The biosynthesis of 9-[5′-deoxy-5′-(methylthio)-beta-D-xylofuranosyl]adenine (xylosyl-MTA), a naturally occurring analogue of 5′-deoxy-5′-methylthioadenosine (MTA) recently characterized, was studied in the nudibranch mollusc Doris verrucosa. Experiments performed in vivo with putative labelled precursors such as [8-14C]adenine, [Me-14C]methionine and [Me-14C]MTA indicate that xylosyl-MTA originates from MTA. Experiments with MTA double-labelled at critical positions are consistent with a 3′-isomerization of the nucleoside through the formation of a 3′-oxo intermediate. In addition, experiments with the newly synthesized [3′-3H]xylosyl-MTA are indicative for a very low turnover rate of this molecule, which therefore accumulates in the mollusc.
Biosynthesis and metabolism of 9-[5′-deoxy-5′-(methylthio)-β-d-xylofuranosyl]adenine, a novel natural analogue of methylthioadenosine
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M Porcelli, G Cacciapuoti, G Cimino, M Gavagnin, G Sodano, V Zappia; Biosynthesis and metabolism of 9-[5′-deoxy-5′-(methylthio)-β-d-xylofuranosyl]adenine, a novel natural analogue of methylthioadenosine. Biochem J 1 November 1989; 263 (3): 635–640. doi: https://doi.org/10.1042/bj2630635
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