The products of 5-fluorouridine by the action of the pseudouridine synthase TruB disfavor one mechanism and suggest another.
The products of 5-fluorouridine by the action of the pseudouridine synthase TruB disfavor one mechanism and suggest another.
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DOI：
10.1021/ja201179f
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发表时间：
2011-08-10
影响因子：
15
通讯作者：
Mueller, Eugene G.
中科院分区：
文献类型：
--
作者：
Miracco, Edward J.;Mueller, Eugene G.
假尿苷合酶TruB处理RNA中的5-氟尿苷作为底物，将其转化为两种异构的水合产物。出乎意料的是，这两种产物的不同之处不在于水合嘧啶环，而在于戊糖环，其在次要产物中已差向异构化为阿拉伯糖。C2′的立体化学反转表明假尿苷的生成可能是通过一种涉及糖基中间体的机制进行的，或者是先前提出的涉及酰基醛中间体的机制，但增加了5-氟尿苷与尿苷的反应歧管。阿糖基产物强烈反对嘧啶环的迈克尔加成机制。
The pseudouridine synthase TruB handles 5-flurouridine in RNA as a substrate, converting it to two isomeric, hydrated products. Unexpectedly, the two products differ not in the hydrated pyrimidine ring but in the pentose ring, which has been 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 with a Michael addition to the pyrimidine ring.
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