The Alkali-Stable Dinucleotide Sequences and the Chain Termini in Soluble Ribonucleates from Wheat Germ<sup>*</sup>

Hudson, Luke A.; Gray, Michael W.; Lane, B. G.

doi:10.1021/bi00886a015

Cited by 43 publications

(23 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…15,16 A 2′-O-methylpseudouridine derivative (Ψm) is found in 18S and 28S wheat embryo tRNAs and rRNAs. 17 In this study, a series of 3-subsitiuted uridine and pseudouridine analogues (acp 3 U, m 1 acp 3 Ψ, 3-(4-amino-4-carboxybutyl)uridine or acb 3 U, 3-(3-carboxypropyl)uridine or cp 3 U, 3-(4-hydroxybutyl)uridine or hb 3 U, and 1-methyl-3-(4-hydroxybutyl)pseudouridine or m 1 hb 3 Ψ, Figure 1) were prepared by using a Mitsunobu reaction in the key step, and their solution conformations were examined by using a variety of biophysical techniques, namely circular dichroism (CD) and NMR nuclear Overhauser effect (NOE) spectroscopy. The uridine analogue cp 3 U was synthesized and compared with acp 3 U to better understand the role of the homoserine amino group in influencing sugar/base conformation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and solution conformation studies of 3-substituted uridine and pseudouridine derivatives

Chang

Herath

Wang

et al. 2008

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

A series of 3-substituted uridine and pseudouridine derivatives, based on the naturally occurring 3-(3-amino-3-carboxypropyl) modification, were synthesized. Their aqueous solution conformations were determined by using circular dichroism and NMR spectroscopy. Functional group composition and chain length were shown to have only a subtle influence on the distribution of syn/anti conformations of the modified nucleosides. The dominating factor appears to be the glycosidic linkage (C-vs. N-glycoside) in determining the nucleoside conformation.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis and solution conformation studies of 3-substituted uridine and pseudouridine derivatives

Chang

Herath

Wang

et al. 2008

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

“…After 30-min incubation 32P, (specific activity 0.46 mCi/Amol; 3.3 ,gCi/ml) was added and the cells were incubated 30 min more. After cell lysis and RNA extraction, the newly synthesized, labeled tRNA was purified by fractional precipitation with cetyltrimethylammonium bromide (13). Each preparation gave a single peak of label, at the tRNA position, upon gel electrophoretic analysis.…”

Section: Resultsmentioning

confidence: 99%

“…Each preparation gave a single peak of label, at the tRNA position, upon gel electrophoretic analysis. The tRNA was hydrolyzed to 5' nucleotides with highly purified snake venom phosphodiesterase (13), and the nucleotides were separated by two-dimensional paper chromatography. Modified nucleotides were identified by comigration with authentic marker nucleotides and quantitated by measuring the radioactivities of excised spots in toluene-based scintillant.…”

Section: Resultsmentioning

confidence: 99%

Methionine analogs and cell division regulation in the yeast Saccharomyces cerevisiae.

Singer¹,

Johnston²,

Bedard³

1978

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

Methionine analogs such as ethionine, selenomethionine, and trifluoromethionine all arrest growth and division of the yeast Saceharomyces cerevisiae. One analog, ethionine, caused cells of the yeast to arrest specifically within GI; reciprocal shift experiments showed that ethionine and a-factor arrested cells at the same step ("start") The major effect of ethionine on synthesis of macromolecules was to reduce both the rate of appearance of 35S ribosomal precursor RNA and the rate of production of mature rRNA. Synthesis of protein was relatively unaffected by ethionine. Selenomethionine and trifluoromethionine caused cells to arrest randomly in the cell division cycle. Although treatment of cells with either selenomethionine or trifluoromethionine also reduced the rate of total RNA synthesis, each of these analogs had other effects that presumably prohibited completion of the cell cycle. We propose that the rate of rRNA production is an important regulatory event in the cell cycle.The yeast Saccharomyces cerevisiae, like most eukaryotic cells, regulates its division in the GI portion of the cell cycle. A temperature-sensitive mutant (cdc 28) affected in the ability to progress through Gi and the mating pheromone a-factor have been used to define a period within Gi called "start" (1). The performance of start results in the initiation of both budding and deoxyribonucleic acid (DNA) synthesis. Before the start event can be completed, many physiological requirements must be met. Starvation for required nutrients causes cells of S. cerevtsiae to arrest in GI prior to completion of start.Recently, Unger and Hartwell (2) demonstrated that starvation for sulfate caused yeast cells to arrest at a defined point in Gi. Moreover, they demonstrated that depriving methionine auxotrophs of methionine, or incubating a strain conditionally defective in methionyl-tRNA synthetase at the nonpermissive temperature, also caused cells to accumulate within Gi. We have further examined the molecular basis for GI regulation by determining the effects of methionine analogs on growth and cell division. We have used three analogs-L-ethionine, DL-selenomethionine, and L-trifluoromethionine-all of which have been shown (3) to have similar effects on methionine metabolism. All three analogs repress endogenous methionine biosynthesis, may be esterified both in vitro and in dvo to tRNA, and may be incorporated into protein.We have found that one of these analogs, ethionine, causes cells to accumulate rapidly in Gi. Selenomethionine and trifluoromethionine, on the other hand, cause cells to arrest randomly in the cell division cycle. We report here our investigations into the molecular alterations correlated with the ethionine-mediated GI arrest.The publication costs of this article were defrayed in part by page charge payment. This article must therefore be hereby marked "advertisement" in accordance with 18 U. S. C. §1734 solely to indicate this fact. 6083MATERIALS AND METHODS Strains and Media. The diploid strain S. cerevisiae AG1-7 (...

show abstract

“…(3 ml) was added dropwise to a soln. of N6-[2-(4-nitrophenyl)ethoxycarbonyl]adenosine (17) [61] [63] (463 mg, 1.0 mmol) in DMF (30 ml) at 0". After stirring for 30 h at 0".…”

Section: '-O-melhyi-5'-o-(monnmethnxytri~ylj-n6-[2-(4-nitrophenyl)~tmentioning

confidence: 99%

Nucleosides. Part LXI. A Simple Procedure for the Monomethylation of Protected and Unprotected Ribonucleosides in the 2′‐O‐ and 3′‐O‐Position Using Diazomethane and the Catalyst Stannous Chloride

Cramer

Pfleiderer

1996

Helvetica Chimica Acta

View full text Add to dashboard Cite

Intensive studies on the diazomethane methylation of the common rihonucleosides uridine, cytidine, adenosine, and guanosine and its derivatives were performed to obtain preferentially the 2'-0 -methyl isomers, Methylation of 5'-O-(monomethoxytrityl)-N2-[2-(4-nitrophenyl)ethoxycarbonyl]-O6-[2-(4-nitrophenyl)ethyl]-guanosine (1) with diazomethane resulted in an almost quantitative yield of the 2'-and 3'W-methyl isomers which could be separated by simple silica-gel flash chromatography (Schemr I ) . Adenosine, cytidine, and uridine were methylated with diazomethane with and without protection of the 5'-O-position by a mono-or dimethoxytrityl group and the aglycone moiety of adenosine and cytidine by the 2-(4-nitrophenyl)ethoxycarhonyl (npeoc) group (Schemes 2-4). Attempts to increase the formation of the 2-0-methyl isomer as much as possible were based upon various solvents, temperatures, catalysts, and concentration of the catalysts during the methylation reaction.

show abstract

The Alkali-Stable Dinucleotide Sequences and the Chain Termini in Soluble Ribonucleates from Wheat Germ^*

Cited by 43 publications

References 15 publications

Synthesis and solution conformation studies of 3-substituted uridine and pseudouridine derivatives

Synthesis and solution conformation studies of 3-substituted uridine and pseudouridine derivatives

Methionine analogs and cell division regulation in the yeast Saccharomyces cerevisiae.

Nucleosides. Part LXI. A Simple Procedure for the Monomethylation of Protected and Unprotected Ribonucleosides in the 2′‐O‐ and 3′‐O‐Position Using Diazomethane and the Catalyst Stannous Chloride

Contact Info

Product

Resources

About

The Alkali-Stable Dinucleotide Sequences and the Chain Termini in Soluble Ribonucleates from Wheat Germ*

Cited by 43 publications

References 15 publications

Synthesis and solution conformation studies of 3-substituted uridine and pseudouridine derivatives

Synthesis and solution conformation studies of 3-substituted uridine and pseudouridine derivatives

Methionine analogs and cell division regulation in the yeast Saccharomyces cerevisiae.

Nucleosides. Part LXI. A Simple Procedure for the Monomethylation of Protected and Unprotected Ribonucleosides in the 2′‐O‐ and 3′‐O‐Position Using Diazomethane and the Catalyst Stannous Chloride

Contact Info

Product

Resources

About

The Alkali-Stable Dinucleotide Sequences and the Chain Termini in Soluble Ribonucleates from Wheat Germ^*