Chemical synthesis of an RNA sequence containing 2-thiocytidine (s2C): the DY647 labelled anticodon stem and loop sequence of Staphylococcus aureus tRNAArg (s2C32, mnm5U34, t6A37)

被引：10

作者：

Leszczynska, Grazyna ^{[1
]}

Pieta, Jakub ^{[1
]}

Sproat, Brian ^{[2
]}

Malkiewicz, Andrzej ^{[1
]}

机构：

[1] Tech Univ Lodz, Inst Organ Chem, PL-90924 Lodz, Poland

[2] Chemconsilium GCV, B-2221 Booischot, Belgium

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 34期

关键词：

tRNA modified compounds; RNA fluorescent tag; Solid supported synthesis; 2-Thiocytidine (s(2)C); MODIFIED NUCLEOSIDES; PHOSPHORAMIDITE CHEMISTRY; OLIGONUCLEOTIDE SYNTHESIS; MODIFIED NUCLEOTIDES; TRNA(LYS); DESULFURIZATION; 2-THIOURIDINE; DERIVATIVES;

D O I：

10.1016/j.tetlet.2011.06.078

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Incorporation of 2-thiocytidine (s(2)C) into a DY647 labelled 17-mer RNA sequence corresponding to the anticodon stem loop of Staphylococcus aureus tRNA(Arg) has been achieved by phosphoramidite chemistry. Key to the success was the use of dilute iodine for the P(III) to P(V) oxidation step plus the choice of the trimethylsilylethyl (tse) ester as protection for the threonyl carboxyl group of t(6)A. In trial experiments with N-4-benzoyl-2-thiocytidine, the use of dilute t-BuOOH in toluene as an alternative oxidising agent caused substantial desulfurization. (C)2011 Elsevier Ltd. All rights reserved.

引用

页码：4443 / 4447

页数：5