Article ID Journal Published Year Pages File Type
10595559 Bioorganic & Medicinal Chemistry Letters 2013 4 Pages PDF
Abstract
When 8-bromoguanosine was incubated with cysteine at pH 7.4 and 37 °C, a previously unidentified product was formed as a major product in addition to guanosine. The product was identified as a cysteine substitution derivative of guanosine at the 8 position, 8-S-l-cysteinylguanosine. The reaction was accelerated under mildly basic conditions. The cysteine adduct of guanosine was fairly stable and decomposed with a half-life of 193 h at pH 7.4 and 37 °C. Similar results were observed for incubation of 8-bromo-2′-deoxyguanosine with cysteine. The results suggest that 8-bromoguanine in nucleosides, nucleotides, RNA, and DNA can react with thiols resulting in stable adducts.
Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
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