| Revision as of 16:46, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,054 edits Saving copy of the {{chembox}} taken from revid 437930415 of page 10-Formyltetrahydrofolate for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 17:07, 31 July 2023 edit 192.234.172.230 (talk)No edit summary |
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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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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 399191626 |
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| verifiedrevid = 477208698 |
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|ImageFile=10-formyl-tetrahydrofolic acid.svg |
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| ImageFile=10-formyl-tetrahydrofolic acid.svg |
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|ImageSize= |
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| ImageSize=260 |
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| ImageAlt = Skeletal formula of 10-formyltetrahydrofolate |
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|IUPACName=(2''S'')-2-{benzoyl]amino}pentanedioic acid |
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| ImageFile1 = 10-Formyltetrahydrofolate-3D-spacefill.png |
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|OtherNames= 10-CHO-THF |
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| ImageSize1 = 250 |
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|Section1= {{Chembox Identifiers |
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| ImageAlt1 = Space-filling model of the 10-formyltetrahydrofolate molecule |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PIN=(2''S'')-2-methyl}formamido)benzamido]pentanedioic acid |
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| ChemSpiderID = 9 |
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| OtherNames= {{ubl|10-CHO-THF|10-FormylH<sub>4</sub>folate|''N''<sup>10</sup>-Formyltetrahydrofolate}} |
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| InChI = 1/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32) |
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|Section1={{Chembox Identifiers |
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| InChIKey = AUFGTPPARQZWDO-UHFFFAOYAK |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| SMILES1 = O=C(O)C(NC(=O)c1ccc(cc1)N(C=O)CC3N/C2=C(/N/C(=N\C2=O)N)NC3)CCC(=O)O |
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| ChemSpiderID = 109092 |
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| SMILES = c1cc(ccc1C(=O)N(CCC(=O)O)C(=O)O)N(CC2CNc3c(c(=O)nc(3)N)N2)C=O |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32) |
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| StdInChI = 1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11?,13-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = AUFGTPPARQZWDO-UHFFFAOYSA-N |
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| StdInChIKey = AUFGTPPARQZWDO-YUZLPWPTSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 2800-34-2 --> |
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| CASNo=2800-34-2 |
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| PubChem=10 |
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| PubChem=135450591 |
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| SMILES=C1C(NC2=C(N1)NC(=NC2=O)N)CN(C=O)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O |
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| KEGG=C00234 |
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| MeSHName=10-formyl-tetrahydrofolate |
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| MeSHName=10-formyl-tetrahydrofolate |
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}} |
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}} |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>20</sub>H<sub>23</sub>N<sub>7</sub>O<sub>7</sub> |
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| Formula=C<sub>20</sub>H<sub>23</sub>N<sub>7</sub>O<sub>7</sub> |
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| MolarMass=473.44 g/mol |
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| MolarMass=473.44 g/mol |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''10-Formyltetrahydrofolate''' ('''10-CHO-THF''') is a form of ] that acts as a donor of ]s in ]. In these reactions 10-CHO-THF is used as a ] in formyltransferase reactions. |
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==Functions== |
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Two equivalents of 10-CHO-THF are required in ] through the ], where 10-CHO-THF is a substrate for ]. |
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10-CHO-THF is required for the formylation of ] to give ]-tRNA.<ref>{{cite book|last1=Voet|first1=Donald|title=Fundamentals of Biochemistry: Life at the Molecular Level|date=2016|publisher=Wiley|isbn=978-1-118-91840-1|pages=1006–1007|edition=5th}}</ref> |
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==Formation from methenyltetrahydrofolate== |
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10-CHO-THF is produced from ] (CH<sub>2</sub>H<sub>4</sub>F) via a two step process. The first step generates ]:<ref>{{cite journal|title=Methenyltetrahydrofolate Cyclohydrolase Is Rate Limiting for the Enzymatic Conversion of 10-Formyltetrahydrofolate to 5,10-Methylenetetrahydrofolate in Bifunctional Dehydrogenase-Cyclohydrolase Enzymes|author1=Peter D. Pawelek |author2=Robert E. MacKenzie|journal=Biochemistry|year=1998|volume=37|issue=4 |pages=1109–1115|doi=10.1021/bi971906t|pmid=9454603}}</ref> |
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:CH<sub>2</sub>H<sub>4</sub>F + NAD<sup>+</sup> <math>\rightleftharpoons</math> CH<sub>2</sub>H<sub>2</sub>F + NADH + H<sup>+</sup> |
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In the second step 5,10-methenyltetrahydrofolate undergoes hydrolysis: |
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:CH<sub>2</sub>H<sub>2</sub>F + H<sub>2</sub>O <math>\rightleftharpoons</math> CHO-H<sub>4</sub>F + |
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The latter is equivalently written: |
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:] + H<sub>2</sub>O <math>\rightleftharpoons</math> 10-formyltetrahydrofolate |
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10-CHO-THF is also produced by the reaction |
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:ATP + ] + tetrahydrofolate <math>\rightleftharpoons</math> ADP + phosphate + 10-formyltetrahydrofolate |
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This reaction is catalyzed by ]. |
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It can be converted back into ] (THF) by ] or THF and formate by ]. |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Formyl-tetrahydrofolate, 10-}} |
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] |
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] |