Sirohydrochlorin

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Sirohydrochlorin
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C42H46N4O16/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/h13-16,23-24,43-44H,3-12,17-18H2,1-2H3,(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)(H,61,62)/t23-,24-,41+,42+/m1/s1
    Key: AVBHZKNQGDKVEA-ZTKUHGNGSA-N
  • C[C@@]1([C@@H](C2=NC1=CC3=NC(=CC4=C(C(=C(N4)C=C5C(=C(C(=C2)N5)CC(=O)O)CCC(=O)O)CCC(=O)O)CC(=O)O)[C@@]([C@@H]3CCC(=O)O)(C)CC(=O)O)CCC(=O)O)CC(=O)O
Properties
C42H46N4O16
Appearance yellow solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Sirohydrochlorin is a

sirohaem, the iron-containing prosthetic group in sulfite reductase enzymes. It is also the biosynthetic precursor to cofactor F430, an enzyme which catalyzes the release of methane in the final step of methanogenesis.[1]

Structure

Sirohydrochlorin was first isolated in the early 1970s when it was shown to be the metal-free form of the

ferredoxin-nitrite reductase from spinach.[2] Its chemical identity was established by spectroscopy and by total synthesis.[3][4][5]

Biosynthesis

Sirohydrochlorin is derived from a tetrapyrrolic structural framework created by the enzymes

vitamin B12. Uroporphyrinogen III is subsequently transformed by the addition of two methyl groups to form dihydrosirohydrochlorin and this is oxidised by precorrin-2 dehydrogenase to give sirohydrochlorin.[6]

See also

References

  1. doi:10.1016/0014-5793(85)80451-8
    .
  2. PMID 4595566
    .
  3. doi:10.1021/ja00493a031
    .
  4. doi:10.1039/C39780000150
    .
  5. doi:10.1039/C39850001061
    .
  6. PMID 11152419
    .
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