Tetrahydromethanopterin

From Wikipedia, the free encyclopedia
(Redirected from Methanopterin)
Jump to navigation Jump to search
Tetrahydromethanopterin
File:Tetrahydromethanopterin.svg
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • 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 checkY
    Key: SCBIBGUJSMHIAI-FDLOOEGASA-N checkY
  • 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).

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]

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 | edit source]

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 by 5,10-methenyl-THMPT+
 hydrogenase with H
2 as the electron donor.[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 | edit source]

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.[citation needed]

References

[edit | edit source]
  1. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  3. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
Retrieved from "http://70.231.62.181/index.php?title=Tetrahydromethanopterin&oldid=5579288"