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

Authors
JAWORSKAMASLANKA MM KACPERCZYK W KORCZYNSKI D LESNIKOWSKI ZJ
Citation
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
Journal title
ANTISENSE & NUCLEIC ACID DRUG DEVELOPMENT → ACNP
ISSN journal
10872906
Volume
7
Issue
1
Year of publication
1997
Pages
23 - 30
Database
ISI
SICI code
1087-2906(1997)7:1<23:SOSFOP>2.0.ZU;2-H
Abstract
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.