Advantages and Application of 5′ -MMTr in Purine Bases for Oligo Synthesis:
- Use of more potent activator such as 5-(Benzylmercapto)-1H-tetrazole (BTT, pKa=4.08),1 5-Ethylthiotetrazole (ETT, pKa= 4.28),1 which are more acidic in nature compared to 1-H-Tetrazole (pKa= 4.89)1, might lead to the removal of the DMTr group from purine bases during the coupling step of oligo synthesis, thereby causing undesired M+1 oligo growth.
- Since purine bases, A & G, cleave at the 5′-DMTr at a much higher rate than 5′-MMTr, the 5′-MMTr protected nucleoside phosphoramidites is preferred; thus offering a minimal level of M+1 impurities.
References:
1) Welz, R.; Muller, S. Tet. Lett. 2002, 43, 795-797.