An Improved Procedure for the Preparation of 8‐Substituted Guanines.

Xu, Ming; Giacomo, Fabio De; Paterson, Duncan E.; George, Tesmol G.; Vasella, Andrea

doi:10.1002/chin.200340161

Cited by 5 publications

(6 citation statements)

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“…Synthesis of 8mG : The required 8mG was synthesized from commercially available 6‐chloro‐2,4‐diaminopyrimidine in five steps that are described in detail in the SI. Firstly, 6‐(benzyloxy)‐5‐nitrosopyrimidine‐2,4‐diamine was synthesized in two steps utilizing a methodology developed by Pfleiderer et al42 Secondly, regioselective acylation followed by phosphorus(III)‐mediated cyclisation yielded the benzyl‐protected precursor 6‐(benzyloxy)‐8‐methyl‐9 H ‐purin‐2‐amine, as described by Xu et al43 Unfortunately, the procedure for the benzyl deprotection described by Xu et al provided the formate salt of 8mG, which was not of interest for this study. To obtain the pure 8mG, several deprotection strategies were tested and it was found that palladiumhydroxide (20% on carbon) with cyclohexene as hydrogen donor provided the desired compound 8mG in an acceptable 26% yield.…”

Section: Methodsmentioning

confidence: 99%

Control of Self‐Assembled 2D Nanostructures by Methylation of Guanine

Bald

Wang

Dong

et al. 2011

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Methylation of DNA nucleobases is an important control mechanism in biology applied, for example, in the regulation of gene expression. The effect of methylation on the intermolecular interactions between guanine molecules is studied through an interplay between scanning tunneling microscopy (STM) and density functional theory with empirical dispersion correction (DFT-D). The present STM and DFT-D results show that methylation of guanine can have subtle effects on the hydrogen-bond strength with a strong dependence on the position of methylation. It is demonstrated that the methylation of DNA nucleobases is a precise means to tune intermolecular interactions and consequently enables very specific recognition of DNA methylation by enzymes. This scheme is used to generate four different types of artificial 2D nanostructures from methylated guanine. For instance, a 2D guanine windmill motif that is stabilized by cooperative hydrogen bonding is revealed. It forms by self-assembly on a graphite surface under ambient conditions at the liquid-solid interface when the hydrogen-bonding donor at the N1 site of guanine is blocked by a methyl group.

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Section: Methodsmentioning

confidence: 99%

Control of Self‐Assembled 2D Nanostructures by Methylation of Guanine

Bald

Wang

Dong

et al. 2011

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“…17 OH as solvent also led to the formation of the corresponding n-octyl ether, but unlike the above cases, its purification from the solvent molecule, i.e., octyl alcohol, by distillation required an oil bath temperature higher than 125− 130 °C, namely, 145−150 °C. Consequently, the formation of n-octyl 2-(2,4-dioxopteridin-7-yl)benzimidazole-6-carboxylate 8 occurred as a result of hydrolysis.…”

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confidence: 97%

One-Pot Synthesis of 7-(Benzimidazol-2-yl)thioxolumazine and -lumazine Derivatives via H₂SO₄-Catalyzed Rearrangement of Quinoxalinones When Exposed to 5,6-Diamino-2-mercapto- and 2,5,6-Triaminopyrimidin-4-ols

et al. 2018

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A facile approach to a range of substituted 7-(benzimidazol-2-yl)thioxolumazines [7-(benzimidazol-2-yl)-2-thioxo-2,3-dihydropteridin-4(1H)-ones] and 7-(benzimidazol-2-yl)lumazines [7-(benzimidazol-2-yl)pteridine-2,4(1H,3H)-diones] is described. These new biheterocyclic systems are obtained via H2SO4-catalyzed rearrangement of quinoxalin-2-ones in the presence of 5,6-diamino-2-mercapto- and 2,5,6-triaminopyrimidin-4-ols. Thus, benzimidazole and pteridine rings are constructed in one synthetic step. A plausible ANRORC (addition of nucleophile, ring opening and ring closure)-type reaction mechanism is proposed. Applying the rearrangement to the aza-analogue of 3-benzoylquinoxalin-2(1H)-onei.e., 3-benzoylpyrido[2,3-b]pyrazin-2(1H)-onewith 5,6-diamino-2-mercaptopyrimidin-4-ol makes it possible to synthesize inaccessible 7-(1H-imidazo[4,5-b]pyridin-2-yl)-6-phenyl-2-thioxo-2,3-dihydropteridin-4(1H)-one. 7-(Benzimidazol-2-yl)-6-(2-fluorophenyl)-2-thioxo-2,3-dihydropteridin-4(1H)-ones undergoes intramolecular nucleophilic substitution of fluorine by a nitrogen of the benzimidazole fragment with the formation of benzo[4′,5′]imidazo[1′,2′:1,2]quinolino[4,3-g]pteridine-2,4(1H,3H)-diones as new heterocyclic systems.

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“…Accordingly, we had to incorporate a methylene group between the guanyl and mannosyl moieties and install the ether bond between the secondary C(3)-OH group of mannose and the C(6)-OH group of an allofuranose. Retrosynthetically ( Scheme 1 ), the ether bond could be formed by ring-opening cyclic sulfate 8 by the alkoxy anion corresponding to alcohol 7 [ 17 ], and the 8-substituted guanine could be formed by regioselective 4 -N- acylation of 2,4-diamino-5-nitrosopyrimidine 9 , followed by reductive cyclization, using a procedure developed by Vasella et al [ 18 ] .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a Pseudodisaccharide α-C-Glycosidically Linked to an 8-Alkylated Guanine

2013

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The synthesis of stable guanofosfocin analogues has attracted considerable attention in the past 15 years. Several guanofosfocin analogues mimicking the three constitutional elements of mannose, ribose, and guanine were designed and synthesized. Interest in ether-linked pseudodisaccharides and 8-alkylated guanines is increasing, due to their potential applications in life science. In this article, a novel guanofosfocin analogue 6, an ether-linked pseudodisaccharide connected α-C-glycosidically to an 8-alkylated guanine, was synthesized in a 10-longest linear step sequence from known diol 13, resulting in an overall yield of 26%. The key steps involve the ring-opening of cyclic sulfate 8 by alkoxide generated from 7 and a reductive cyclization of 4-N-acyl-2,4-diamino-5-nitrosopyrimidine 19 to form compound 6.

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An Improved Procedure for the Preparation of 8‐Substituted Guanines.

Cited by 5 publications

References 1 publication

Control of Self‐Assembled 2D Nanostructures by Methylation of Guanine

Control of Self‐Assembled 2D Nanostructures by Methylation of Guanine

One-Pot Synthesis of 7-(Benzimidazol-2-yl)thioxolumazine and -lumazine Derivatives via H₂SO₄-Catalyzed Rearrangement of Quinoxalinones When Exposed to 5,6-Diamino-2-mercapto- and 2,5,6-Triaminopyrimidin-4-ols

Synthesis of a Pseudodisaccharide α-C-Glycosidically Linked to an 8-Alkylated Guanine

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An Improved Procedure for the Preparation of 8‐Substituted Guanines.

Cited by 5 publications

References 1 publication

Control of Self‐Assembled 2D Nanostructures by Methylation of Guanine

Control of Self‐Assembled 2D Nanostructures by Methylation of Guanine

One-Pot Synthesis of 7-(Benzimidazol-2-yl)thioxolumazine and -lumazine Derivatives via H2SO4-Catalyzed Rearrangement of Quinoxalinones When Exposed to 5,6-Diamino-2-mercapto- and 2,5,6-Triaminopyrimidin-4-ols

Synthesis of a Pseudodisaccharide α-C-Glycosidically Linked to an 8-Alkylated Guanine

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One-Pot Synthesis of 7-(Benzimidazol-2-yl)thioxolumazine and -lumazine Derivatives via H₂SO₄-Catalyzed Rearrangement of Quinoxalinones When Exposed to 5,6-Diamino-2-mercapto- and 2,5,6-Triaminopyrimidin-4-ols