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

Milecki, Jan; Földesi, András; Fischer, Artur; Adamiak, Ryszard W.; Chattopadhyaya, J.

doi:10.1002/jlcr.503

Cited by 24 publications

(17 citation statements)

References 56 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[24][25][26] The nucleosidation reactions led, in both cases, to moderate yield of the adenine and thymine nucleoside analogues. [24][25][26] The nucleosidation reactions led, in both cases, to moderate yield of the adenine and thymine nucleoside analogues.…”

Section: Resultsmentioning

confidence: 96%

Synthesis of N-methyl-d-ribopyranuronamide nucleosides

2008

View full text Add to dashboard Cite

a b s t r a c tThe synthesis of N-methyl-D-ribopyranuronamide nucleosides is described. The key route is the rearrangement of a 1,2-O-isopropylidene protected furanose sugar with a carboxamide function in the 4-position to a ribopyranuronamide ring. The Lewis acid catalyzed condensation of adenine and thymine nucleobases with the per-O-acetylated N-methyl-D-ribopyranuronamide sugar is used to give the target nucleosides as a mixture of the a and b anomers. The mixture was separated and the final compounds were obtained by deacetylation in basic conditions.

show abstract

Section: Resultsmentioning

confidence: 96%

Synthesis of N-methyl-d-ribopyranuronamide nucleosides

2008

View full text Add to dashboard Cite

show abstract

“…Stirring compound 10 at room temperature in a 7N solution of ammonia in methanol for 2 days removed both the 2'-Oacetyl and the N(6)-benzoyl group to yield 16. Likewise, 11 was deprotected to the dideacetylated compound 17, which was selectively N-acylated to 18 with one equivalent of acetic anhydride in dimethylformamide [12].…”

Section: Chemical Synthesismentioning

confidence: 99%

Synthesis and antiviral evaluation of α-l-2′-deoxythreofuranosyl nucleosides

Toti

Derudas

McGuigan

et al. 2011

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

Th e syn t h e sis o f a series o f α-L-2'-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-α-Lthreose, involving a Vorbrüggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleoside phosphate prodrug of the T analogue, were evaluated against a broad panel of different viruses but found inactive, while also lacking notable cellular toxicity. The thymidine analogue showed inhibition to mitochondrial thymidine kinase-2 (TK-2), herpes simplex virus type 1 (HSV-1) TK, varicella-zoster virus (VZV) TK and M. tuberculosis thymidylate kinase.

show abstract

“…Acetylation of the nucleoside 2, followed by deisopropylidenation and finally by selective tritylation of the primary hydroxyl group gave compound 9 [41], which was then converted to the 4 0 -deoxy nucleoside analogue 11 via 4 0 -O-phenoxythiocarbonyl derivative 10 by the similar methodology as described above. Deacetylation of 11 was performed using NaOH/ethanol (EtOH)/pyridine [53] to afford compound 12, in good yield (88%). Oxidation of the free hydroxyl group in 2 0 -position of the sugar moiety of nucleoside 12 with PDC/Ac 2 O afforded the desired 2 0 -keto form, 1-(3,4-dideoxy-3-fluoro-6-O-trityl-b-D-glycero-hexopyranosyl-2-ulose)-N 4 -benzoyl cytosine (13a) in equilibrium with its hydrated analogue 13b in a 6:4 ratio, clearly determined by integration of the related 1 NMR signals.…”

Section: Chemistrymentioning

confidence: 99%

Dideoxy fluoro-ketopyranosyl nucleosides as potent antiviral agents: Synthesis and biological evaluation of 2,3- and 3,4-dideoxy-3-fluoro-4- and -2-keto-β-d-glucopyranosyl derivatives of N4-benzoyl cytosine

Manta

Tsoukala

Tzioumaki

et al. 2009

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

The synthesis of the dideoxy fluoro ketopyranonucleoside analogues, 1-(2,3-dideoxy-3-fluoro-6-O-trityl-beta-d-glycero-hexopyranosyl-4-ulose)-N(4)-benzoyl cytosine (7a), 1-(3,4-dideoxy-3-fluoro-6-O-trityl-beta-d-glycero-hexopyranosyl-2-ulose)-N(4)-benzoyl cytosine (13a) and their detritylated analogues 8a and 14a, respectively, is described. Condensation of peracetylated 3-deoxy-3-fluoro-D-glucopyranose (1) with silylated N(4)-benzoyl cytosine, followed by selective deprotection and isopropylidenation afforded compound 2. Routine deoxygenation at position 2', followed by a deprotection-selective reprotection sequence afforded the partially tritylated dideoxy nucleoside of cytosine 6, which upon oxidation of the free hydroxyl group at the 4'-position, furnished the desired tritylated 2,3-dideoxy-3-fluoro ketonucleoside 7a in equilibrium with its hydrated form 7b. Compound 2 was the starting material for the synthesis of the dideoxy fluoro ketopyranonucleoside 13a. Similarly, several subsequent protection and deprotection steps as well as routine deoxygenation at position 4', followed by oxidation of the free hydroxyl group at the 2'-position of the partially tritylated dideoxy nucleoside 12, yielded the desired carbonyl compound 13a in equilibrium with its hydrated form 13b. Finally, trityl removal from 7a/b and 13a/b provided the unprotected 2,3-dideoxy-3-fluoro-4-keto and 3,4-dideoxy-3-fluoro-2-ketopyranonucleoside analogues 8a and 14a, in equilibrium with their gem-diol forms 8b and 14b. None of the compounds showed inhibitory activity against a wide variety of DNA and RNA viruses at subtoxic concentrations, except 7a/b that was highly efficient against rotavirus infection. Nucleoside 7a/b also exhibited cytostatic activity against cells of various cancers. BrdU-cell cycle analysis revealed that the mechanism of cytostatic activity may be related to a delay in G1/S phase and initiation of programmed cell death.

show abstract

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

Cited by 24 publications

References 56 publications

Synthesis of N-methyl-d-ribopyranuronamide nucleosides

Synthesis of N-methyl-d-ribopyranuronamide nucleosides

Synthesis and antiviral evaluation of α-l-2′-deoxythreofuranosyl nucleosides

Dideoxy fluoro-ketopyranosyl nucleosides as potent antiviral agents: Synthesis and biological evaluation of 2,3- and 3,4-dideoxy-3-fluoro-4- and -2-keto-β-d-glucopyranosyl derivatives of N4-benzoyl cytosine

Contact Info

Product

Resources

About