Roquefortine C

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Roquefortine C
Chemical structure of roquefortine C
Names
Preferred IUPAC name
(3E,5aS,10bR,11aS)-3-[(1H-Imidazol-5-yl)methylidene]-10b-(2-methylbut-3-en-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9+/t17-,20-,22+/m0/s1 ☒N
    Key: SPWSUFUPTSJWNG-JJUKSXGLSA-N ☒N
  • InChI=1/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9+/t17-,20-,22+/m0/s1
    Key: SPWSUFUPTSJWNG-JJUKSXGLBA
  • CC(C)(C=C)[C@@]12C[C@H]3C(=O)N/C(=C/c4cnc[nH]4)/C(=O)N3[C@@H]1Nc5c2cccc5
Properties
C22H23N5O2
Molar mass 389.5 g/mol
Appearance White to off-white solid
Soluble in ethanol, methanol, DMF or DMSO
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Roquefortine C is a

Danish Blue, Stilton and Gorgonzola
.

Roquefortine C is a cyclodipeptide mycotoxin derived from the diketopiperazine cyclo(Trp-dehydro-His) and is a relatively common fungal metabolite produced by a number of Penicillium species. It is also considered one of the most important fungal contaminants of carbonated beverages, beer, wine, meats, cheese and bread.

haemoproteins.[4][9]

Roquefortine C contains the unusual E-dehydrohistidine moiety, a system that typically undergoes facile

Z-isomer of roquefortine C.[10]

Isomerisation of Roquefortine C to Isoroquefortine C
Isomerisation of Roquefortine C to Isoroquefortine C

However isoroquefortine C is not a natural product and in contrast to roquefortine C does not bind iron. Both have been synthesised.[10]

Related compounds

References

  1. PMID 22575049
    .
  2. PMID 15734568
    .
  3. S2CID 1334464
    .
  4. ^
    PMID 11559041
    .
  5. ^ SCBT. "Roquefortine - A potent neurotoxin produced most notably by Penicillium species". {{cite journal}}: Cite journal requires |journal= (help)
  6. ^ EPA. "Penicillium roqueforti Final Risk Assessment". {{cite journal}}: Cite journal requires |journal= (help)
  7. PMID 11271775
    .
  8. PMID 2231314
    .
  9. S2CID 9880652
    .
  10. ^
    PMID 18412344
    .

External links
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