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2‐Azapurine Nucleosides: Synthesis, Properties, and Base Pairing of Oligonucleotides
Author(s) -
Budow Simone,
Seela Frank
Publication year - 2010
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201000162
Subject(s) - chemistry , phosphoramidite , oligonucleotide , nucleobase , ring (chemistry) , stereochemistry , combinatorial chemistry , base pair , nucleic acid , nucleotide , dna , yield (engineering) , glycosylation , uracil , oligonucleotide synthesis , crystallography , organic chemistry , biochemistry , materials science , metallurgy , gene
This review deals with 2‐azapurine (imidazo[4,5‐ d ] [1,2,3]triazine) nucleosides and closely related analogs. Different routes are described to yield the desired target compounds, including a sequence of ring‐opening and ring‐closure reactions performed on purine nucleosides or direct glycosylation of a 2‐azapurine nucleobase with a sugar halide. Further, physical and spectroscopic properties of 2‐azapurine nucleosides are discussed, including fluorescence, 13 C‐NMR data, single‐crystal X‐ray analyses, and conformation studies on selected compounds; new biological data are presented. The second part of this review is dedicated to oligonucleotides containing 2‐azapurines, including building‐block (phosphoramidite) preparation and their use in solid‐phase oligonucleotide synthesis. Base‐pairing properties of 2‐azapurine nucleosides as surrogates of canonical constituents of DNA were evaluated.