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Synthesis and Characterization of Oligonucleotides Containing 2′-Deoxyxanthosine Using Phosphoramidite Chemistry

✍ Scribed by Simona C. Jurczyk; Jennifer Horlacher; Kevin G. Devined; Steven A. Benner; Thomas R. Battersby

Publisher
John Wiley and Sons
Year
2000
Tongue
German
Weight
176 KB
Volume
83
Category
Article
ISSN
0018-019X

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✦ Synopsis

Dedicated to Prof. Colin B. Reese on the occasion of his 70th birthday

Oligodeoxynucleotides containing 2'-deoxyxanthosine (X d ) were synthesized in good yield from a O 2 ,O 6bis2-(4-nitrophenyl)ethyl-protected phosphoramidite of X d . Attempts to synthesize a O 6 -monoNPEprotected 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.

Scheme 1 a) AcOH, NaNO 2 ; 57%. b) NH 3 , H 2 O/MeOH; 99%. c) (MeO) 2 TrCl, pyridine; 37%. d) 2-Cyanoethyl diisopropylphosphoramidochloridite, i Pr 2 NEt, CH 2 Cl 2 ; 42% 4, 7% 6.

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