Dihydrosirohydrochlorin

Dihydrosirohydrochlorin
Names
Other names
precorrin 2
Identifiers
CAS Number
  • 82542-92-5 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:50602
ChemSpider
  • 26333172
KEGG
  • C02463
MeSH 15,23-dihydrosirohydrochlorin
PubChem CID
  • 5280516
InChI
  • InChI=1S/C42H48N4O16/c1-41(17-39(59)60)23(5-9-35(51)52)29-14-27-21(11-37(55)56)19(3-7-33(47)48)25(43-27)13-26-20(4-8-34(49)50)22(12-38(57)58)28(44-26)15-31-42(2,18-40(61)62)24(6-10-36(53)54)30(46-31)16-32(41)45-29/h14-16,23-24,43-44,46H,3-13,17-18H2,1-2H3,(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)(H,61,62)/b29-14-,30-16-,31-15-/t23-,24-,41+,42+/m1/s1
    Key: CSWLXNNNLVVXKD-ZIBVGKFXSA-N
  • CC1(C(C2=CC3=NC(=CC4=C(C(=C(N4)CC5=C(C(=C(N5)C=C1N2)CC(=O)O)CCC(=O)O)CCC(=O)O)CC(=O)O)C(C3(C)CC(=O)O)CCC(=O)O)CCC(=O)O)CC(=O)O
Properties
Chemical formula
 C42H48N4O16
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Dihydrosirohydrochlorin is one of several naturally occurring tetrapyrrole macrocyclic metabolic intermediates in the biosynthesis of vitamin B12 (cobalamin). Its oxidised form, sirohydrochlorin, is precursor to sirohaem, the iron-containing prosthetic group in sulfite reductase enzymes. Further biosynthetic transformations convert sirohydrochlorin to cofactor F430 for an enzyme which catalyzes the release of methane in the final step of methanogenesis.[1][2]

Biosynthesis

Dihydrosirohydrochlorin is derived from a tetrapyrrolic structural framework created by the enzymes deaminase and cosynthetase which transform aminolevulinic acid via porphobilinogen and hydroxymethylbilane to uroporphyrinogen III. The latter is the first macrocyclic intermediate common to haem, chlorophyll, sirohaem and vitamin B12. Uroporphyrinogen III is subsequently transformed by the addition of two methyl groups to form dihydrosirohydrochlorin.[1]

See also

References

  1. ^ a b Battersby, Alan R. (2000). "Tetrapyrroles: The pigments of life: A Millennium review". Natural Product Reports. 17 (6): 507–526. doi:10.1039/B002635M. PMID 11152419.
  2. ^ Mucha, Helmut; Keller, Eberhard; Weber, Hans; Lingens, Franz; Trösch, Walter (1985-10-07). "Sirohydrochlorin, a precursor of factor F430 biosynthesis in Methanobacterium thermoautotrophicum". FEBS Letters. 190 (1): 169–171. doi:10.1016/0014-5793(85)80451-8.