7-Deazapurine (Pyrrolo[2,3-d]pyrimidine) 2 `-Deoxyribonucleosides: Syntheses and Transformations

Autor(en): Seela, Frank
Budow, Simone
Peng, Xiaohua
Stichwörter: 7-Deazapurine; ACID RELATED-COMPOUNDS; BASE-PAIR STABILITY; CAPILLARY GEL-ELECTROPHORESIS; Chemistry; Chemistry, Organic; CLEAVABLE FLUORESCENT NUCLEOTIDE; CLICK CHEMISTRY; click reaction; cross-coupling; enantiomers; FURANOSIDE PYRANOSIDE ISOMERIZATION; glycosylation; halogenation; NUCLEOSIDE TRIPHOSPHATES; nucleosides; PHASE-TRANSFER GLYCOSYLATION; pyrrolo[2,3-d] pyrimidines; SELECTIVE FLUOROMETRIC DETECTION; sequencing; TERMINAL TRIPLE BONDS; triphosphates
Erscheinungsdatum: 2012
Herausgeber: BENTHAM SCIENCE PUBL LTD
Journal: CURRENT ORGANIC CHEMISTRY
Volumen: 16
Ausgabe: 2
Startseite: 161
Seitenende: 223
Zusammenfassung: 
This review reports on the synthesis of 7-deazapurine (pyrrolo[2,3-d] pyrimidine) 2'-deoxyribonucleosides, including -D-and -L-enantiomers, fluoro derivatives, and 2', 3'-dideoxyribonucleosides. It covers the various aspects of convergent nucleoside synthesis. Stereochemically defined alpha-D and alpha-L2'-deoxyribonucleosides as well as sugar derivatives were prepared by nucleobase anion glycosylation. This glycosylation reaction is regioselective for the pyrrole nitrogen and stereoselective for -nucleoside formation. Common glycosylation protocols lead to 7-deazapurine 2'-deoxyribonucleosides with unusual glycosylation sites. 7-Deazapurine 2', 3'dideoxyribonucleosides were also obtained from 2'-deoxy-or 3'-deoxyribonucleosides by Barton-McCombie deoxygenation, by elimination of sugar hydroxyl groups or by anion glycosylation. Another aspect of the review is the functionalization of pyrrolo[ 2,3-d] pyrimidine nucleosides. A broad range of reporter groups were introduced by the Sonogashira cross coupling or the copper(I)-catalyzed HuisgenMeldal- Sharpless `` click'' reaction. The application of 7-deazapurine nucleosides as antiviral or anticancer agents, and the use of 7deazapurine nucleoside triphosphates in the Sanger dideoxy DNA-sequencing are also reported.
ISSN: 13852728
DOI: 10.2174/138527212798993086

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