174462-91-0

Upstream product

• 97-72-3 2-Methylpropionic anhydride 
• 172163-62-1 7-iodo-7-deaza-2'-deoxyguanosine 
• 84955-31-7 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine 
• 3056-12-0 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl chloride 
• 104291-20-5 (2R,3S,5R)-5-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate 
• 1529801-45-3 7-[2-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodo-2-(isobutyrylamino)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 1111663-99-0 6-chloro-7-deaza-N⁽²⁾-isobutyryl-3',5',-di-O-p-toluoyl-2'-deoxyguanosine 
• 1111664-00-6 6-chloro-7-deaza-7-iodo-N⁽²⁾-isobutyryl-3',5',-di-O-p-toluoyl-2'-deoxyguanosine 
• 79-30-1 isobutyryl chloride 

Downstream Products

• 174462-92-1 N-(7-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-iodo-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-isobutyramide 
• 172163-62-1 7-iodo-7-deaza-2'-deoxyguanosine 
• 196925-94-7 N-{7-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-4-oxo-5-[5-(2,2,2-trifluoro-acetylamino)-pent-1-ynyl]-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl}-isobutyramide 
• 196925-91-4 N-(7-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-hex-1-ynyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-isobutyramide 
• 375346-75-1 N-{7-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-prop-1-ynyl]-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl}-isobutyramide 
• 245450-59-3 7-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentafuranosyl)-5-(prop-1-ynyl)-3,7-dihydro-2-(isobutyrylamino)-4H-pyrrolo[2,3-d]pyrimidin-4-one 

Relevant academic research and scientific papers

7-Deaza-2′-deoxyguanosine: Selective Nucleobase Halogenation, Positional Impact of Space-Occupying Substituents, and Stability of DNA with Parallel and Antiparallel Strand Orientation

The positional impact of phenyl or phenyltriazolyl residues on the properties of 7-deaza-2′-deoxyguanosine, such as fluorescence, sugar conformation, and stability in DNA and DNA-RNA double helixes was studied. To this end, regioselective iodination protocols were developed for 7-deaza-2′-deoxyguanosine affording the 7- and 8-iodo isomers. The aromatic side chains were introduced by Suzuki-Miyaura cross-coupling or click reaction. Only the 8-phenyl nucleoside shows strong fluorescence in polar aprotic solvents accompanied by solvatochromism. The conformation of the sugar moiety was shifted toward S due to the bulky 8-substituent. Phosphoramidite building blocks and oligonucleotides were synthesized. 8-Substituted 7-deaza-2′-deoxyguanosines destabilize canonical (aps) DNA as well as DNA with parallel strand (ps) orientation. The base pair stability was maintained when the space-occupying substitutes were located at the 7-position. Unexpectedly, the bulky phenyltriazolyl click residue is well-accommodated at the 7-position of ps DNA and even led to a stabilization of the parallel double helix. CD spectra indicate that functionalization leads only to local distortion of the double helix while the overall structure of aps and ps DNA is maintained.

Nucleoside and oligonucleotide pyrene conjugates with 1,2,3-triazolyl or ethynyl linkers: Synthesis, duplex stability, and fluorescence changes generated by the DNA-dye connector

Fluorescent nucleosides and oligonucleotides functionalized with pyrene were synthesized using 'click' chemistry or the Sonogashira cross-coupling reaction. The dye was connected to position-7 of 7-deaza-2′-deoxyguanosine or to the 2′-deoxyribofuranose moiety. Four different DNA-dye connectors with 1,2,3-triazolyl residues or triple bonds were constructed. Phosphoramidites of the pyrene conjugates (9, 14, 25) were prepared and used in solid-phase synthesis. Short linkers (2, 4) destabilize DNA, while long linkers (1) increased duplex stability. Nucleosides and oligonucleotides with single dye incorporations show linker dependent fluorescence. Linker dependent excimer emission with pyrenes in proximal positions was also observed. A 'superchromophore' formed by the 7-deaza-2′-deoxyguanosine ethynylpyrene conjugate shows strong red shifted fluorescence emission at 495 nm.

Phosphoramidites and oligonucleotides containing 7-deazapurines and pyrimidines carrying aminopropargyl side chains

The synthesis of phosphoramidites containing 7-deazaguanine, 7-deazaadenine, uracil and cytosine carrying aminopropargyl chains is described. The corresponding oligonucleotides are stabilized in duplexes thermally as well as against degradation by exonucl

Modified oligonucleotides, their preparation and their use

Modified oligonucleotides which possess at least one substituted 7-deazapurine base form more stable hybridization complexes with nucleic acids than unsubstituted analogs. They are useful as inhibitors of gene expression, as probes for detecting nucleic a

Duplex stability of oligonucleotides containing 7-substituted 7-deaza- and 8-aza-7-deazapurine nucleosides

The synthesis of 7-substituted 7-deaza- and 8-aza-7-deazapurine 2'deoxyribonucleosides, their incorporation into oligonucleotides, and the stability of corresponding duplexes is described.

Duplex Stability of 7-Deazapurine DNA: Oligonucleotides Containing 7-Bromo- or 7-Iodo-7-deazaguanine

The oligonucleotide building blocks, the phosphonates 1a, b and the phosphoramidites 2a, b derived from 7-iodo- and 7-bromo-7-deaza-2'-deoxyguanosines 3a, b were prepared.They were employed in solid-phase oligonucleotide synthesis of the alternating octam