Synthesis ofN2,N2, 7-trimethylguanosine cap derivatives

Iwase, Reiko; Sekine, Mitsuo; Tokumoto, Yuki; Ohshima, Yasumi; Hata, Tsujiaki

doi:10.1093/nar/17.22.8979

Cited by 12 publications

(7 citation statements)

References 15 publications

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“…The cap analogues ApppG and m 7 GpppG were purchased from Pharmacia. m 3 GpppG was synthesized and purified as described previously (Iwase et al ., 1989). Radiolabeled nucleotide triphosphates and [ 32 P]pCp were from Amersham.…”

Section: Methodsmentioning

confidence: 99%

Snurportin1, an m3G-cap-specific nuclear import receptor with a novel domain structure

Huber¹,

Cronshagen²,

Kadokura

et al. 1998

EMBO J

254

261

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The nuclear import of the spliceosomal snRNPs U1, U2, U4 and U5, is dependent on the presence of a complex nuclear localization signal (NLS). The latter is composed of the 5'-2,2,7-terminal trimethylguanosine (m3G) cap structure of the U snRNA and the Sm core domain. Here, we describe the isolation and cDNA cloning of a 45 kDa protein, termed snurportin1, which interacts specifically with m3G-cap but not m7G-cap structures. Snurportin1 enhances the m3G-capdependent nuclear import of U snRNPs in both Xenopus laevis oocytes and digitonin-permeabilized HeLa cells, demonstrating that it functions as an snRNP-specific nuclear import receptor. Interestingly, solely the m3G-cap and not the Sm core NLS appears to be recognized by snurportin1, indicating that at least two distinct import receptors interact with the complex snRNP NLS. Snurportin1 represents a novel nuclear import receptor which contains an N-terminal importin beta binding (IBB) domain, essential for function, and a C-terminal m3G-cap-binding region with no structural similarity to the arm repeat domain of importin alpha.

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Section: Methodsmentioning

confidence: 99%

Snurportin1, an m3G-cap-specific nuclear import receptor with a novel domain structure

Huber¹,

Cronshagen²,

Kadokura

et al. 1998

EMBO J

254

261

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“…AgOAc or Ag 2 NO 3 can also be used as activators. On synthesizing 7,N 2 ,N 2 -trimethylated cap-structures, the phenylthio activating group has been inserted in the monophosphate reactant 36 (Scheme 9b), and m 3 2,2,7 GpppA (8i) and m 3 2,2,7 GpppG (8g) have been obtained in 47 and 32 % yield by the reaction of 36 with ADP and GDP, respectively [64]. The nucleotide reactants are generally used as tetrabutylammonium salts to improve their solubility in organic solvents, and anhydrous pyridine is used as a solvent.…”

Section: Activation Using Phenylthio-and 4-methoxyphenylthio Groupsmentioning

confidence: 99%

“…The nucleotide reactants are generally used as tetrabutylammonium salts to improve their solubility in organic solvents, and anhydrous pyridine is used as a solvent. Even then nucleoside diphosphates may be poorly soluble, and in the case of GDP, DMF has been added to obtain a homogenous solution [64]. The disadvantage of the phenylthio method is that the synthesis of 35 results in a complicated product mixture, and the desired thiolate tends to decompose by hydrolysis of the N-glycosidic and P-S bonds during the ion-exchange purification required to isolate the product [63].…”

Section: Activation Using Phenylthio-and 4-methoxyphenylthio Groupsmentioning

confidence: 99%

Preparation and Properties of mRNA 5-cap Structure

Mikkola¹,

Salomaki²,

Zhang³

et al. 2005

COC

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The 5´-terminus of eukaryotic messenger RNA (mRNA) molecules contains an unique structure, viz. a dinucleoside 5´,5´-triphosphate moiety where the terminal nucleoside is 7-methylguanosine. This 5´-cap structure serves as a site of recognition for numerous enzymes involved in splicing, transport and translation of mRNA, and protects mRNA against intracellular exonucleases. In addition, viral RNA polymerases use capped mRNA sequences of the host cell as primers for viral RNA synthesis. Understanding of molecular mechanism of all these processes requires detailed information on the chemical properties of the cap structure, including capability to prepare conjugates and structural analogs of the cap for research tools. This review tends to summarize the present knowledge on various aspects of the chemistry of the cap structure, including chemical stability and mechanisms of breakdown, protolytic and complexing equilibria, stacking interactions and synthetic methodology.

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“…In our continuous studies − on the chemical synthesis of 2,2-dimethylguanosine- (m 2 2,2 G) and 2,2,7-trimethylguanosine-cap (m 2 2,2,7 G) structures which play an important role in transport of these capped RNAs between the cytoplasm and the nucleus in cells, , a variety of capping reagents to construct the cap structures at the 5‘-terminal site of oligoribonucleotides have been reported. − In an attempt to improve the solubility of capping reagents in organic solvents, we have used the lipophilic phenylboranylidene group as the protecting group for the 2‘,3‘- cis -diol function of m 2 2,2 G in the solid-phase synthesis of m 2 2,2 G-capped RNAs . However, this protecting group is so labile that in aqueous solution the cyclic phenylboronate ester linkages are easily hydrolyzed.…”

Section: Introductionmentioning

confidence: 99%

Chemically Stabilized Phenylboranylidene Groups Having a Dimethoxytrityl Group as a Colorimetrically Detectable Protecting Group Designed forcis-1,2-Diol Functions of Ribonucleosides in the Solid-Phase Synthesis of m₂^2,2G⁵^‘ppT

et al. 2005

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To not only improve the inherently poor stability of the phenylboranylidene group as a protecting group of the 2',3'-cis-diol function of ribonucleosides but also introduce a colorimetrically detectable function into its mother structure, various 2-[(dialkylamino)methyl]phenylboronic acid derivatives having a [(4,4'-dimethoxytrityl)oxy]methyl group were synthesized. The reaction of uridine with these substituted phenylboronic acid derivatives gave the corresponding 2',3'-O-phenylboranylideneuridine derivatives. The stability of these phenylboranylidene groups was examined. As a result, it was shown that the steric hindrance around the amino group greatly influenced the stability of the 2-substituted phenylboranylidene groups. The 2-aminomethyl-5-[[(4,4'-dimethoxytrityl)oxy]methyl]phenylboranylidene group was the most stable. Its 2-dimethylamino counterpart, the 2-[(dimethylamino)methyl]-5-[[(4,4'-dimethoxytrityl)oxy]methyl]phenylboranylidene group, was the second most stable. When the most and second stable protecting groups were applied to the synthesis of m(2)(2,2)G(5)(')ppT on controlled pore glass, the second stable protecting group showed the best result. The use of this DMTr-containing protecting group enabled us to estimate colorimetrically the amount of the m(2)(2,2)G residue that was incorporated into the reactive site of the pT-loaded CPG resin.

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Synthesis ofN²,N², 7-trimethylguanosine cap derivatives

Cited by 12 publications

References 15 publications

Snurportin1, an m3G-cap-specific nuclear import receptor with a novel domain structure

Snurportin1, an m3G-cap-specific nuclear import receptor with a novel domain structure

Preparation and Properties of mRNA 5-cap Structure

Chemically Stabilized Phenylboranylidene Groups Having a Dimethoxytrityl Group as a Colorimetrically Detectable Protecting Group Designed forcis-1,2-Diol Functions of Ribonucleosides in the Solid-Phase Synthesis of m₂^2,2G⁵^‘ppT

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Synthesis ofN2,N2, 7-trimethylguanosine cap derivatives

Cited by 12 publications

References 15 publications

Snurportin1, an m3G-cap-specific nuclear import receptor with a novel domain structure

Snurportin1, an m3G-cap-specific nuclear import receptor with a novel domain structure

Preparation and Properties of mRNA 5-cap Structure

Chemically Stabilized Phenylboranylidene Groups Having a Dimethoxytrityl Group as a Colorimetrically Detectable Protecting Group Designed forcis-1,2-Diol Functions of Ribonucleosides in the Solid-Phase Synthesis of m22,2G5‘ppT

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Synthesis ofN²,N², 7-trimethylguanosine cap derivatives

Chemically Stabilized Phenylboranylidene Groups Having a Dimethoxytrityl Group as a Colorimetrically Detectable Protecting Group Designed forcis-1,2-Diol Functions of Ribonucleosides in the Solid-Phase Synthesis of m₂^2,2G⁵^‘ppT