| Revision as of 12:40, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 462319316 of page Tetrahydromethanopterin for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 00:23, 27 February 2022 edit Teaktl17 (talk | contribs)Extended confirmed users17,957 editsm →Comparison with tetrahydrofolic acid: +wl |
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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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| verifiedrevid = 425799155 |
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| verifiedrevid = 470604354 |
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|ImageFile=Tetrahydromethanopterin.svg |
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| ImageFile=Tetrahydromethanopterin.svg |
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|ImageSize=350px |
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| ImageSize=350px |
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|IUPACName= |
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|OtherNames= |
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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 = 4573696 |
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| ChemSpiderID = 4573696 |
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| InChI = 1/C30H45N6O16P/c1-12(21-13(2)33-26-22(34-21)27(44)36-30(31)35-26)32-15-5-3-14(4-6-15)9-16(37)23(41)17(38)10-49-29-25(43)24(42)19(51-29)11-50-53(47,48)52-18(28(45)46)7-8-20(39)40/h3-6,12-13,16-19,21,23-25,29,32,34,37-38,41-43H,7-11H2,1-2H3,(H,39,40)(H,45,46)(H,47,48)(H4,31,33,35,36,44)/t12-,13+,16+,17-,18+,19-,21?,23+,24-,25-,29+/m1/s1 |
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| InChI = 1/C30H45N6O16P/c1-12(21-13(2)33-26-22(34-21)27(44)36-30(31)35-26)32-15-5-3-14(4-6-15)9-16(37)23(41)17(38)10-49-29-25(43)24(42)19(51-29)11-50-53(47,48)52-18(28(45)46)7-8-20(39)40/h3-6,12-13,16-19,21,23-25,29,32,34,37-38,41-43H,7-11H2,1-2H3,(H,39,40)(H,45,46)(H,47,48)(H4,31,33,35,36,44)/t12-,13+,16+,17-,18+,19-,21?,23+,24-,25-,29+/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = SCBIBGUJSMHIAI-FDLOOEGASA-N |
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| StdInChIKey = SCBIBGUJSMHIAI-FDLOOEGASA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo= |
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| CASNo= 92481-94-2 |
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| PubChem=5459995 |
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| PubChem=5462234 |
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| SMILES = O=C2/N=C(/N)NC=1N(C)C(NC=12)(Nc3ccc(cc3)C(O)(O)(O)CO4O((O)4O)COP(=O)(O(C(=O)O)CCC(=O)O)O)C |
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| SMILES = O=C2/N=C(/N)NC=1N(C)C(NC=12)(Nc3ccc(cc3)C(O)(O)(O)CO4O((O)4O)COP(=O)(O(C(=O)O)CCC(=O)O)O)C |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula={{chem|C|30|H|45|N|6|O|16|P}} |
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| Formula={{chem|C|30|H|45|N|6|O|16|P}} |
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| MolarMass=776.682661 |
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| MolarMass=776.682661 |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''Tetrahydromethanopterin''' ('''THMPT''', '''{{chem|H|4|MPT}}''') is a ] in ]. It is the carrier of the C1 group as it is reduced to the ] level, before transferring to the ].<ref name=Thauer>{{cite journal |author=Thauer RK |title=Biochemistry of methanogenesis: a tribute to Marjory Stephenson. 1998 Marjory Stephenson Prize Lecture |journal=Microbiology |volume=144 |issue=Pt 9 |pages=2377–406 |date=September 1998 |pmid=9782487 |url=http://mic.sgmjournals.org/cgi/pmidlookup?view=long&pmid=9782487 |doi=10.1099/00221287-144-9-2377|doi-access=free }}</ref> |
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] (THSPT, {{chem|H|4|SPT}}) is a modified form of THMPT, wherein a ] group linked to the 2-hydroxy] terminus. |
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== THMPT is the main platform for C1 transformations == |
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N-Formyl] donates the C1 group to the N5 site of the ] to give the formyl- THMPT.<ref>{{cite journal |vauthors=Acharya P, Warkentin E, Ermler U, Thauer RK, Shima S |title=The structure of formylmethanofuran: tetrahydromethanopterin formyltransferase in complex with its coenzymes |journal=J. Mol. Biol. |volume=357 |issue=3 |pages=870–9 |date=March 2006 |pmid=16466742 |doi=10.1016/j.jmb.2006.01.015 }}</ref> The formyl group subsequently condenses intramolecularly to give methenyl- {{chem|THMPT|+}}, which is then reduced to methylene- THMPT.<ref name=Korbas>{{cite journal |vauthors=Korbas M, Vogt S, Meyer-Klaucke W, etal |title=The iron-sulfur cluster-free hydrogenase (Hmd) is a metalloenzyme with a novel iron binding motif |journal=J. Biol. Chem. |volume=281 |issue=41 |pages=30804–13 |date=October 2006 |pmid=16887798 |doi=10.1074/jbc.M605306200 |doi-access=free }}</ref> Methylene- MPT is subsequently converted, using ] as the electron source, to methyl- THMPT, catalyzed by ]. Methyl- THMPT is the ] donor to ], a conversion mediated by ].<ref name=Thauer/> |
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== Comparison with tetrahydrofolic acid == |
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THMPT is related to the better known ] (THFA, {{chem|H|4|FA}}). The most important difference between THMPT and THFA is that THFA has an electron-withdrawing carbonyl group on the phenyl ring. As a consequence, methenyl- THMPT is more difficult to reduce than methenyl- THFA. Reduction is effected by a so-called ].<ref name=Korbas/> The cumbersome name distinguishes this hydrogenase from the so-called Fe-only ]s that do contain ]. |
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== References == |
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{{reflist}} |
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{{Enzyme cofactors}} |
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