171284-48-3Relevant articles and documents
Synthesis of 13C- and 14C-labeled dinucleotide mRNA cap analogues for structural and biochemical studies
Piecyk, Karolina,Davis, Richard E.,Jankowska-Anyszka, Marzena
, p. 4391 - 4395 (2012)
Herein we describe the first simple and short method for specific labeling of mono- and trimethylated dinucleotide mRNA cap analogues with 13C and 14C isotopes. The labels were introduced within the cap structures either at the N7 for monomethylguanosine cap or N7 and N2 position for trimethylguanosine cap. The compounds designed for structural and biochemical studies will be useful tools for better understanding the role of the mRNA cap structures in pre-mRNA splicing, nucleocytoplasmic transport, translation initiation and mRNA degradation.
A convenient method for the preparation of N2,N2-dimethylguanosine
Avino,Mayordomo,Espuny,Bach,Eritja
, p. 1613 - 1617 (1995)
The preparation of N2,N2-dimethylguanosine is described. The use of the 2-(p-nitrophenyl)ethyl group instead of the benzyl protecting group for the O6 position of the guanine ring resulted in better yields and shorter protocols.
How to find the optimal partner - Studies of snurportin 1 interactions with U snRNA 5′ TMG-cap analogues containing modified 2-amino group of 7-methylguanosine
Piecyk, Karolina,Niedzwiecka, Anna,Ferenc-Mrozek, Aleksandra,Lukaszewicz, Maciej,Darzynkiewicz, Edward,Jankowska-Anyszka, Marzena
supporting information, p. 4660 - 4668 (2015/08/03)
Snurportin 1 is an adaptor protein that mediates the active nuclear import of uridine-rich small nuclear RNAs (U snRNA) by the importin-β receptor pathway. Its cellular activity influences the overall transport yield of small ribonucleoprotein complexes containing N2,N2,7-trimethylguanosine (TMG) capped U snRNA. So far little is still known about structural requirements related to molecular recognition of the trimethylguanosine moiety by snurportin in solution. Since these interactions are of a great biomedical importance, we synthesized a series of new 7-methylguanosine cap analogues with extended substituents at the exocyclic 2-amino group to gain a deeper insight into how the TMG-cap is adapted into the snurportin cap-binding pocket. Prepared chemical tools were applied in binding assays using emission spectroscopy. Surprisingly, our results revealed strict selectivity of snurportin towards the TMG-cap structure that relied mainly on its structural stiffness and compactness.
Synthesis of N2-modified 7-methylguanosine 5′- monophosphates as nematode translation inhibitors
Piecyk, Karolina,Davis, Richard E.,Jankowska-Anyszka, Marzena
experimental part, p. 4781 - 4789 (2012/08/29)
Preparative scale synthesis of 14 new N2-modified mononucleotide 5′ mRNA cap analogues was achieved. The key step involved use of an SNAr reaction with protected 2-fluoro inosine and various primary and secondary amines. The derivatives were tested in a parasitic nematode, Ascaris suum, cell-free system as translation inhibitors. The most effective compound with IC50 ～0.9 μM was a N2-p-metoxybenzyl-7- methylguanosine-5′-monophosphate 35.
A modified guanosine phosphoramidite for click functionalization of RNA on the sugar edge
Seidu-Larry, Salifu,Krieg, Bettina,Hirsch, Markus,Helm, Mark,Domingo, Olwen
supporting information, p. 11014 - 11016 (2013/01/15)
A propargyl containing guanosine phosphoramidite was synthesized and incorporated into siRNA, enabling click-ligation with an azido fluorophore onto the nucleobase sugar edge. Duplex stability was not affected by labeling at this new site, which allowed deconvolution of the effects of label, structure and attachment site on RNAi activity.
The Synthesis of 2′-O-[(Triisopropylsilyl)oxy] methyl (TOM) Phosphoramidites of Methylated Ribonucleosides (m1G, m2G, m22G, m1I, m3U, m4C, m6A, m62A) for Use in Automated RNA Solid-Phase Synthesis
Hoebartner, Claudia,Kreutz, Christoph,Flecker, Elke,Ottenschlaeger, Elke,Pils, Werner,Grubmayr, Karl,Micura, Ronald
, p. 851 - 873 (2007/10/03)
The straightforward synthesis of eight methylated ribonucleoside phosphoramidites is described. These building blocks allow for incorporation of the naturally occuring nucleosides 1-methylguanosine (m1G), N 2-methylguanosine (m2G), N2N 2-dimethylguanosine (m22G), 1-methylinosine (m1I), 3-methyluridine (m3U), N4- methylcytidine (m4C), N6-methyladenosine (m6A), and N6,N6-dimethyladenosine (m62A) into oligoribonucleotides by automated RNA solid-phase synthesis. In all cases, the ribose 2′-hydroxyl group of the building blocks is masked by the recently introduced [(triisopropylsilyl)oxy]methyl (TOM) group.
Efficient methods for the synthesis of [2-15N]guanosine and 2′-deoxy[2-15N]guanosine derivatives
Kamaike,Kinoshita,Niwa,Hirose,Suzuki,Ishido
, p. 59 - 75 (2007/10/03)
The nucleophilic addition-elimination reaction of 2′,3′, 5′-tri-O-acetyl-2-fluoro-O6-[2-(4-nitrophenyl)ethyl]inosine (8) with [15N]benzylamine in the presence of triethylamine afforded the N2-benzyl[2-15N]guanosine derivative (13) in a high yield, which was further convened into the N2-benzoyl[2-15N] guanosine derivative by treatment with ruthenium trichloride and tetrabutylammonium periodate. A similar sequence of reactions of 2′, 3′, 5′-tri-O-acetyl-2-fluoro-O6-[2-(methylthio)ethyl]inosine (9) and the 6-chloro-2-fluoro-9-(β-D-ribofuranosyl)-9H-purine derivative (11), which were respectively prepared from guanosine, with potassium [15N]phthalimide afforded the N2-phthaloyl [2-15N]guanosine derivative (15; 62%) and 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-chloro-2- [15N]phthalimido-9H-purine (17; 64%), respectively. Compounds 15 and 17 were then efficiently converted into 2′,3′,5′-tri-O-acetyl [2-15N]guanosine. The corresponding 2′-deoxy derivatives (16 and 18) were also synthesized through similar procedures.
The synthesis of RNA containing the modified nucleotides N2- methylguanosine and N6,N6-dimethyladenosine
Rife, Jason P.,Cheng, Charles S.,Moore, Peter B.,Strobel, Scott A.
, p. 2281 - 2288 (2007/10/03)
The phosphoramidites of the naturally occurring modified nucleotides N2-methylguanosine and N6, N6-dimethyladenosine were synthesized and incorporated into short oligoribonucleotides. Described are the syntheses of the phosphoramidites and the procedures used to deprotect oligoribonucleotides in which the O6 of m2G is protected with a 2-(p- nitrophenyl)ethyl group.
