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Tetrahydromethanopterin

February 15, 2024

Tetrahydromethanopterin (THMPT, H
4MPT) is a coenzyme in methanogenesis. It is the carrier of the C1 group as it is reduced to the methyl level, before transferring to the coenzyme M.[1]

Tetrahydromethanopterin
Identifiers
  • 92481-94-2 N
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4573696 Y
  • 5462234
  • DTXSID70919150
  • InChI=1S/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 Y
    Key: SCBIBGUJSMHIAI-FDLOOEGASA-N Y
  • 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
    Key: SCBIBGUJSMHIAI-FDLOOEGABF
  • O=C2/N=C(/N)NC=1N[C@@H](C)C(NC=12)[C@H](Nc3ccc(cc3)C[C@H](O)[C@H](O)[C@H](O)CO[C@H]4O[C@@H]([C@@H](O)[C@H]4O)COP(=O)(O[C@H](C(=O)O)CCC(=O)O)O)C
Properties
C
30H
45N
6O
16P
Molar mass 776.682661
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Tetrahydrosarcinapterin (THSPT, H
4SPT) is a modified form of THMPT, wherein a glutamyl group linked to the 2-hydroxyglutaric acid terminus.

THMPT is the main platform for C1 transformations edit

N-Formylmethanofuran donates the C1 group to the N5 site of the pterin to give the formyl- THMPT.[2] The formyl group subsequently condenses intramolecularly to give methenyl- THMPT+
, which is then reduced to methylene- THMPT.[3] Methylene- MPT is subsequently converted, using coenzyme F420 as the electron source, to methyl- THMPT, catalyzed by F420-dependent methylene-THMPT reductase. Methyl- THMPT is the methyl donor to coenzyme M, a conversion mediated by methyl-THMPT:coenzyme M methyltransferase.[1]

Comparison with tetrahydrofolic acid edit

THMPT is related to the better known tetrahydrofolic acid (THFA, H
4FA). 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 iron-sulfur cluster free hydrogenase.[3] The cumbersome name distinguishes this hydrogenase from the so-called Fe-only hydrogenases that do contain Fe-S cluster.

References edit

  1. ^ a b Thauer RK (September 1998). "Biochemistry of methanogenesis: a tribute to Marjory Stephenson. 1998 Marjory Stephenson Prize Lecture". Microbiology. 144 (Pt 9): 2377–406. doi:10.1099/00221287-144-9-2377. PMID 9782487.
  2. ^ Acharya P, Warkentin E, Ermler U, Thauer RK, Shima S (March 2006). "The structure of formylmethanofuran: tetrahydromethanopterin formyltransferase in complex with its coenzymes". J. Mol. Biol. 357 (3): 870–9. doi:10.1016/j.jmb.2006.01.015. PMID 16466742.
  3. ^ a b Korbas M, Vogt S, Meyer-Klaucke W, et al. (October 2006). "The iron-sulfur cluster-free hydrogenase (Hmd) is a metalloenzyme with a novel iron binding motif". J. Biol. Chem. 281 (41): 30804–13. doi:10.1074/jbc.M605306200. PMID 16887798.

February 15, 2024
tetrahydromethanopterin, thmpt, coenzyme, methanogenesis, carrier, group, reduced, methyl, level, before, transferring, coenzyme, identifierscas, number, 92481, model, jsmol, interactive, imagechemspider, 4573696, ypubchem, 5462234comptox, dashboard, dtxsid709. Tetrahydromethanopterin THMPT H4 MPT is a coenzyme in methanogenesis It is the carrier of the C1 group as it is reduced to the methyl level before transferring to the coenzyme M 1 Tetrahydromethanopterin IdentifiersCAS Number 92481 94 2 N3D model JSmol Interactive imageChemSpider 4573696 YPubChem CID 5462234CompTox Dashboard EPA DTXSID70919150InChI InChI 1S 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 YKey SCBIBGUJSMHIAI FDLOOEGASA N YInChI 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 s1Key SCBIBGUJSMHIAI FDLOOEGABFSMILES O C2 N C N NC 1N C H C C NC 12 C H Nc3ccc cc3 C C H O C H O C H O CO C H 4O C H C H O C H 4O COP O O C H C O O CCC O O O CPropertiesChemical formula C30 H45 N6 O16 PMolar mass 776 682661Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Tetrahydrosarcinapterin THSPT H4 SPT is a modified form of THMPT wherein a glutamyl group linked to the 2 hydroxyglutaric acid terminus THMPT is the main platform for C1 transformations editN Formylmethanofuran donates the C1 group to the N5 site of the pterin to give the formyl THMPT 2 The formyl group subsequently condenses intramolecularly to give methenyl THMPT which is then reduced to methylene THMPT 3 Methylene MPT is subsequently converted using coenzyme F420 as the electron source to methyl THMPT catalyzed by F420 dependent methylene THMPT reductase Methyl THMPT is the methyl donor to coenzyme M a conversion mediated by methyl THMPT coenzyme M methyltransferase 1 Comparison with tetrahydrofolic acid editTHMPT is related to the better known tetrahydrofolic acid THFA H4 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 iron sulfur cluster free hydrogenase 3 The cumbersome name distinguishes this hydrogenase from the so called Fe only hydrogenases that do contain Fe S cluster References edit a b Thauer RK September 1998 Biochemistry of methanogenesis a tribute to Marjory Stephenson 1998 Marjory Stephenson Prize Lecture Microbiology 144 Pt 9 2377 406 doi 10 1099 00221287 144 9 2377 PMID 9782487 Acharya P Warkentin E Ermler U Thauer RK Shima S March 2006 The structure of formylmethanofuran tetrahydromethanopterin formyltransferase in complex with its coenzymes J Mol Biol 357 3 870 9 doi 10 1016 j jmb 2006 01 015 PMID 16466742 a b Korbas M Vogt S Meyer Klaucke W et al October 2006 The iron sulfur cluster free hydrogenase Hmd is a metalloenzyme with a novel iron binding motif J Biol Chem 281 41 30804 13 doi 10 1074 jbc M605306200 PMID 16887798 Retrieved from https en wikipedia org w index php title Tetrahydromethanopterin amp oldid 1074200655, wikipedia, wiki, book, books, library,

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