Hydrolysis of Esters of Monoribonucleotides

Brown, D. M.; Magrath, D. I.; Neilson, Alasdair H.; Todd, A. R.

doi:10.1038/1771124a0

Cited by 78 publications

(39 citation statements)

References 8 publications

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“…It is known that 2'-OH nucleophilic assistance causes RNA to undergo rapid hydrolysis in neutral aqueous media and under physiological conditions. [9,10] Here we point out the distinction between this mechanism, which involves nucleophilic participation of the vicinal hydroxyl group, and our proposed mechanism, in which the hydroxyl group activates an ester by intramolecular general acid catalysis. In polar solvents which can act as hydrogen-bond donors, such as water, the hydrogen-bond acceptor (the phosphate residue) and the intramolecular donor (the adjacent OH group) are solvated separately.…”

Section: Medium-controlled Intramolecular Catalysis In the Direct Synmentioning

confidence: 96%

Medium-Controlled Intramolecular Catalysis in the Direct Synthesis of 5′-O-Protected Ribonucleoside 2′- and 3′-Dialkylphosphates

Roussev

Ivanova

Bratovanova

et al. 2000

Angew. Chem. Int. Ed.

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Section: Medium-controlled Intramolecular Catalysis In the Direct Synmentioning

confidence: 96%

Medium-Controlled Intramolecular Catalysis in the Direct Synthesis of 5′-O-Protected Ribonucleoside 2′- and 3′-Dialkylphosphates

Roussev

Ivanova

Bratovanova

et al. 2000

Angew. Chem. Int. Ed.

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“…Understanding the detailed mechanisms of catalysis used by enzymes that cleave RNA via internal phosphoester transfer has been a major research focus since RNA strand scission was described in the early 1950s (Bacher and Kauzmann 1952;Todd 1952, 1953;Lipkin et al 1954;Brown et al 1956). This reaction proceeds when the 2Ј-oxygen atom adjacent to a given internucleotide linkage executes a nucleophilic attack on the phosphorus center (Fig.…”

Section: Introductionmentioning

confidence: 99%

Ribozyme speed limits

Emilsson¹,

Nakamura²,

Roth³

et al. 2003

RNA

203

273

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The speed at which RNA molecules decompose is a critical determinant of many biological processes, including those directly involved in the storage and expression of genetic information. One mechanism for RNA cleavage involves internal phosphoester transfer, wherein the 2-oxygen atom carries out an S N 2-like nucleophilic attack on the adjacent phosphorus center (transesterification). In this article, we discuss fundamental principles of RNA transesterification and define a conceptual framework that can be used to assess the catalytic power of enzymes that cleave RNA. We deduce that certain ribozymes and deoxyribozymes, like their protein enzyme counterparts, can bring about enormous rate enhancements.

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“…Studies on the chemical stability of RNA, particularly on alkaline hydrolysis, started in the early 1950s (Brown, Magrath, Neilson, & Todd, 1956;Lipkin, Talbert, & Cohn, 1954). The chemical structure of RNA is shown in Figure 15(A) below.…”

Section: Stability Of Mrnamentioning

confidence: 99%

“…The cyclic phosphate rapidly hydrolyzes to a mixture of 2'-and 3'-phosphates (Brown et al, 1956;Mikkola, Kosonen, & Lonnberg, 2002;Oivanen, Kuusela, & Lonnberg, 1998). The presence of this hydroxyl group at the 2'-position on the ribose makes RNA a more unstable molecule and prone to strand cleavage.…”

Section: Stability Of Mrnamentioning

confidence: 99%