Oligonucleotidic compounds. V. 2',3'-O-Alkylidene derivatives of ribonucleosides

Chládek, Stanislav; Smrt, J.

doi:10.1135/cccc19631301

Cited by 54 publications

(10 citation statements)

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“…A solution of 2',3'-O-isopropylideneuridine [38] (17.0 g; 59.8 mmol), 3,4-dihydro-2H-pyran (7.6 g; 8.2 ml; 90 mmol) and pyridinium p-toluenesulphonate (1.5 g; 6.0 mmol) in CH2C12 (150 ml) was stirred at ambient temperature for 1.5 h. The solution was washed with 5 % (w/v) NaHCO3 (2 x 50 ml) and saturated sodium chloride (50 ml), dried (MgSO4) and the solvent removed. The residue was purified by flash chromatography, elution with diethyl ether/petroleum ether (40-60 C) (1-2:1) followed by diethyl ether, which afforded 1 (16.7 g; 76%).…”

Section: '3'-o-isopropylidene-5'-o-tetrahydropyranyloxyuridine (1)mentioning

confidence: 99%

The roles of the conserved pyrimidine bases in hammerhead ribozyme catalysis: evidence for a magnesium ion-binding site

Murray

Adams

Arnold

et al. 1995

Biochemical Journal

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We report details of the synthesis and characterization of oligoribonucleotides containing 4-thiouridine or 2-pyrimidinone ribonucleoside (4HC). We have used these probes to examine the roles of the conserved pyrimidines in the central core of the hammerhead ribozyme. The effects on catalysis of singly-substituted hammerhead ribozyme and substrate strands were quantified in multiple-turnover reactions. Various effects were observed on kcat. and Km, with up to a 7-fold decrease and a 3-fold increase respectively. For substitutions with 4HC at positions 3 or 17, catalytic activity in single turnover reactions can be increased up to 8-fold equivalent to 40% of wild-type activity, by increasing the concentration of the Mg2+ cofactor, implying that these substitutions had a deleterious effect on Mg2+ binding. Calculations of the change in the apparent free energy of binding for variants at positions 3, 4 or 17 are each consistent with deletion of a single hydrogen-bond to an uncharged group in the ribozyme. The cytidine 5' to the scissile phosphate had not previously been thought to play a direct role in catalysis, however, removal of the exocyclic amino group decreased kcat. 4-fold. Recently, the crystal structures of a hammerhead ribozyme bound to either a non-cleavable 2'-deoxy substrate strand or a ribo-substrate strand have been reported. The kinetic properties of the variants described here are consistent with several key interactions seen in the crystals, in particular they provide experimental support for the assignment of the proposed catalytically active magnesium ion-binding site.

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Section: '3'-o-isopropylidene-5'-o-tetrahydropyranyloxyuridine (1)mentioning

confidence: 99%

The roles of the conserved pyrimidine bases in hammerhead ribozyme catalysis: evidence for a magnesium ion-binding site

Murray

Adams

Arnold

et al. 1995

Biochemical Journal

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“…A soln. of 19 [11] (869 mg, 2.68 mmol) in dry pyridine (13 ml) at 08 was treated with TsCl (842 mg, 4.42 mmol), allowed to warm to 258, stirred for 20 h, and evaporated. A soln.…”

Section: Experimental Partmentioning

confidence: 99%

“…To investigate their effect, we planned to synthesize the cyclohexylidene-Synthesis of the Uridine Intermediates. Tosylation of 2',3'-O-cyclohexylideneuridine (19) [11], followed by substitution with AcSK, afforded the thioacetate 20 (77%; Scheme 2). The analogous 2',3'-O-dimethyl derivative 25 was prepared via 2',3'-Odimethyluridine (24) [12] that was obtained from the 4-O-methyluridine (21) [12] by continuous addition over 2 d of excess CH 2 N 2 , followed by hydrolysis of the methoxyimino group at C(4) [12].…”

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confidence: 99%

Oligonucleotide Analogues with Integrated Bases and Backbones. Part 25

Bogliotti

Vasella

2010

Helvetica Chimica Acta

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The ability of A*[s]U dinucleosides to gel organic solvents and water is modulated by changing the nature of the substituents at OÀC(2') and OÀC(3'), as evidenced by comparing the gelation of the dinucleosides 7 -9 and the properties of the gels. A mere extension of the hydrophobic moiety, by replacing the isopropylidene groups of 2 by cyclohexylidene groups, as in 7, has a small effect, while changing the conformation of the ribose ring and reducing the size of the hydrophobic moiety, as in 8, has a strong effect on the scope of gelation, the minimum gelation concentration, as low as 0.07% for pentanol and decanol, and the properties of the gel. The fully deprotected dinucleoside 9 gels water at a minimal gelation concentration of 0.6%. A TEM of the corresponding xerogel shows the formation of fibers with a diameter of ca. 30 to 90 nm.

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“…Quantit ative formati on of ketals and acetals of nucleos ides have bden known (38). We have prepare d and charact erized the unlabel ed and 329-lab eled 5hydroxy pentana l monopho sphate using·t richlor oaceton itrile as the condens ing 1 1 reagent (39).…”

Section: Avian Myel Oblas Tosis Virus (Amv ) Bai Strainmentioning

confidence: 99%

Early steps in protein synthesis and their regulation: a background study related to the biological effects of radiation. Progress report, July 1, 1973--June 30, 1974

Zamecnik¹

1974

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Oligonucleotidic compounds. V. 2',3'-O-Alkylidene derivatives of ribonucleosides

Cited by 54 publications

References 0 publications

The roles of the conserved pyrimidine bases in hammerhead ribozyme catalysis: evidence for a magnesium ion-binding site

The roles of the conserved pyrimidine bases in hammerhead ribozyme catalysis: evidence for a magnesium ion-binding site

Oligonucleotide Analogues with Integrated Bases and Backbones. Part 25

Early steps in protein synthesis and their regulation: a background study related to the biological effects of radiation. Progress report, July 1, 1973--June 30, 1974

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