Polymer support synthesis : XII. Derivatization with the 4-decyloxytrityl group as an aid in the affinity chromatography of oligo- and polynucleotides

Abstract

In a continuation of previous studies on trityl groups substituted with long alkyl chains as affinity-protecting groups for oligonucleotides, the use of the (4-decyloxyphenyl)diphenylmethyl (DTr) group as an aid in the separation of solid-phase products has been investigated. This substituent, which can be introduced and removed from the 5′-position in a similar manner to the di- p-anisylphenylmethyl group, helps in the purification of deoxypolynucleotides with up to 140 bases. Their retention time was shown to depend not only on the length of the nucleotide chain and alkyl substituent, but also on the elution gradient rate. In oligoribonucleotide synthesis, the DTr group allows the purification of partially protected sequences, which are more stable to enzymatic degradation and, therefore, more suitable for handling and storage.