Advances in the Synthesis of 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine 2-Deoxyribonucleosides Including D- and L-Enantiomers, Fluoro Derivatives and 2,3-Dideoxyribonucleosides

Seela, Frank; Peng, Xiaohua; Budow, Simone

doi:10.2174/138527207780059286

Cited by 30 publications

(18 citation statements)

References 135 publications

(253 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[1][2][3] These subjects have already been treated in a number of reviews [4][5][6][7][8][9][10][11][12] (if not otherwise stated systematic numbering is used throughout the manuscript). Pyrrolo [2,3-d]pyrimidine nucleosides are naturally occurring and have been isolated as monomers and as constituents of nucleic acids.…”

Section: Introductionmentioning

confidence: 99%

Studies on the Glycosylation of Pyrrolo[2,3-d] Pyrimidines with 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-β-D-Ribofuranose: The Formation of Regioisomers During Toyocamycin and 7-Deazainosine Syntheses

Leonard

Ingale

Ding

et al. 2009

Nucleosides, Nucleotides & Nucleic Acids

Self Cite

View full text Add to dashboard Cite

Glycosylation of silylated 4-amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d]pyrimidine (9) with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (10) under "one-pot" glycosylation conditions (MeCN, TMSOTf) yielded the N-7 isomer 11 together with the N-1 compound 13 (ratio = 2:1). When the same conditions were applied to 4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine (21) the N-3 isomer 22 was the only glycosylation product formed in almost quantitative yield.

show abstract

Section: Introductionmentioning

confidence: 99%

Studies on the Glycosylation of Pyrrolo[2,3-d] Pyrimidines with 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-β-D-Ribofuranose: The Formation of Regioisomers During Toyocamycin and 7-Deazainosine Syntheses

Leonard

Ingale

Ding

et al. 2009

Nucleosides, Nucleotides & Nucleic Acids

Self Cite

View full text Add to dashboard Cite

show abstract

“…Modified nucleosides are used in these protocols as fluorescent dyes to be anchored to them without disturbing the DNA structure (6,7). 7-Deazapurine nucleoside triphosphates are commonly used for these purposes (6–8). Thus, the knowledge about their recognition properties and base discrimination is of mutual interest.…”

Section: Introductionmentioning

confidence: 99%

pH-Dependent mismatch discrimination of oligonucleotide duplexes containing 2′-deoxytubercidin and 2- or 7-substituted derivatives: protonated base pairs formed between 7-deazapurines and cytosine

Peng

Seela

2006

Nucleic Acids Research

Self Cite

View full text Add to dashboard Cite

Oligonucleotides incorporating 2′-deoxytubercidin (1a), its 2-amino derivative 2a and related 2-, or 7-substituted analogs (1d, 2b–d, 3 and 4) are synthesized. For this purpose, a series of novel phosphoramidites are prepared and employed in solid-phase synthesis. Hybridization experiments performed with 12mer duplexes indicate that 7-halogenated nucleosides enhance the duplex stability both in antiparallel and parallel DNA, whereas 2-fluorinated 7-deaza-2′-deoxyadenosine residues destabilize the duplex structure. The 7-deazaadenine nucleosides 1a, 1d and their 2-amino derivatives 2a–d form stable base pairs with dT but also with dC and dG. The mispairing with dC is pH-dependent. Ambiguous base pairing is observed at pH 7 or under acid conditions, whereas base discrimination occurs in alkaline medium (pH 8.0). This results from protonated base pairs formed between 1a or 2a and dC under neutral or acid condition, which are destroyed in alkaline medium. It is underlined by the increased basicity of the pyrrolo[2,3-d]pyrimidine nucleosides over that of the parent purine compounds (pKa values: 1a = 5.30; 2a = 5.71; dA = 3.50).

show abstract

“…7-Substituted purines are positively charged, while 7-substituted 7-deazapurines are neutral being well accepted by DNA polymerases. Moreover, the C-7 position of 7-deazapurine nucleosides is an ideal place to introduce functionalities, as this site lies in the major groove of DNA [68]. The halogen substituents introduced at position C-7 greatly increase the duplex stability.…”

Section: Fluorinated Deazapurine Nucleosidesmentioning

confidence: 99%

Synthesis and applications of fluorinated nucleoside analogues

Wójtowicz‐Rajchel

2012

Journal of Fluorine Chemistry

View full text Add to dashboard Cite

Advances in the Synthesis of 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine 2-Deoxyribonucleosides Including D- and L-Enantiomers, Fluoro Derivatives and 2,3-Dideoxyribonucleosides

Cited by 30 publications

References 135 publications

Studies on the Glycosylation of Pyrrolo[2,3-d] Pyrimidines with 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-β-D-Ribofuranose: The Formation of Regioisomers During Toyocamycin and 7-Deazainosine Syntheses

Studies on the Glycosylation of Pyrrolo[2,3-d] Pyrimidines with 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-β-D-Ribofuranose: The Formation of Regioisomers During Toyocamycin and 7-Deazainosine Syntheses

pH-Dependent mismatch discrimination of oligonucleotide duplexes containing 2′-deoxytubercidin and 2- or 7-substituted derivatives: protonated base pairs formed between 7-deazapurines and cytosine

Synthesis and applications of fluorinated nucleoside analogues

Contact Info

Product

Resources

About