Nucleotide chemistry. 16. Amidine protecting groups for oligonucleotide synthesis

Synthesis and Properties of Oligonucleotides Containing 8-Bromo-2′-Deoxyguanosine

“…6 In this communication we report the synthesis of an 8-bromoguanine phosphoramidite derivative protected with the dimethylformamidine (dmf) 13,14 group and its use in the preparation of oligodeoxynucleotides carrying 8-bromoguanine. Moreover, base-pairing properties of oligodeoxynucleotides containing 8-bromoguanine and their ability to form Z-DNA are described.…”

Formation of N-Branched Oligonucleotides as By-products in Solid-Phase Oligonucleotide Synthesis

“…However, in the case of deoxycytidine, only hindered 4-N-amidino groups have been reported to exhibit sufficient stability for oligonucleotide synthesis (McBride et al, 1986), and their introduction requires the use of amidine acetals, which are not commercially available. Instead of restoring the complete N-protection of supported 2Ј-deoxycytidine, one may envisage the use of universal, nonnucleoside derivatized support, which was reported to prevent the formation of 3Ј-terminal N-branched oligonucleotides (Kurata et al, 2006).…”

Synthesis and Properties of Oligodeoxynucleotides Carrying 2-Aminopurine

“…Synthetic scheme used for the preparation of isobutyryl protected 2-aminopurine phosphoramidite. more labile than the ibu group [32,33]. Recently, the phosphoramidite derivative of 2-aminopurine carrying the dmf group has become commercially available.…”