Backbone modified oligodeoxynucleotides: stereoselective synthesis of methylphosphonates and HIV inhibitory capacity of phosphorothioates. NLM AIDSLINE Important note: Information in this article was accurate in 1993. The state of the art may have changed since the publication date.

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Backbone modified oligodeoxynucleotides: stereoselective synthesis of methylphosphonates and HIV inhibitory capacity of phosphorothioates.

Nucleic Acids Symp Ser. 1991;(24):83-6. Unique Identifier : AIDSLINE MED/93027440
Engels JW; Daum T; Frauendorf A; Luking S; Mag M; Muller WE; Muth J; Rosmanitz P; Institut fur Organische Chemie, Universitat Frankfurt, FRG.

Abstract: Oligonucleotides bearing phosphorothioate linkages of the HIV tatIII splice acceptor site were synthesized by automated solid phase synthesis. Especially 5'- and 3'-end capped thioates of the sequence 5'-ACACCCAATTCTGAAAATGG-3' show microM inhibition of HIV replication. ODN-methylphosphonates of defined stereochemistry were obtained with suitably modified proline phosphonamidite derivatives as monomeric building blocks. Asymmetric induction for nucleosidephosphonamidates up to 5:1 (Rp:Sp rsp. Sp:Rp depending on configuration of proline-moiety) could be reached. The intermediate phosphonamidite can be further reacted to dinucleoside methylphosphonates of enriched diastereomeric excess.
Keywords: Antiviral Agents/*CHEMICAL SYNTHESIS/PHARMACOLOGY Base Sequence HIV/*DRUG EFFECTS Indicators and Reagents Models, Molecular Molecular Sequence Data Nuclear Magnetic Resonance Nucleic Acid Conformation Oligodeoxyribonucleotides/CHEMISTRY/*CHEMICAL SYNTHESIS/ PHARMACOLOGY Phosphonic Acids/CHEMISTRY/*CHEMICAL SYNTHESIS/PHARMACOLOGY Support, Non-U.S. Gov't Thiophosphoric Acid Esters/CHEMISTRY/*CHEMICAL SYNTHESIS/ PHARMACOLOGY JOURNAL ARTICLEKWDantiviralagents/KWDchemicalsynthesis/pharmacologybasesequencehiv/KWDdrugeffectsindicatorsandreagentsmodels,molecularmolecularsequencedatanuclearmagneticresonancenucleicacidconformationoligodeoxyribonucleotides/chemistry/KWDchemicalsynthesis/pharmacologyphosphonicacids/chemistry/KWDchemicalsynthesis/pharmacologysupport,non-uKWDsKWDgov'tthiophosphoricacidesters/chemistry/KWDchemicalsynthesis/pharmacologyjournalarticle
930130
M9311144

Copyright © 1993 - National Library of Medicine. Reproduced under license with the National Library of Medicine, Bethesda, MD.

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