E. Kuylyeheskiely et al., AN EXPEDITIOUS ROUTE TO METHYLPHOSPHONATE ANALOGS OF DNA, Recueil des travaux chimiques des Pays-Bas, 113(1), 1994, pp. 40-44
Protection of the exocyclic amino groups of both nucleobases adenine a
nd guanine with the N,N-dimethylformamidine and cytosine with the isob
utyryl group presents a convenient and economical N-protective-group-s
trategy for the solid-phase synthesis of DNA fragments containing meth
ylphosphonate linkages at predetermined locations. Thus, the post-synt
hesis removal of the N-protective groups with hydrazine hydrate (16 h
at 20-degrees-C) afforded immobilized fragments, which were then cleav
ed from the solid support and deprotected at the phosphorus by treatme
nt with ammonia in methanol (2 h at 20-degrees-C) to yield high-qualit
y products.