZSA-N |
|
|
| RTECS = |
|
|
| ChEBI_Ref = {{ebicite|changed|EBI}} |
|
|
| ChEBI = 15652 |
|
|
| KEGG_Ref = {{keggcite|changed|kegg}} |
|
|
| KEGG = C00655 |
|
}} |
|
}} |
|
|Section2= {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| Formula=C<sub>10</sub>H<sub>13</sub>N<sub>4</sub>O<sub>9</sub>P |
|
| Formula=C<sub>10</sub>H<sub>13</sub>N<sub>4</sub>O<sub>9</sub>P |
|
| MolarMass=364.206 g/mol |
|
| MolarMass=364.206 g/mol |
|
| Appearance= |
|
| Appearance= |
|
| Density= |
|
| Density= |
|
| MeltingPt= |
|
| MeltingPt= |
|
| BoilingPt= |
|
| BoilingPt= |
|
| Solubility= |
|
| Solubility= |
|
}} |
|
}} |
|
|Section3= {{Chembox Hazards |
|
|Section3={{Chembox Hazards |
|
| MainHazards= |
|
| MainHazards= |
|
| FlashPt= |
|
| FlashPt= |
|
|
| AutoignitionPt = |
|
| Autoignition= |
|
|
}} |
|
}} |
|
}} |
|
}} |
|
'''Xanthosine monophosphate''' is an intermediate in ]. It is a ]. It is formed from ] via the action of ], and it forms ] via the action of ]. |
|
'''Xanthosine monophosphate''' ('''xanthylate''') is an intermediate in ].<ref name="McMurry2007">{{cite book|last=McMurry|first=John|title=Organic chemistry: a biological approach|url=https://books.google.com/books?id=mAxLryTHDZkC&pg=PA1007|access-date=26 March 2012|year=2007|publisher=Cengage Learning|isbn=9780495015253|pages=1007–}}</ref> It is a ]. It is formed from ] via the action of ], and it forms ] via the action of ]. Also, XMP can be released from ] by enzyme deoxyribonucleoside triphosphate pyrophosphohydrolase containing (d)XTPase activity.<ref name="pmid 22531138">{{cite journal |vauthors=Davies O, Mendes P, Smallbone K, Malys N | title = Characterisation of multiple substrate-specific (d)ITP/(d)XTPase and modelling of deaminated purine nucleotide metabolism | journal = BMB Reports | volume = 45 | issue = 4 | pages = 259–64 | year = 2012 | pmid = 22531138| doi = 10.5483/BMBRep.2012.45.4.259| url = http://eprints.maths.manchester.ac.uk/1703/1/davies.pdf | doi-access = free }}</ref> |
|
|
|
|
|
|
It is abbreviated XMP.<ref name="Gogia-2011">{{Cite journal | last1 = Gogia | first1 = S. | last2 = Balaram | first2 = H. | last3 = Puranik | first3 = M. | title = Hypoxanthine guanine phosphoribosyltransferase distorts the purine ring of nucleotide substrates and perturbs the pKa of bound xanthosine monophosphate. | journal = Biochemistry | volume = 50 | issue = 19 | pages = 4184–93 |date=May 2011 | doi = 10.1021/bi102039b | pmid = 21486037 }}</ref> |
|
==Clinical significance== |
|
|
Xanthylic acid can be used in quantitative measurements of the ] enzyme activities in purine metabolism, as recommended to ensure optimal ] therapy for children with ] (ALL).<ref name="pmid16725387">{{cite journal |author=Khalil PN, Erb N, Khalil MN, Escherich G, Janka-Schaub GE |title=Validation and application of a high-performance liquid chromatographic-based assay for determination of the inosine 5'-monophosphate dehydrogenase activity in erythrocytes |journal=J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. |volume=842 |issue=1 |pages=1–7 |year=2006 |month=September |pmid=16725387 |doi=10.1016/j.jchromb.2006.04.040 |url=http://linkinghub.elsevier.com/retrieve/pii/S1570-0232(06)00373-4}}</ref> |
|
|
|
|
|
|
==See also== |
|
==See also== |
|
|
|
|
* ] |
|
|
* ] |
|
* ] |
|
|
|
|
|
==References== |
|
==References== |
|
{{reflist}} |
|
{{Reflist}} |
|
|
|
|
|
|
==Further reading== |
|
|
*{{cite journal|pmid=19623361|year=2009|last1=Sigel|first1=H|last2=Operschall|first2=BP|last3=Griesser|first3=R|title=Xanthosine 5'-monophosphate (XMP). Acid-base and metal ion-binding properties of a chameleon-like nucleotide|volume=38|issue=8|pages=2465–94|doi=10.1039/b902181g|journal=Chemical Society Reviews|s2cid=205726340 |url=http://pdfs.semanticscholar.org/e8ab/b310691cc11a918c7769e0d38e42232ad5b6.pdf|archive-url=https://web.archive.org/web/20200101060055/http://pdfs.semanticscholar.org/e8ab/b310691cc11a918c7769e0d38e42232ad5b6.pdf|url-status=dead|archive-date=2020-01-01}} |
|
|
*{{cite journal|pmid=20087997|year=2010|last1=Egli|first1=M|last2=Pallan|first2=PS|title=Crystallographic studies of chemically modified nucleic acids: A backward glance|volume=7|issue=1|pages=60–89|doi=10.1002/cbdv.200900177|pmc=2905155|journal=Chemistry & Biodiversity}} |
|
|
|
|
|
{{Nucleobases, nucleosides, and nucleotides}} |
|
{{Nucleotide metabolism intermediates}} |
|
{{Nucleotide metabolism intermediates}} |
|
|
|
|
|
] |
|
] |
|
] |
|
] |
|
|
|
|
|
|
|
| ⚫ |
{{biochem-stub}} |
|
|
|
|
|
|
⚫ |
{{Biochem-stub}} |
|
] |
|
|
] |
|
|
] |
|