SYNTHESIS AND N-15-NMR AND O-17-NMR SPECTRA OF 5-METHYL(N-15(2))[O-2,O-4-O-17(2)]URIDINE (=(N-15(2))[O-2,O-4-O-17(2)]RIBOSYLTHYMINE)

被引：9

作者：

AMANTEA, A ^{[1
]}

WALSER, M ^{[1
]}

SEQUIN, U ^{[1
]}

STRAZEWSKI, P ^{[1
]}

机构：

[1] UNIV BASEL,INST ORGAN CHEM,CH-4056 BASEL,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1995年 / 78卷 / 05期

关键词：

D O I：

10.1002/hlca.19950780507

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 5-methyl(N-15(2))[O-2,O-4-O-17(2)]uridine (=(N-15(2))[O-2,O-4-O-17(2)]ribosylthymine; 15) was synthesized and analyzed by N-15- and O-17-NMR spectroscopy. (N-15(2))Urea was condensed with 2,3-dibromo-2-methylpropanoyl chloride (3) and cyclized to form ((15)N(2)thymine (5). After glycosidation, the O-17 isotopes were introduced in two separate steps: hydrolytic ring opening of 2,5'-anhydro derivative 9 and hydrolysis of 3-nitro-1H-1,2,4-triazole derivative 12 with labelled water in the presence of a strong base. The N-15- and O-17-NMR spectra (Fig.) of 15 in phosphate-buffered water serve as references for heteronuclear NMR spectra of labelled RNA fragments.

引用

页码：1106 / 1111

页数：6

共 5 条

[1] SYNTHESIS AND CHARACTERIZATION OF OLIGODEOXYNUCLEOTIDES CONTAINING 4-O-METHYLTHYMINE [J].