Molybdopterin

Strukturformel
Allgemeines
Name Molybdopterin
Andere Namen
  • MPT
  • Pyranopterin-dithiolat
Summenformel C10H14N5O6PS2
Externe Identifikatoren/Datenbanken
CAS-Nummer 73508-07-3
PubChem 444331
Wikidata Q619698
Eigenschaften
Molare Masse 395,32 g·mol−1 (R=H)
Sicherheitshinweise
GHS-Gefahrstoffkennzeichnung
keine Einstufung verfügbar[1]
Soweit möglich und gebräuchlich, werden SI-Einheiten verwendet.
Wenn nicht anders vermerkt, gelten die angegebenen Daten bei Standardbedingungen (0 °C, 1000 hPa).

Molybdopterin ist eine chemische Verbindung, die auf einem Pterinring aufbaut. Molybdopterin bildet zusammen mit einem Molybdänion den Molybdän-Cofactor (MoCo).

Eigenschaften

Molybdopterin besteht aus einem Pyranopterin, einem Heterozyklus aus einem Pyranring und einem Pteridinring. Am Pyranring sind zwei Thiolate. In manchen Fällen ist die Alkylphosphatgruppe eine Alkyldiphosphatnukleotidgruppe (aus Adenosindiphosphat).

Verschiedene Enzyme verwenden Molybdopterin.[2] Molybdopterin ist ein Cofaktor der Xanthin-Oxidase, der DMSO-Reduktase, der Sulfitoxidase, der Nitratreduktase, der Ethylbenzendehydrogenase, der Glyceraldehyd-3-phosphat-Ferredoxin-Oxidoreduktase, der Arsenatreduktase (Glutaredoxin) und der Kohlenstoffmonoxid-Dehydrogenase.[2] Weiterhin ist Molybdopterin eine prosthetische Gruppe verschiedener Enzyme wie der Formiat-Dehydrogenase, der Purin-Hydroxylase und der Thiosulfat-Reduktase.[2] Molybdopterin tritt weiterhin in der Aldehydoxidase auf.[3]

In manchen Bakterienarten wird in ihren Oxidoreduktasen am Molybdopterin anstatt Molybdat Wolframat gebunden. Diese Enzyme oxidieren meistens Aldehyde zu Carbonsäuren.[4] Manche Wolframat-bindende Oxidoreduktasen verwenden Selen anstatt des Schwefels.[5][6]

Biosynthese

Molybdopterin-Biosynthese

Molybdopterin wird aus Guanosintriphosphat synthetisiert. Über eine radikalische Reaktion mit S-Adenosylmethionin wird im ersten Zwischenschritt Pyranopterin gebildet. Anschließend erfolgt über drei weitere Reaktionsschritte die Bildung eines Endithiolats. Die Phosphatgruppe wird an Adenosindiphosphat gekoppelt, wodurch das Molybdopterin entsteht.[7]

Die Modelle der aktiven Zentren von Molybdopterin-enthaltenden Enzymen sind von Dithiolen-enthaltenden Liganden abgeleitet.[8]

Einzelnachweise

  1. ↑ Dieser Stoff wurde in Bezug auf seine Gefährlichkeit entweder noch nicht eingestuft oder eine verlässliche und zitierfähige Quelle hierzu wurde noch nicht gefunden.
  2. ↑ a b c Structure, synthesis, empirical formula for the di-sulfhydryl. Accessed Nov. 16, 2009.
  3. ↑ Katharina Munk (Hrsg.): Taschenlehrbuch Biologie. Biochemie – Zellbiologie. (eingeschränkte Vorschau in der Google-Buchsuche). Georg Thieme, Stuttgart 2008, ISBN 978-3-13-144831-6.
  4. ↑ Erik Lassner: Tungsten: Properties, Chemistry, Technology of the Element, Alloys and Chemical Compounds. Springer Science & Business Media, 1999, ISBN 978-0-306-45053-2, S. 409 (eingeschränkte Vorschau in der Google-Buchsuche).
  5. ↑ Stiefel, E. I.: Transition metal sulfur chemistry and its relevance to molybdenum and tungsten enzymes. In: Pure Appl. Chem. 70. Jahrgang, Nr. 4, 1998, S. 889–896, doi:10.1351/pac199870040889 (iupac.org [PDF]).
  6. ↑ Schräder T, Rienhöfer A, Andreesen JR: Selenium-containing xanthine dehydrogenase from Eubacterium barkeri. In: Eur. J. Biochem. 264. Jahrgang, Nr. 3, September 1999, S. 862–71, doi:10.1046/j.1432-1327.1999.00678.x, PMID 10491134 (wiley.com).
  7. ↑ Schwarz, G. and Mendel, R. R.: Molybdenum cofactor biosynthesis and molybdenum enzymes. In: Annu. Rev. Plant Biol. 57. Jahrgang, 2006, S. 623–647, doi:10.1146/annurev.arplant.57.032905.105437, PMID 16669776.
  8. ↑ Kisker, C.; Schindelin, H.; Baas, D.; Rétey, J.; Meckenstock, R.U.; Kroneck, P.M.H.: A structural comparison of molybdenum cofactor-containing enzymes. In: FEMS Microbiol. Rev. 22. Jahrgang, Nr. 5, 1999, S. 503–521, doi:10.1111/j.1574-6976.1998.tb00384.x, PMID 9990727.

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