Design and Synthesis of Triazole-Linked xylo-Nucleoside Dimers

Smriti Srivastava; Sunil K Singh; Vivek K Sharma; Priyanka Mangla; Carl E Olsen; Ashok K Prasad

doi:10.1080/15257770.2015.1004341

Design and Synthesis of Triazole-Linked xylo-Nucleoside Dimers

Nucleosides Nucleotides Nucleic Acids. 2015;34(6):388-99. doi: 10.1080/15257770.2015.1004341.

Authors

Smriti Srivastava¹, Sunil K Singh, Vivek K Sharma, Priyanka Mangla, Carl E Olsen, Ashok K Prasad

Affiliation

¹ a Bioorganic Laboratory, Department of Chemistry , University of Delhi , Delhi , India.

PMID: 25965328
DOI: 10.1080/15257770.2015.1004341

Abstract

Three triazole-linked nonionic xylo-nucleoside dimers T(L)-t-T(xL), T(L)-t-A(BzxL) and T(L)-t-C(BzxL) have been synthesized for the first time by Cu(I) catalyzed azide-alkyne [3 + 2] cycloaddition reaction (CuAAC) of 1-(3'-azido-3'-deoxy-2'-O,4'-C-methylene-β-D-ribo-furanosyl)thymine with different alkynes, i.e., 1-(5'-deoxy-5'-C-ethynyl-2'-O,4'-C-methylene-β-D-xylofuranosyl)thymine, 9-(5'-deoxy-5'-C-ethynyl-2'-O,4'-C-methylene-β-D-xylo-furanosyl)-N6-benzoyladenine and 1-(5'-deoxy-5'-C-ethynyl-2'-O,4'-C-methylene-β-D-xylofuranosyl)-N4-benzoylcytosine in 90%-92% yields. Among the two Cu(I) reagents, CuSO4.5H2O-sodium ascorbate in THF:(t)BuOH:H2O (1:1:1) and CuBr.SMe2 in THF used for cycloaddition (click) reaction, the former one was found to be better yielding than the latter one.

Keywords: Click chemistry; Huisgen-Sharpless-Meldal [3+2] cycloaddition; locked nucleic acid; phosphate backbone modification.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Pyrimidine Nucleosides / chemical synthesis*
Pyrimidine Nucleosides / chemistry
Triazoles / chemistry*
Xylose / chemistry*

Substances

Pyrimidine Nucleosides
Triazoles
Xylose