Facile preparation of C-glycosylbarbiturates and C-glycosylbarbituric acids

Gonzalez, Martin Avalos; Requejo, Jose L. Jimenez; Albarran, Juan C. Palacios; Perez, Juan A. Gabis

doi:10.1016/0008-6215(86)84005-8

Cited by 55 publications

(26 citation statements)

References 25 publications

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“…It is more likely that this reaction takes place at the 5-carbon (Gonzales et al 1986) Unlike AUGC, the transparency of urazole and guanazole in the ultraviolet would result in nucleic acids containing these bases being protected from ultraviolet degradation on the early Earth. The ultraviolet flux at the Earth's surface is thought to have been much higher than at present because of the absence of an ozone layer.…”

Section: Discussionmentioning

confidence: 99%

Alternative bases in the RNA world: The prebiotic synthesis of urazole and its ribosides

1994

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We have prepared a [32P]-labled oligonucleotide probe carrying a free primary amine at its 3'-terminus. This probe is used to initiate polymerization of aziridine (ethyleneimine) in aqueous solution. The nature of the oligomeric products and the kinetics of their formation are then monitored by gel electrophoresis. Our results are generally consistent with those obtained using conventional techniques. We have also investigated the effect of polyanionic templates on the rate of oligomerization of aziridine. We find that water-soluble polyanions generally accelerate the polymerization. The sodium salt of polymethacrylic acid is the most effective of the templates that we studied. The methods introduced in this paper should be applicable to a variety of polymerization reactions in aqueous solution. They should greatly simplify the screening of potentially prebiotic polymerization reactions.

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Section: Discussionmentioning

confidence: 99%

Alternative bases in the RNA world: The prebiotic synthesis of urazole and its ribosides

1994

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“…reported reactions between aldosesa nd barbiturica cids in basic aqueous media, affording b-C-glycosyl barbiturates. [213] The cyclization of the a,b-unsaturated intermediate leaves an egative chargea tt he C-5 of the barbiturate moiety.T hat fact was used by Critchley et al to carry out alky-lation at that positionb ym eans of nucleophilic aromatic substitutionw itha llyl and benzyl halides (Scheme57). They have also shown that the barbiturate moiety can be hydrolyzed, [206] Scheme53.…”

Section: Knoevenagel Condensationmentioning

confidence: 99%

Chemoselective Reactions for the Synthesis of Glycoconjugates from Unprotected Carbohydrates

et al. 2017

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Glycobiology is the comprehensive biological investigation of carbohydrates. The study of the role and function of complex carbohydrates often requires the attachment of carbohydrates to surfaces, their tagging with fluorophores, or their conversion into natural or non-natural glycoconjugates, such as glycopeptides or glycolipids. Glycobiology and its "omics", glycomics, require easy and robust chemical methods for the construction of these glycoconjugates. This review gives an overview of the rapidly expanding field of chemical reactions that selectively convert unprotected carbohydrates into glycoconjugates through the anomeric position. The discussion is divided in terms of the anomeric bond type of the newly formed glycoconjugates, including O-, N-, S-, and C-glycosides.

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“…Starting from free D-mannose, reaction of the masked aldehyde function with pyrimidine derivatives [225] or 1,3-dimethylbarbituric acid [226][227][228] followed by heating, directly gave the desired b-C-mannopyranosides (Scheme 75).…”

Section: Intramolecular Reaction Between An Alcohol and An Unsaturatementioning

confidence: 99%

The synthesis of d-C-mannopyranosides

Choumane¹,

Banchet²,

Probst³

et al. 2010

Comptes Rendus. Chimie

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Facile preparation of C-glycosylbarbiturates and C-glycosylbarbituric acids

Cited by 55 publications

References 25 publications

Alternative bases in the RNA world: The prebiotic synthesis of urazole and its ribosides

Alternative bases in the RNA world: The prebiotic synthesis of urazole and its ribosides

Chemoselective Reactions for the Synthesis of Glycoconjugates from Unprotected Carbohydrates

The synthesis of d-C-mannopyranosides

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