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. 2014 Aug 1;24(15):3243-6.
doi: 10.1016/j.bmcl.2014.06.025. Epub 2014 Jun 18.

Formation of the N(2)-acetyl-2,6-diaminopurine oligonucleotide impurity caused by acetyl capping

Andrew A Rodriguez  1 , Isaiah Cedillo  2 , Brendan P Mowery  2 , Hans J Gaus  2 , Seetha S Krishnamoorthy  2 , Andrew K McPherson  2
Affiliations

Formation of the N(2)-acetyl-2,6-diaminopurine oligonucleotide impurity caused by acetyl capping

Andrew A Rodriguez et al. Bioorg Med Chem Lett. .

Abstract

The acetyl 'capping' reaction routinely employed during phosphorothioate oligonucleotide synthesis has been implicated in the formation of an impurity species with a mass 41 amu greater than the expected oligonucleotide molecule. The impurity has been found to arise by conversion of a protected guanine nucleobase to N(2)-acetyl-2,6-diaminopurine. A two-part mechanism is proposed consisting of transamidation of the protecting group on guanine and substitution of guanine's O(6) atom.

Keywords: Acetyl; Capping; Guanine; Guanosine; Impurity; Modification; Oligonucleotide; Solid-phase; Synthesis.

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