887620-15-7Relevant articles and documents
Synthesis and biochemical evaluation of phosphonoformate oligodeoxyribonucleotides
Yamada, Christina M.,Dellinger, Douglas J.,Caruthers, Marvin H.
, p. 5251 - 5261 (2006)
Phosphonoformate oligodeoxyribonucleotides were prepared via a solid phase synthesis strategy. The first step in the preparation of appropriate synthons was condensation of bis(N,N-diisopropylamino)-phosphine and diphenylmethylsilylethyl chloroformate in the presence of sodium metal to yield formic acid, [bis(N,N-diisopropylamino)phosphino]-β- (diphenylmethylsilylethyl) ester. The product of this reaction was then condensed with appropriately protected 2′-deoxynucleosides using 4,5-dicyanoimidazole to yield the 3′-O-phosphinoamidite reactive monomers. The exocyclic amines of cytosine, adenine, and guanine were protected with 9-fluorenylmethyloxycarbonyl, and oligodeoxyribonucleotides were synthesized on controlled pore glass using the hydroquinone-O,O′-diacetic acid linker. Synthons were sequentially added to this support using tetrazole as an activator, oxidized to phosphonoformate, and the transient 5′-protecting group was removed with acid. Following total synthesis of an oligomer, protecting groups were removed with TEMED-HF and products purified by HPLC. These analogues were resistant to nucleases, formed duplexes with complementary RNA (A-form), and, as chimeric oligomers containing phosphate at selected sites, stimulated RNase H1 activity.
