STUDIES ON STEREOSPECIFIC FORMATION OF P-CHIRAL INTERNUCLEOTIDE LINKAGE - SYNTHESIS OF ALL-RP AND ALL-SP METHYLPHOSPHONATE PENTANUCLEOTIDE D(MMTRA(PME)T(PME)T(PME)C(PME)TAC) VIA GRIGNARD ACTIVATED COUPLING
Mm. Jaworskamaslanka et al., STUDIES ON STEREOSPECIFIC FORMATION OF P-CHIRAL INTERNUCLEOTIDE LINKAGE - SYNTHESIS OF ALL-RP AND ALL-SP METHYLPHOSPHONATE PENTANUCLEOTIDE D(MMTRA(PME)T(PME)T(PME)C(PME)TAC) VIA GRIGNARD ACTIVATED COUPLING, ANTISENSE & NUCLEIC ACID DRUG DEVELOPMENT, 7(1), 1997, pp. 23-30
Citations number
33
Categorie Soggetti
Medicine, Research & Experimental","Biothechnology & Applied Migrobiology
Synthesis of stereoregular 3',5'-protected all-Rp and all-Sp methylpho
sphonate heterooligonucleotides d(MMTrA(PMeT?(PMe)T(PMe)C(PMe)TAc) (12
) complementary to the fragment of HIV-1 splicing acceptor site was ac
hieved via stereocontrolled formation of internucleotide linkage. The
coupling was based on the transesterification of P-stereodefined monom
er type of 5'-O-monomethoxytrityl-2'-O-deoxynucleos 3'-O-[O-(4-nitroph
enyl)methylphosphonate]. The nucleophile was a t-butylmagnesium chlori
de activated 5'-terminal hydroxyl function of the growing oligonucleot
ide chain. This and other P-homochiral oligomers will be used as build
ing blocks for the synthesis of biologically significant, longer stere
oregular oligonucleotides.