Base‐Modified Oligodeoxyribonucleotides: Using Pyrrolo[2,3‐d]pyrimidines to Replace Purines
Open Access
- 1 March 2005
- journal article
- unit
- Published by Wiley in Current Protocols in Nucleic Acid Chemistry
- Vol. 20 (1) , 4.25.1-4.25.25
- https://doi.org/10.1002/0471142700.nc0425s20
Abstract
Phosphoramidites are first synthesized from suitably protected 7‐deazapurine 2′‐deoxyribonuclosides that have halogen or alkynyl subsituents at the 7 position. Oligonucleotides containing 7‐deazapurines (pyrrolo[2,3‐d]pyrimidines) in place of the canonical nucleobases are then prepared by solid‐phase synthesis. These oligonucleotides are subsequently allowed to hybridize, and the stabilities of the resulting duplexes are determined. Comparison of Tm values indicates that the presence of 7‐halo or 7‐alkynyl substituents increases duplex stability relative to duplexes involving oligonucleotides that contain the corresponding parent purines.Keywords
This publication has 34 references indexed in Scilit:
- 6-AZAPYRIMIDINE AND 7-DEAZAPURINE 2′-DEOXY-2′-FLUOROARABINONUCLEOSIDES: SYNTHESIS, CONFORMATION AND PROPERTIES OF OLIGONUCLEOTIDESNucleosides, Nucleotides and Nucleic Acids, 2005
- Fluorescence quenching of parallel-stranded DNA bound ethidium bromide: the effect of 7-deaza-2′-deoxyisoguanosine and 7-halogenated derivativesBioorganic & Medicinal Chemistry Letters, 2004
- 7-Deazaisoguanine quartets: self-assembled oligonucleotides lacking the Hoogsteen motifChemical Communications, 1997
- Palladium-Catalyzed Cross Coupling of 7-Iodo-2’-deoxytubercidin with Terminal AlkynesSynthesis, 1996
- Duplex Stabilization of DNA: Oligonucleotides containing 7‐substituted 7‐deazaadeninesHelvetica Chimica Acta, 1995
- Synthesis of Certain 5‐Substituted 2′‐Deoxytubercidin DerivativesHelvetica Chimica Acta, 1994
- 7‐Deazaguanosine: Synthesis of an oligorbonucleotide building block and disaggregation of the U‐G‐G‐G‐G‐U G4 structure by the modified baseHelvetica Chimica Acta, 1993
- Bending of oligonucleotides containing an isosteric nucleobase: 7-deaza-2'-deoxyadenosine replacing dA within d(A)6 tractsBiochemistry, 1989
- 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