The first example of sequence-specific non-uniformly 13C5 labelled RNA: Synthesis of the 29mer HIV-1 TAR RNA with 13C Relaxation Window

Milecki, Jan; Zamaratski, Edouard; Maltseva, Tatiana; Földesi, András; Adamiak, Ryszard W.; Chattopadhyaya, J.

doi:10.1016/s0040-4020(99)00294-x

Cited by 21 publications

(18 citation statements)

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“…Recently we have reported 34 the synthesis of ribonucleosides with [ 13 C 5 ]labelled ribose residues and introduced them into the TAR-RNA oligonucleotide at specifically chosen sites. The aim of the present study was to extend this approach to construct nucleoside building blocks, which are labelled with different isotopes in different residues of the molecule.…”

Section: Resultsmentioning

confidence: 99%

“…The [ 13 C 5 ]-labelled acylated ribose was prepared in 42% total yield starting from commercially available [ 13 C 6 ]-d-glucose via our earlier reported procedure. 34 The synthesis of the [6-15 N]-adenine aglycon was performed according to Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

“…The 1-O-acetyl-2,3,5-tri-O-toluoyl-b-d-[1,2,3,4,5-13 C 5 ]-ribofuranose for the synthesis of labelled nucleosides was synthesized according to our earlier procedure. 34 Methylene chloride, ethyl acetate, cyclohexane, hexane, acetone, methanol and ethanol were distilled prior to use. Triethylamine and N,N-diisopropylethylamine (DIPEA) were distilled from CaH 2 and stored over molecular sieves (4 ( A A).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of multiply labelled ribonucleosides for sequence‐specific labelling of oligo‐RNA

Milecki¹,

Földesi²,

Fischer³

et al. 2001

Labelled Comp Radiopharmac

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SummaryThe synthesis of ribonucleotide blocks multiply labelled with 2 H, 13 C and 15 N for solid support synthesis of sequence specifically labelled RNA is described. Labels were introduced in the ribose ring ( 13 C), C5 position of pyrimidine nucleobases ( 2 H) and exocyclic amino groups ( 15 N) and serve as multiple probes for studying the various physicochemical consequences of physiologically important RNA folding by high-resolution multi-nuclear NMR spectroscopy.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis of multiply labelled ribonucleosides for sequence‐specific labelling of oligo‐RNA

Milecki¹,

Földesi²,

Fischer³

et al. 2001

Labelled Comp Radiopharmac

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“…5 -O-(4,4 -dimethoxytrityl)uridine (6) was obtained according to Ref. [21] Melting points were determined on a Laboratory Devices Mel-Temp II micromelting points apparatus (Laboratory Devices, Holliston, MA, USA) and remain uncorrected. The NMR spectra were recorded on a Bruker Avance 400 MHz spectrometer in DMSO-d 6 with tetramethylsilane as an internal standard: chemical shifts are reported in δ-values (ppm) and coupling constants are given in Hz.…”

Section: Chemistrymentioning

confidence: 99%

Regioselective Mitsunobu Reaction of Partially Protected Uridine

Szlenkier

Kamel

Boryski

2016

Nucleosides, Nucleotides & Nucleic Acids

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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.

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“…One of the potential drawbacks of the uniform labelling technique is the possible overcrowding of the heterodomain of the spectra since these nuclei are NMR active. To avoid this, it is important to explore economically viable ways for the site-specific incorporation of the 13 C/ 15 N labelled monomer units to generate short uniformly isotope enriched stretches, separated by nonenriched stretches, in a DNA or a RNA molecule by chemical 26,27 or enzymatic means 28,29 , simply to disperse the signals optimally and to reduce overcrowding.…”

Section: Introductionmentioning

confidence: 99%