DNG cytidine: synthesis and binding properties of octameric guanidinium-linked deoxycytidine oligomer

Szabo, Istvan E.; Bruice, Thomas C.

doi:10.1016/j.bmc.2004.05.010

Cited by 26 publications

(18 citation statements)

References 38 publications

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“…15a The resulting TBS‐protected 5‐formyl‐2′‐deoxycytosine was benzoylated to give 2 . Cleavage of the TBS groups was achieved with HF in pyridine 18. When the latter reaction is carried out in EtOAc, the free nucleoside 3 precipitates and no further purification is needed.…”

Section: Resultsmentioning

confidence: 99%

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Improved Synthesis and Mutagenicity of Oligonucleotides Containing 5‐Hydroxymethylcytosine, 5‐Formylcytosine and 5‐Carboxylcytosine

Münzel¹,

Li²,

Stathis³

et al. 2011

Chemistry A European J

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5-Formylcytosine (fC or (5-CHO)dC) and 5-carboxylcytosine (caC or (5-COOH)dC) have recently been identified as constituents of mammalian DNA. The nucleosides are formed from 5-methylcytosine (mC or (5-Me)dC) via 5-hydroxymethylcytosine (hmC or (5-HOMe)dC) and are possible intermediates of an active DNA demethylation process. Here we show efficient syntheses of phosphoramidites which enable the synthesis of DNA strands containing these cytosine modifications based on Pd(0)-catalyzed functionalization of 5-iododeoxycytidine. The first crystal structure of fC reveals the existence of an intramolecular H-bond between the exocyclic amine and the formyl group, which controls the conformation of the formyl substituent. Using a newly designed in vitro mutagenicity assay we show that fC and caC are only marginally mutagenic, which is a prerequisite for the bases to function as epigenetic control units.

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Section: Resultsmentioning

confidence: 99%

“…Cleavage of the TBS groups was achieved with HF in pyridine. [18] When the latter reaction is carried out in EtOAc, the free nucleoside 3 precipitates and no further purification is needed. Finally, the 5'-hydroxyl group of compound 3 was protected with a DMT group and the 3'-hydroxyl group phosphitylated to give the final compound 4.…”

Section: Resultsmentioning

confidence: 99%

Improved Synthesis and Mutagenicity of Oligonucleotides Containing 5‐Hydroxymethylcytosine, 5‐Formylcytosine and 5‐Carboxylcytosine

Münzel¹,

Li²,

Stathis³

et al. 2011

Chemistry A European J

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show abstract

“…[6] However, the 2,3 -anhydro product cannot be obtained by heating with Et 3 N and EtOH. A stronger base DBU had to be used, which has a weak nucleophilic property, to produce 9.…”

Section: Resultsmentioning

confidence: 99%

Study on Disulfur-Backboned Nucleic Acids: Part 3. Efficient Synthesis of 3′,5′-Dithio-2′-Deoxyuridine and Deoxycytidine

Shang

Wang

Cheng

et al. 2008

Nucleosides, Nucleotides and Nucleic Acids

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A general method is described for synthesizing 3',5'-dithio-2'-deoxypyrimidine nucleosides 6 and 13 from normal 2'-deoxynucleosides. 2,3'-Anhydronucleosides 2 and 9 are applied as intermediates in the process to reverse the conformation of 3'-position on sugar rings. The intramolecular rings of 2,3'-anhydrothymidine and uridine are opened by thioacetic acid directly to produce 3'-S-acetyl-3'-thio-2'-deoxynucleosides 3 or 5. To cytidine, OH(-) ion exchange resin was used to open the ring and 2'-deoxycytidine 10 was obtained in which 3'-OH group is in threo-conformation. The 3'-OH is activated by MsCl, and then substituted by potassium thioacetate to form the S,S'-diacetyl-3',5'-dithio-2'-deoxycytidine 12. The acetyl groups in 3',5' position are removed rapidly by EtSNa in EtSH solution to afford the target molecules 6 and 13. The differences of synthetic routes between uridine and cytidine are also discusssed.

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“…Deoxyribonucleic guanidine homo-oligomeric sequences, consisting of trimeric and octameric thymidyl [100], octameric cytidyl [101] and trimeric 7-deazaguanidyl moieties ( 57 – 60 ) [102] and a mixed-base tetramer [103] and hexamer [104] ( 61 – 63 ) were synthesised using the same strategy as noted above for RNG synthesis (Fig. 25).…”

Section: Reviewmentioning

confidence: 99%

(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

Blanco¹,

Ortega‐Caballero²,

Fernández³

2010

Beilstein J. Org. Chem.

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SummaryOligosaccharides are currently recognised as having functions that influence the entire spectrum of cell activities. However, a distinct disadvantage of naturally occurring oligosaccharides is their metabolic instability in biological systems. Therefore, much effort has been spent in the past two decades on the development of feasible routes to carbohydrate mimetics which can compete with their O-glycosidic counterparts in cell surface adhesion, inhibit carbohydrate processing enzymes, and interfere in the biosynthesis of specific cell surface carbohydrates. Such oligosaccharide mimetics are potential therapeutic agents against HIV and other infections, against cancer, diabetes and other metabolic diseases. An efficient strategy to access this type of compounds is the replacement of the glycosidic linkage by amide or pseudoamide functions such as thiourea, urea and guanidine. In this review we summarise the advances over the last decade in the synthesis of oligosaccharide mimetics that possess amide and pseudoamide linkages, as well as studies focussing on their supramolecular and recognition properties.

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DNG cytidine: synthesis and binding properties of octameric guanidinium-linked deoxycytidine oligomer

Cited by 26 publications

References 38 publications

Improved Synthesis and Mutagenicity of Oligonucleotides Containing 5‐Hydroxymethylcytosine, 5‐Formylcytosine and 5‐Carboxylcytosine

Improved Synthesis and Mutagenicity of Oligonucleotides Containing 5‐Hydroxymethylcytosine, 5‐Formylcytosine and 5‐Carboxylcytosine

Study on Disulfur-Backboned Nucleic Acids: Part 3. Efficient Synthesis of 3′,5′-Dithio-2′-Deoxyuridine and Deoxycytidine

(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

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