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Synthesis and Characterization of Oligonucleotides Containing 2′‐Deoxyxanthosine Using Phosphoramidite Chemistry
Author(s) -
Jurczyk Simona C.,
Horlacher Jennifer,
Devined Kevin G.,
Benner Steven A.,
Battersby Thomas R.
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20000705)83:7<1517::aid-hlca1517>3.0.co;2-s
Subject(s) - phosphoramidite , chemistry , oligonucleotide , yield (engineering) , oligonucleotide synthesis , combinatorial chemistry , mass spectrometry , protecting group , aqueous solution , organic chemistry , dna , chromatography , alkyl , biochemistry , materials science , metallurgy
Oligodeoxynucleotides containing 2′‐deoxyxanthosine (X d ) were synthesized in good yield from a O 2 , O 6 ‐bis[2‐(4‐nitrophenyl)ethyl](NPE)‐protected phosphoramidite of X d . Attempts to synthesize a O 6 ‐monoNPE‐protected phosphoramidite resulted in formation of a major by‐product. The NPE protecting groups were removed by treatment with oximate ion after other protecting groups were removed with aqueous NH 4 OH solution. The composition of the synthetic oligonucleotides was verified by enzymatic degradation and MALDI‐TOF mass spectrometry. The efficacy of this procedure allowed isolation of oligodeoxynucleotides containing multiple X d residues.