Tetrahydrofoolihappo

Tetrahydrofoolihappo
Tunnisteet
IUPAC-nimi (2S)-2-[[4-[(2-amino-4-okso-5,6,7,8-tetrahydro-1H-pteridin-6-yyli)metyyliamino]bentsoyyli]amino]pentaanidihappo
CAS-numero 135-16-0
PubChem CID 135398650
SMILES C1C(NC2=C(N1)NC(=NC2=O)N)CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O[1]
Ominaisuudet
Molekyylikaava C19H23N7O6
Moolimassa 445,444 g/mol
Liukoisuus veteen Liukenee veteen

Tetrahydrofoolihappo (C19H23N7O6) on foolihapon johdannaisiin kuuluva orgaaninen yhdiste. Yhdiste on tärkeä koentsyymi useissa entsymaattisissa reaktioissa niin aitotumaisissa kuin esitumallisissa soluissakin.

Ominaisuudet, biosynteesi ja biologinen rooli

Tetrahydrofoolihappo on huoneenlämpötilassa kiteistä ainetta. Yhdisteen rakenne koostuu bisyklisestä pteridiinirakenteesta, p-aminobentsoehaposta johdetusta ryhmästä ja glutamiinihappo-osasta. Tetrahydrofoolihappo hapettuu suhteellisen helposti ilman hapen vaikutuksesta dihydrofoolihapoksi (C19H21N7O6). Yhdisteen stabiilius riippuu huomattavasti pH:sta ja stabiilein se pH:n ollessa 7,4. Tetrahydrofoolihappo on optisesti aktiivinen yhdiste ja sen ominaiskiertokyky natriumhydroksidia sisältävässä vesiliuoksessa on –16,9. Tetrahydrofoolihappoa voidaan syntetisoida kemiallisesti pelkistämällä foolihappoa happamissa olosuhteissa vedyttämällä tai natriumsyanoboorihydridin avulla.[2][3][4][5][6]

Nisäkkäät pelkistävät foolihapon ensin dihydrofoolihapoksi ja edelleen dihydrofolaattireduktaasin katalysoimana tetrahydrofoolihapoksi. Nisäkkäät kykeneät biosyntetisoimaan pteridiinirakenteen, mutta eivät liittämään sitä p-aminobentsoehappoon ja glutamiinihappoon. Monet bakteerit sen sijaan kykenevät tekemään tämän. Tetrahydrofoolihappo toimii koentsyyminä useissa aminohappojen ja nukleotidien biosynteesiä katalysoivissa entsyymeissä. Siitä muodostuu myös useita esimerkiksi metyloituja tai formyloituja johdannaisia, jotka ovat niin ikään tärkeässä roolissa aminohappojen ja nukleotidien biosynteeseissä.[2][3][4][5][6]

Lähteet

  1. ↑ Tetrahydrofolic acid – Compound Summary PubChem. NCBI. Viitattu 21.10.2016.
  2. ↑ a b Jeremy M. Berg, John L. Tymoczko & Lubert Stryer: Biochemistry, 7th Edition, s. 689–690, 721. W. H. Freeman and Company, 2012. ISBN 978-0-7167-8724-2 (englanniksi)
  3. ↑ a b Thimma R. Rawalpally: Folic acid, Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons, New York, 2010. Viitattu 23.10.2016
  4. ↑ a b Bernd-Jürgen Weimann, Urs Hengartner, Antoine de Saizieu & Christof Wehrli: Vitamins, 10. Folic Acid, Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, New York, 2007. Viitattu 23.10.2016
  5. ↑ a b Thomas Scott,Eric Ian Mercer: Concise encyclopedia biochemistry and molecular biology, s. 666–667. Walter de Gruyter, 1997. ISBN 978-3110145359 (englanniksi)
  6. ↑ a b Paul M. Dewick: Medicinal Natural Products, s. 126. John Wiley & Sons, 2002. ISBN 9780471496410 Kirja Googlen teoshaussa Viitattu 23.10.2016. (englanniksi)

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