The products of 5-fluorouridine by the action of the pseudouridine synthase TruB disfavor one mechanism and suggest another.

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Miracco EJ, Mueller EG

The products of 5-fluorouridine by the action of the pseudouridine synthase TruB disfavor one mechanism and suggest another.

J Am Chem Soc. 2011 Aug 10;133(31):11826-9. doi: 10.1021/ja201179f. Epub 2011 Jul 15.

PubMed ID
21744792 [ View in PubMed
]
Abstract

The pseudouridine synthase TruB handles 5-fluorouridine in RNA as a substrate, converting it into two isomeric hydrated products. Unexpectedly, the two products differ not in the hydrated pyrimidine ring but in the pentose ring, which is epimerized to arabinose in the minor product. This inversion of stereochemistry at C2' suggests that pseudouridine generation may proceed by a mechanism involving a glycal intermediate or that the previously proposed mechanism involving an acylal intermediate operates but with an added reaction manifold for 5-fluorouridine versus uridine. The arabino product strongly disfavors a mechanism involving a Michael addition to the pyrimidine ring.

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