Synthesis of Purine Cyclonucleoside Having a 8,2'-O-Anhydro Linkage

Ikehara, Morio; Tada, Hiroshi; Muneyama, Kei; Kaneko, Masakatsu

doi:10.1021/ja00965a071

Cited by 21 publications

(10 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2 ‘ ,3 ‘ ,5 ‘ - O -Tridecanoyl-8-oxoguanosine (6). 8-Oxoguanosine was obtained by catalytic hydrogenation (10% Pd/C) of benzyloxy derivative in EtOH−H 2 O (1:1, v/v). 8-Oxoguanosine (218 mg, 0.73 mmol) was dissolved in 12 mL of anhydrous acetonitrile.…”

Section: Methodsmentioning

confidence: 99%

Supramolecular Helices via Self-Assembly of 8-Oxoguanosines

et al. 2003

View full text Add to dashboard Cite

The cooperative effect of solvophobic interactions and hydrogen bonding has been exploited to self-assemble supramolecular helical architectures of 8-oxoguanosines in different environments. This self-assembly into helical structures is completely different from that of the parent guanosines which, in the same experimental conditions, form flat, ribbonlike structures. While optical microscopy and X-ray diffraction suggest a chiral columnar aggregate in the LC phase, NMR and Circular Dichroism reveal the presence of a helical structures in solution. Scanning Tunneling Microscopy made it possible to visualize hexagonally arranged G-quartets on graphite, which are sections of the helices packed with their long axis perpendicular to the basal plane of the substrate. Due to their rectifying electrical properties, such helices are interesting for fabricating (opto)electronic biodevices.

show abstract

Section: Methodsmentioning

confidence: 99%

Supramolecular Helices via Self-Assembly of 8-Oxoguanosines

et al. 2003

View full text Add to dashboard Cite

show abstract

“…Since there seems to be an excellent correlation between the sign of the d line rotation with that of the 260-µ Cotton effect for both purine and pyrimidine nucleosides it may be presumed that these materials will also exhibit negative Cotton effects. The compounds which fall into this class are: (1) 3,5'-cyclo-6-dimethylamino-9-(3'-deoxy-/3-D-ribofuranosyl)purine 2',3'-carbonate(Baker and Joseph, 1955); (2) 8,2'-cyclo-2-chloro-8-mercapto-9-0-D-arabinofuranosyladenine(Ikehara and Tada, 1965); (3) 8,2'-cyclo-8-hydroxy-9-/3-D-arabinofuranosyladenine(Ikehara et al, 1966). Although two of these compounds are arabinose derivatives, it has been shown that the sign of the Cotton band is the same in arabinosides as in the corresponding ribosides(Price?…”

mentioning

confidence: 99%

The Conformation of Ribonucleosides in Solution. The Effect of Structure on the Orientation of the Base^*

Wa¹,

Sh²

1967

Biochemistry

View full text Add to dashboard Cite

“…205 °C decomp. (Lit 61. 210 °C) IR (Solid, cm −1 ) 3,297 (NH 2 ), 3,142 (OH), 2,962, 2,883 (CH), 1,667 (C=C), 1,623 (C=N).…”

Section: Methodsmentioning

confidence: 99%

“…(Lit. 61 210 °C) IR (Solid, cm −1 ) 3,297 (NH 2 ), 3,142 (OH), 2,962, 2,883 (CH), 1,667 (C=C), 1,623 (C=N). 1 H NMR (600 MHz, D 2 O) 8.16 (1H, s, H2), 6.71 (1H, d, J =5.5 Hz, H1′), 5.90 (1H, d, J =5.5 Hz, H2′), 4.72 (1H, s, H3′), 4.40 (1H, ddd, J =5.5, 5.4, 4.3 Hz, H4′), 3.55 (1H, ABX, J =12.7, 4.3 Hz, H5′), 3.48 (1H, ABX, J =12.7, 5.4 Hz, H5′).…”

Section: Methodsmentioning

confidence: 99%

Divergent prebiotic synthesis of pyrimidine and 8-oxo-purine ribonucleotides

et al. 2017

View full text Add to dashboard Cite

Understanding prebiotic nucleotide synthesis is a long standing challenge thought to be essential to elucidating the origins of life on Earth. Recently, remarkable progress has been made, but to date all proposed syntheses account separately for the pyrimidine and purine ribonucleotides; no divergent synthesis from common precursors has been proposed. Moreover, the prebiotic syntheses of pyrimidine and purine nucleotides that have been demonstrated operate under mutually incompatible conditions. Here, we tackle this mutual incompatibility by recognizing that the 8-oxo-purines share an underlying generational parity with the pyrimidine nucleotides. We present a divergent synthesis of pyrimidine and 8-oxo-purine nucleotides starting from a common prebiotic precursor that yields the β-ribo-stereochemistry found in the sugar phosphate backbone of biological nucleic acids. The generational relationship between pyrimidine and 8-oxo-purine nucleotides suggests that 8-oxo-purine ribonucleotides may have played a key role in primordial nucleic acids prior to the emergence of the canonical nucleotides of biology.

show abstract

Synthesis of Purine Cyclonucleoside Having a 8,2'-O-Anhydro Linkage

Cited by 21 publications

References 0 publications

Supramolecular Helices via Self-Assembly of 8-Oxoguanosines

Supramolecular Helices via Self-Assembly of 8-Oxoguanosines

The Conformation of Ribonucleosides in Solution. The Effect of Structure on the Orientation of the Base^*

Divergent prebiotic synthesis of pyrimidine and 8-oxo-purine ribonucleotides

Contact Info

Product

Resources

About

Synthesis of Purine Cyclonucleoside Having a 8,2'-O-Anhydro Linkage

Cited by 21 publications

References 0 publications

Supramolecular Helices via Self-Assembly of 8-Oxoguanosines

Supramolecular Helices via Self-Assembly of 8-Oxoguanosines

The Conformation of Ribonucleosides in Solution. The Effect of Structure on the Orientation of the Base*

Divergent prebiotic synthesis of pyrimidine and 8-oxo-purine ribonucleotides

Contact Info

Product

Resources

About

The Conformation of Ribonucleosides in Solution. The Effect of Structure on the Orientation of the Base^*