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Identification of Adducts Formed in the Reaction of the Bacterial Mutagen 3-Chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone with Cytidine

Pluskota-Karwatka D., Munter T., Le Curieux F., Sjöholm R., Koroniak H., Kronberg L.

Polish Journal of Chemistry

2007

Vol. 81, nr 5-6

1145-1157

3-Chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone (CMCF), a strong bacterial mutagen reacts with cytidine in buffered aqueous solutions. The reaction products were separated by preparative HPLC C18 column chromatography and were structurally characterized by UV absorbance, 1H NMR and 13C NMR spectroscopy, and mass spectrometry. The main products were identified as 7-(-D-ribofuranosyl)-4-carboxy-6- oxo-6,7-dihydro-4H-pyrimido[1,6-alfa]pyrimidine-3-carbaldehyde (cM1FA-Cyd), and 7-(beta-D-ribofuranosyl)-6-oxo-6,7-dihydro-4H-pyrimido[1,6-alfa]pyrimidine-3-carbaldehyde (M1FA-Cyd). The highest yields of cM1FA-Cyd andM1FA-Cyd, being 12 and 1mol%respectively, were obtained in the reaction performed at pH 4.6 and 37 graduateC for 7 days. M1FA-Cyd and cM1FA-Cyd are structurally related to pfA-dR, the adduct previously identified in the reaction of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) or 3-chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone (CMCF) with 2'-deoxyadenosine.

Derivatization of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) with butyl alcohols

Nawrocki J., Andrzejewski P., Jeleń H., Wąsowicz M.

Chemia Analityczna

2001

Vol. 46, No. 2

225-237

As a continuation of our earlier research, the paper reports progress in the study on improvement of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) determination in water. In particular, the effect achieved as results of modification of MX with butyl alcohols (n-butanol, isobutanol, sec-butanol and tert-butanol) is reported. Sec-bu-tanol derivatization permits separation of MX enantiomers in the form of diastereo-isomers. Isobutanol derivatization leads to formation of sextet of fragmentation ions of high abundance, which can improve identification of MX in environmental samples.

Prezentowane wyniki są kontynuacją działań w kierunku poprawy analizy 3-chloro-4-(dichlorometyIo)-5-hydroksy-2(5H)-furanonu (MX) w wodzie. Przedstawiono rezultaty zastosowania butanoli (n-butanolu, izobutanolu, sec-butanolu i tert-butanolu) w analizie MX. Derywatyzacja z zastosowaniem jec-butanolu pozwala na rozdzielanie enancjo-merów MX w postaci diastereoizomerów. Zastosowanie izobutanolu prowadzi do powstania sekstetu bardzo intensywnych jonów izotopowych, które mogą ułatwić identyfikację MX w próbkach środowiskowych.