TUTCRIS - Tampereen teknillinen yliopisto

TUTCRIS

Ring-chain tautomerism of chlorinated hydroxyfuranones and reaction with nucleosides

Tutkimustuotosvertaisarvioitu

Yksityiskohdat

AlkuperäiskieliEnglanti
Sivut973-980
Sivumäärä8
JulkaisuChemosphere
Vuosikerta38
Numero5
DOI - pysyväislinkit
TilaJulkaistu - helmikuuta 1999
Julkaistu ulkoisestiKyllä
OKM-julkaisutyyppiA1 Alkuperäisartikkeli

Tiivistelmä

Several genotoxic hydroxyfuranones present in chlorine disinfected drinking water, were reacted with adenosine, guanosine, and cytidine in aqueous solution. HPLC analyses with UV detection at 254 and 325 nm showed that adducts were formed. The compounds MCF, 3-chloro-4-methyl-5-hydroxy-2(5H)-furanone and mCMF, 4-(chloromethyl)-5-hydroxy-2(5H)-furanone tautomerized to the corresponding oxobutenoic acids at pH 7.4 and formed 4-(N 6-adenosinyl)-3-formyl-3-butenoic acid (I) as the major product. The hydroxyfuranone MX, 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone reacted with guanosine, and formed 10-formyl-1,N 2-benzoquinone propenoguanosine. The adducts were isolated by C18 column chromatography, and characterized by UV absorbance, 1H spectroscopy, and mass spectrometry.