Nucleosides, nucleotides and nucleic acids p. 473 - 497 (2007)
Update date:2022-08-04
Topics: Synthesis Experimental Generation Oligonucleotide phosphoramidites trinucleotide randomized
Yagodkin, Andrey
Azhayev, Alex
Roivainen, Jarkko
Antopolsky, Maxim
Kayushin, Alexei
Korosteleva, Maria
Miroshnikov, Anatoly
Randolph, John
Mackie, Hugh
A new method to produce a set of 20 high quality trinucleotide phosphoramidites on a 5-10 g scale each was developed. The procedure starts with condensation reactions of P-components with N-acyl nucleosides, bearing the 3′-hydroxyl function protected with 2-azidomethylbenzoyl, to give fully protected dinucleoside phosphates 13. Upon cleavage of dimethoxytrityl group from 13, dinucleoside phosphates 16 are initially transformed into trinucleoside diphosphates 19 and then the 2-azidomethylbenzoyl is selectively removed under neutral conditions to generate trinucleoside diphosphates 5 in excellent yield. Subsequent 3′-phosphitylation affords target trinucleotide phosphoramidites 7. When mutagenic oligonucleotides are synthesized employing mixtures of building blocks 7 as well as following the new synthetic protocol, representative oligonucleotide libraries are generated in good yields. Copyright Taylor & Francis Group, LLC.
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