Synthesis of Aminoglycoside-Modified Oligonucleotides

Tona, Rolf; Bertolini, Reto; Hunziker, Jürg

doi:10.1021/ol005797d

Cited by 25 publications

(26 citation statements)

References 16 publications

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“…In Ref. 27, the base is coupled with 1,2,3,5-tetracetylribose. Since this method requires subsequent 2Ј-deoxygenation, we chose to glycosylate the silylated base with 2-deoxy-3,5-O-di-(toluoyl)-␣-D-erythro-pentafuranosylchloride (28).…”

Section: Inhibitor Synthesismentioning

confidence: 99%

Enzymatic and Structural Analysis of Inhibitors Designed against Mycobacterium tuberculosis Thymidylate Kinase

Haouz¹,

Vanheusden²,

Munier‐Lehmann³

et al. 2003

Journal of Biological Chemistry

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Section: Inhibitor Synthesismentioning

confidence: 99%

Enzymatic and Structural Analysis of Inhibitors Designed against Mycobacterium tuberculosis Thymidylate Kinase

Haouz¹,

Vanheusden²,

Munier‐Lehmann³

et al. 2003

Journal of Biological Chemistry

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“…Furthermore, the amino groups should not be exposed when the adjacent hydroxyl groups still bear acyl-type protection, since OfN-acyl migration may take place. Base-modified 2′-deoxyuridine phosphoramidites, conjugated with 2,6-diaminoglucose (28) and neomycine units (29) have been used for the synthesis of aminoglycoside-modified oligonucleotides. The aminoglycoside moieties have been capped with protecting group combinations, such as acetyl esters with trifluoroacetamides and trifluoroacetylesters with Boc-carbamates.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Aminoglycoside Conjugates of 2′-O-Methyl Oligoribonucleotides

Ketomäki

Virta

2008

Bioconjugate Chem.

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Aminoglycoside conjugates of 2'- O-methyl oligoribonucleotides have been synthesized entirely on a solid phase using conventional phosphoramidate chemistry. For this purpose, appropriately protected neamine-derived phosphoramidites, viz., 2-cyanoethyl [6,3',4'-tri- O-levulinoyl- N (1), N (3), N (2) (') , N (6) (') -tetra(trifluoroacetyl)neamine-5- O-ethyl] N,N-diisopropylphosphoramidite, 1, and 2-cyanoethyl [6,3',4',2'',3''-penta- O-levulinoyl- N (1), N (3), N (2) (') , N (6) (') -tetra(trifluoroacetyl) ribostamycin-5''-yl] N, N-diisopropylphosphoramidite, 2, have been prepared and attached via phosphodiester linkage to an appropriate 2'- O-methyl oligoribonucleotide. Levulinoyl esters are used to cap the hydroxyl groups of the aminoglycoside moieties, since they may be selectively removed prior to ammonolysis. In this manner, the potential O-->N acyl migration is excluded. Applicability of the strategy has been demonstrated by the synthesis of eight different aminoglycoside conjugates, in which 1 and 2 are attached directly to the 5'-end ( 6 and 10) or, alternatively, to an inserted non-nucleosidic hydroxyalkyl armed branching unit ( 3, 4, or 5), which results in intrachain conjugates ( 7- 9, 11- 13). The potential of these conjugates to act as a sequence-selective artificial nuclease has been studied.

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“…[15] We reasoned that CuAAC, the best known "click chemistry" transformation, [16] could also be a useful method for producing the ligation of aminoglycosides and oligonucleotides. CuAAC, specifically a 1,3-dipolar cycloaddition of azides and alkynes which produces a triazole ring, [17] has become an outstanding method in medicinal chemistry [18] and means of building new materials.…”

Section: Resultsmentioning

confidence: 99%