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Literature DB >> 24794109

Stability studies on the newly discovered cyclic form of tRNA N(6)-threonylcarbamoyladenosine (ct(6)A).

Michal Matuszewski¹, Elzbieta Sochacka².

Abstract

A cyclic form of N(6)-threonylcarbamoyladenosine bearing an oxazolone moiety (ct(6)A) was discovered very recently at the position 37 in several tRNA sequences. Our study on the synthesized 5',3',2'-O-acetylated derivative of ct(6)A confirmed high stability of the modified nucleoside under physiological conditions (PBS buffer, pH 7.4) and revealed remarkable stability of the oxazolone ring in acidic (100mM HCl, pH 1) and basic (0.1mM NaOH, pH 10) conditions. This feature may allow for the post-synthetic conversion of t(6)A into ct(6)A in assembled oligoribonucleotides.

Entities: Chemical Gene

Keywords: Cyclic N(6)-threonylcarbamoyladenosine (ct(6)A); Modified nucleosides; N(6)-threonylcarbamoyladenosine (t(6)A); Oxazolones; tRNA

Mesh：

Substances：

Year: 2014 PMID： 24794109 DOI： 10.1016/j.bmcl.2014.04.048

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

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Cited

6 in total

Review 1. The Importance of Being Modified: The Role of RNA Modifications in Translational Fidelity.

Authors: Paul F Agris; Amithi Narendran; Kathryn Sarachan; Ville Y P Väre; Emily Eruysal
Journal: Enzymes Date: 2017-04-22

2. Identification of 2-methylthio cyclic N6-threonylcarbamoyladenosine (ms2ct6A) as a novel RNA modification at position 37 of tRNAs.

Authors: Byeong-Il Kang; Kenjyo Miyauchi; Michal Matuszewski; Gabriel Silveira D'Almeida; Mary Anne T Rubio; Juan D Alfonzo; Kazuki Inoue; Yuriko Sakaguchi; Takeo Suzuki; Elzbieta Sochacka; Tsutomu Suzuki
Journal: Nucleic Acids Res Date: 2017-02-28 Impact factor: 16.971

Stability studies on the newly discovered cyclic form of tRNA N(6)-threonylcarbamoyladenosine (ct(6)A).

Review 1. The Importance of Being Modified: The Role of RNA Modifications in Translational Fidelity.

2. Identification of 2-methylthio cyclic N6-threonylcarbamoyladenosine (ms2ct6A) as a novel RNA modification at position 37 of tRNAs.

Review 3. Chemical and Conformational Diversity of Modified Nucleosides Affects tRNA Structure and Function.

4. A hydantoin isoform of cyclic N6-threonylcarbamoyladenosine (ct6A) is present in tRNAs.

Review 5. Celebrating wobble decoding: Half a century and still much is new.

Review 6. Nucleoside modifications in the regulation of gene expression: focus on tRNA.