Molybdopterin

Molybdopterin
Names
IUPAC name
[2-amino-4-oxo-6,7-bis(sulfanyl)-3,5,5~{a},8,9~{a},10-hexahydropyrano[3,2-g]pteridin-8-yl]methyl dihydrogen phosphate[1]
Identifiers
3D model (JSmol)
MeSH molybdopterin
UNII
  • [2]: InChI=1S/C10H14N5O6PS2/c11-10-14-7-4(8(16)15-10)12-3-6(24)5(23)2(21-9(3)13-7)1-20-22(17,18)19/h2-3,9,12,23-24H,1H2,(H2,17,18,19)(H4,11,13,14,15,16)
    Key: HPEUEJRPDGMIMY-UHFFFAOYSA-N[3][4]
  • based on the images on this page: NC(=N1)NC(=O)C2=C1N[C@H]3[C@@H](N2)C(S)=C(S)[C@H](O3)COP([O-])([O-])=O
  • from the PubChem page; several discrepancies with images on this page: C(C1C(=C(C2C(O1)NC3=C(N2)C(=O)NC(=N3)N)S)S)OP(=O)(O)O
  • with molybdenum; based on this image: NC(=N1)NC(=O)C2=C1N[C@H]3[C@@H](N2)C(S4)=C(S[Mo]4(=O)(=O)O)[C@H](O3)COP([O-])([O-])=O
Properties
C
10H
10N
5O
6PS
2 + R groups
Molar mass 394.33 g/mol (R=H)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Four steps of molybdenum cofactor (Moco) biosynthetic pathway occurring in bacteria and humans: (i) radical-mediated cyclization guanosine 5'-triphosphate (GTP) to (8S)‑3,8‐cyclo‑7,8‑dihydroguanosine-5́‑triphosphate (3,8‑cH2GTP), (ii) formation of cyclic pyranopterin monophosphate (cPMP) from the 3,8‑cH2GTP, (iii) conversion of cPMP into molybdopterin (MPT), (iv) insertion of molybdate into MPT to form Moco (human enzymes in parentheses).

Molybdopterins are a class of cofactors found in most molybdenum-containing and all tungsten-containing enzymes. Synonyms for molybdopterin are: MPT and pyranopterin-dithiolate. The nomenclature for this biomolecule can be confusing: Molybdopterin itself contains no molybdenum; rather, this is the name of the ligand (a pterin) that will bind the active metal. After molybdopterin is eventually complexed with molybdenum, the complete ligand is usually called molybdenum cofactor.

Molybdopterin consists of a pyranopterin, a complex heterocycle featuring a pyran fused to a pterin ring. In addition, the pyran ring features two thiolates, which serve as ligands in molybdo- and tungstoenzymes. In some cases, the alkyl phosphate group is replaced by an alkyl diphosphate nucleotide. Enzymes that contain the molybdopterin cofactor include xanthine oxidase, DMSO reductase, sulfite oxidase, and nitrate reductase.

The only molybdenum-containing enzymes that do not feature molybdopterins are the nitrogenases (enzymes that fix nitrogen). These contain an iron-sulfur center of a very different type, which also contains molybdenum.[5]

  1. ^ "HPEUEJRPDGMIMY-UHFFFAOYSA-N". pubchem.ncbi.nlm.nih.gov. Retrieved 4 February 2019. IUPAC Name [2-amino-4-oxo-6,7-bis(sulfanyl)-3,5,5~{a},8,9~{a},10-hexahydropyrano[3,2-g]pteridin-8-yl]methyl dihydrogen phosphate
  2. ^ "HPEUEJRPDGMIMY-UHFFFAOYSA-N". pubchem.ncbi.nlm.nih.gov. Retrieved 4 February 2019. InChI InChI=1S/C10H14N5O6PS2/c11-10-14-7-4(8(16)15-10)12-3-6(24)5(23)2(21-9(3)13-7)1-20-22(17,18)19/h2-3,9,12,23-24H,1H2,(H2,17,18,19)(H4,11,13,14,15,16)
  3. ^ "[2-Amino-4-oxo-6,7-bis(sulfanyl)-3,5,5a,8,9a,10-hexahydropyrano[3,2-g]pteridin-8-yl]methyl dihydrogen phosphate". pubchem.ncbi.nlm.nih.gov. Retrieved 4 February 2019. InChI=1S/C10H14N5O6PS2/c11-10-14-7-4(8(16)15-10)12-3-6(24)5(23)2(21-9(3)13-7)1-20-22(17,18)19/h2-3,9,12,23-24H,1H2,(H2,17,18,19)(H4,11,13,14,15,16)
  4. ^ "HPEUEJRPDGMIMY-UHFFFAOYSA-N". pubchem.ncbi.nlm.nih.gov. Retrieved 4 February 2019. InChI Key HPEUEJRPDGMIMY-UHFFFAOYSA-N
  5. ^ Structure, synthesis, empirical formula for the di-sulfhydryl. Archived 2016-06-04 at the Wayback Machine Accessed Nov. 16, 2009.