2140-76-3Relevant articles and documents
A novel and economical synthesis of 2′-o-alkyl-uridines
Ross, Bruce S.,Springer, Robert H.,Tortorici, Zeb,Dimock, Stuart
, p. 1641 - 1643 (1997)
A highly efficient, two-step method to make 2′-O-methyluridine is described using only inexpensive reagents and no chromatography. The method is applicable for some other alkyls as well as some other pyrimidine derivatives. Copyright
SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS
-
, (2019/01/15)
This invention provides expressible polynucleotides, which can express a target protein or polypeptide. Synthetic mRNA constructs for producing a protein or polypeptide can contain one or more 5′ UTRs, where a 5′ UTR may be expressed by a gene of a plant. In some embodiments, a 5′ UTR may be expressed by a gene of a member of Arabidopsis genus. The synthetic mRNA constructs can be used as pharmaceutical agents for expressing a target protein or polypeptide in vivo.
Noncanonical RNA Nucleosides as Molecular Fossils of an Early Earth—Generation by Prebiotic Methylations and Carbamoylations
Schneider, Christina,Becker, Sidney,Okamura, Hidenori,Crisp, Antony,Amatov, Tynchtyk,Stadlmeier, Michael,Carell, Thomas
supporting information, p. 5943 - 5946 (2018/04/30)
The RNA-world hypothesis assumes that life on Earth started with small RNA molecules that catalyzed their own formation. Vital to this hypothesis is the need for prebiotic routes towards RNA. Contemporary RNA, however, is not only constructed from the four canonical nucleobases (A, C, G, and U), it also contains many chemically modified (noncanonical) bases. A still open question is whether these noncanonical bases were formed in parallel to the canonical bases (chemical origin) or later, when life demanded higher functional diversity (biological origin). Here we show that isocyanates in combination with sodium nitrite establish methylating and carbamoylating reactivity compatible with early Earth conditions. These reactions lead to the formation of methylated and amino acid modified nucleosides that are still extant. Our data provide a plausible scenario for the chemical origin of certain noncanonical bases, which suggests that they are fossils of an early Earth.
Regioselective Mitsunobu Reaction of Partially Protected Uridine
Szlenkier, Maurycy,Kamel, Karol,Boryski, Jerzy
, p. 410 - 425 (2016/08/05)
Mitsunobu reaction of partially acylated uridine proceeds with high regioselectivity for intramolecular SN2 anhydro linkage closuring. Under the reaction conditions, an isomeric mixture of diacyl uridine derivatives with either free 2′- or 3′-hydroxyl group was transformed into a single cyclonucleosidic product, 2,2′-anhydro-3′,5′-di-O-acyluridine. This paper presents a possible mechanism of the reactions, the explanation of observed phenomenon based on semiempirical and density functional theory (DFT) calculations and possible utility of this synthetic pathway.
A reliable Pd-mediated hydrogenolytic deprotection of BOM group of uridine ureido nitrogen
Aleiwi, Bilal A.,Kurosu, Michio
experimental part, p. 3758 - 3762 (2012/09/25)
The benzyloxymethyl (BOM) group has been utilized widely in syntheses of a variety of natural and non-natural products. The BOM group is also one of few choices to protect uridine ureido nitrogen. However, hydrogenolytic cleavage of the BOM group of uridine derivatives has been unreliably performed via heterogeneous conditions using Pd catalysts. One of the undesirable by-products formed by Pd-mediated hydrogenation conditions is the over-reduced product in which the C5-C6 double bond of the uracil moiety was saturated. To date, we have generated a wide range of uridine-containing antibacterial agents, where the BOM group has been utilized in their syntheses. In screening of deprotection conditions of the BOM group of uridine ureido nitrogen under Pd-mediated hydrogenation conditions, we realized that the addition of water to the iPrOH-based hydrogenation conditions can suppress the formation of over-reduced uridine derivatives and the addition of HCO2H (0.5%) dramatically improve the reaction rate. An optimized hydrogenation condition described here can be applicable to the BOM-deprotections of a wide range of uridine derivatives.
Synthesis and hybridization properties of 2′-O-methylated oligoribonucleotides incorporating 2′-O-naphthyluridines
Sekine, Mitsuo,Oeda, Yusuke,Iijima, Yoshihiro,Taguchi, Haruhiko,Ohkubo, Akihiro,Seio, Kohji
experimental part, p. 210 - 218 (2011/02/23)
2′-O-(1-Naphthyl)uridine and 2′-O-(2-naphthyl)uridine were synthesized by a microwave-mediated reaction of 2,2′-anhydrouridine with naphthols. Using the 3′-phosphoramidite building blocks, these 2′-O-aryluridine derivatives were incorporated into 2′-O-methylated oligoribonucleotides. Incorporation of five 2′-O-(2-naphthyl)uridines into a 2′-O-methylated RNA sense strand significantly increased the thermostability of the duplex with a 2′-O-methylated RNA antisense strand. Circular dichroism spectroscopy and molecular dynamic simulation of the duplexes formed between the modified RNAs and 2′-O-methyl RNAs suggested that there are π-π interactions between two neighboring naphthyl groups in a sequence of the five consecutively modified nucleosides.
Convenient RNA synthesis using a phosphoramidite possessing a biotinylated photocleavable group
Tomaya, Kota,Takahashi, Mayumi,Minakawa, Noriaki,Matsuda, Akira
body text, p. 3836 - 3839 (2010/11/17)
A convenient RNA synthesis using a biotin-streptavidin interaction and a photocleavable protecting group is described. The biotinylated photocleavable group was introduced at the 2′-position of the uridine derivative. Using the phosphoramidite 12, we attempted the synthesis of a 21mer RNA, which is pure enough to show potent RNAi activity compared with a conventionally prepared and HPLC-purified 21mer RNA with the same sequence.
Synthesis and solution conformation studies of the modified nucleoside N4,2′-O-dimethylcytidine (m4Cm) and its analogues
Mahto, Santosh K.,Chow, Christine S.
, p. 8795 - 8800 (2008/12/23)
The dimethylated ribosomal nucleoside m4Cm and its monomethylated analogues Cm and m4C were synthesized. The conformations (syn vs anti) of the three modified nucleosides and cytidine were determined by CD and 1D NOE difference spectroscopy. The ribose sugar puckers were determined by the use of proton coupling constants. The position of modification (e.g., O vs N methylation) was found to have an effect on the sugar pucker of cytidine.
Efficient large scale synthesis of 2′-O-alkyl pyrimidine ribonucleosides
Roy, Saroj K.,Tang, Jin-Yan
, p. 170 - 171 (2013/09/07)
An efficient process to synthesize 2′-O-alkyl pyrimidine ribonucleosides in high yield has been described. The inexpensive method was used on a multikilogram-scale synthesis and optimized reaction conditions have been investigated.
Introduction of 6-formylcytidine into a MYB binding sequence
Kittaka, Atsushi,Kuze, Tetsuya,Amano, Midori,Tanaka, Hiromichi,Miyasaka, Tadashi,Hirose, Kunihiko,Yoshida, Tadao,Sarai, Akinori,Yasukawa, Takashi,Ishii, Shunsuke
, p. 2769 - 2783 (2007/10/03)
Single 6-formylcytidine was introduced into a oligonucleotide duplex (23 mers) as a substitute for thymidine in the Myb binding sequence of 3'-TTGAC- 5'. The modified duplex showed Tm of 67 °C, which was six degrees lower than the Tm of the native duplex. Binding affinity of the 23-mers to the Myb protein was estimated by electrophoretic mobility shift assays, and the binding was almost completely abolished.
