Synthesis and Application of Isosteric Purine 2′-Deoxyribofuranosides
- 1 January 1987
- journal article
- plenary lectures
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 6 (1-2) , 11-23
- https://doi.org/10.1080/07328318708056176
Abstract
The diastereoselective synthesis of several pyrrolo[2,3-d]- and pyrazolo[3,4-d]pyrimidine 2′-deoxy-ribofuranosides employing l-chloro-2-deoxy-3,5-di-0-(p-tolu-oyl)-a-D-erythropentofuranose and the nucleobase anion, generated by liquid-liquid or solid-liquid phase-transfer catalysis, is described. Appropriately protected phosphoramidites of 8-aza-7-deaza-2′-deoxyadenosine and 2′-deoxytubercidin were prepared and employed in solid-phase synthesis of palindromic DNA-fragments. The replacement of dA residues by deoxytubercidin within the Eco RI recognition site d(GAATTC) of the dodecamer d(GTAGAATTCTAC) gave evidence for purine N-7 binding to the endodeoxyribonuclease. The interpretation of similar experiments carried out on d(CGCGAATTCGCG) was obscured because of hairpin formation.Keywords
This publication has 23 references indexed in Scilit:
- Palindromic oiigonucleotides containing 7-deaza-2' -deoxyguanosine: solid-phasesynthesisof d[(p)GG*AATTCC] octamers and recognition by the endodeoxyribonncleaseEcoRINucleic Acids Research, 1986
- Synthese von 7‐Desaza‐2′‐desoxyinosin durch PhasentransferglycosylierungEuropean Journal of Organic Chemistry, 1985
- 7‐Desaza‐Isostere von 2′‐Desoxyxanthosin und 2′‐Desoxyspongosin — Synthese via Glycosylierung von 2,4‐Dichlor‐7H‐pyrrolo[2,3‐d]pyrimidinEuropean Journal of Organic Chemistry, 1985
- Synthesis of 2-amino-7-(2'-deoxy-.beta.-D-erythro-pentofuranosyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one, a new isostere of 2'-deoxyguanosineThe Journal of Organic Chemistry, 1983
- 2′‐Desoxytubercidin – Synthese eines 2′‐Desoxyadenosin‐Isosteren durch PhasentrasferglycosylierungEuropean Journal of Organic Chemistry, 1983
- Nucleosides, 381) The Ribonucleosides of AllopurinolEuropean Journal of Inorganic Chemistry, 1981
- Modified Bases in Bacteriophage DNAsAnnual Review of Microbiology, 1980
- Synthesis of 5-methyltubercidin and its .ALPHA.-anomer via condensation of the anion of 4-methoxy-5-methyl-2-methylthiopyrrolo [2,3-d] pyrimidine and 2,3,5-tri-O-benzyl-D-ribofuranosyl bromide.Agricultural and Biological Chemistry, 1977
- Oligonucleotidic compounds. XXXIV. Preparation of some β-L-ribonucleosides, their 2'(3')-phosphates and 2',3'-cyclic phosphatesCollection of Czechoslovak Chemical Communications, 1969
- α‐ThymidinEuropean Journal of Inorganic Chemistry, 1960