Oligonucleotides with 2′-O-carboxymethyl group: synthesis and 2′-conjugation via amide bond formation on solid phase

Kachalova, Anna V.; Zubin, E. M.; Stetsenko, Dmitry A.; Gait, Michael J.; Oretskaya, Tatiana S.

doi:10.1039/b409496d

Cited by 29 publications

(20 citation statements)

References 21 publications

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“…Basic hydrolysis of these esters is frequently plagued by low yields, long reaction times, the need for large excesses of reagents, and the formation of by-products that are difficult to separate [45][46][47].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Functionalised Nucleosides for Incorporation into Nucleic Acid-Based Serine Protease Mimics

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2007

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Section: Resultsmentioning

confidence: 99%

Synthesis of Functionalised Nucleosides for Incorporation into Nucleic Acid-Based Serine Protease Mimics

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2007

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“…11 3 Pivaloyloxymethyl 3´,5´ О (tetraisopropyldisiloxan 1,3 diyl)uridine (2) was obtained by known procedure. 15 The yield of compound 2 as a white foam was 70%, R f 0.34 (CHCl 3 -EtOH, 96 : 4 v/v). 1 2´ О Benzyloxycarbonylmethyl 3 pivaloyloxymethyl 3´,5´ О (tetraisopropyldisiloxan 1,3 diyl)uridine (3).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of oligo-2′-O-methylribonucleotides containing α-amino acid residues in 2′-position

et al. 2007

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Oligo 2´ O methylribonucleotides containing residues of phenylalanine, histidine, and lysine amides were synthesized with the use of new phosphoramidites of 2´ aminoacid deriva tives of uridine.Derivatives of oligonucleotides are widely used in mo lecular biology and medicine due to their unique ability to bind to complementary sequences of DNA and RNA, which can result in a selective suppression of expression of certain genes. At present, an intensive research work is being carried out aimed at the design of effective thera peutic preparations based on nucleic acids. 2, 3 Elaboration of methods for the synthesis of artificial ribonucleases is one of trends in chemistry of nucleic acids. 4,5 A cell or viral RNA may serve as the potential targets, which determines the topicality of this task in the first place. Very often, in the design of artificial ribo nucleases it is preferable to combine, in one molecule, an oligonucleotide complementary to the given region of RNA and a substance that catalyzes hydrolysis of certain phosphodiester bonds of the ribonucleic acid after forma tion of a two stranded complex (duplex). For example, attempts were undertaken at constructing artificial ribo nucleases based on oligonucleotides containing imidazole and primary aliphatic amine residues. 5, 6 It was shown earlier that in the presence of basic amino acids and short peptides containing polyamine residues a remarkable increase in the rate of cleavage of the RNA target takes place upon its treatment with ribozymes un der deficiency in magnesium ions. 7 In this connection, it can be supposed that oligonucleotides bearing basic amino acid residues can also possess ribonuclease activity. Thus, the development of efficient methods for the synthesis of amino acid derivatives of oligonucleotides is quite justi fied. The heterocyclic bases in the catalytic sites of ribozymes are often involved into various non covalent interactions essential for maintaining their structure and catalytic activity; the ribose residue, in particular its 2´ position, seems to be the most preferable for the modi fication. In the present work, a promising method of 2´ functionalization was used, which is based on the for mation of a carbamate bond between primary or second ary alcohol and primary aliphatic amine upon treatment with N,N´ carbonyldiimidazole 8 or N,N´ disuccinimidyl carbonate (DSC). 9 It was noted 8,9 that oligonucleotide derivatives containing N substituted carbamate bonds with involvment of the 2´ hydroxy group of uridine form duplexes with complementary DNA or RNA; these du plexes have low thermal stability. At the same time, it is known that many 2´ О alkyl derivatives of oligoribo nucleotides form particularly stable duplexes with comple mentary RNAs. 10 For example, it was shown 11 that analo gous 2´ derivatives do not decrease stability of the com plex of modified oligonucleotide with complementary RNA. In order to avoid the negative effect of the modifi cation on the hybridization properties of oligonucleotides, we have developed an ...

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“…The phosphoramidite is now commercially available from major suppliers, such as 5′-carboxy-modifier C5. Later, the method was optimized for the synthesis of 2′-conjugates through the formation of amide bonds either on the solid phase or in solution [ 297 , 298 ].…”

Section: Post-synthetic Conjugation Approachesmentioning

confidence: 99%

Chemistry of Peptide-Oligonucleotide Conjugates: A Review

2021

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Peptide-oligonucleotide conjugates (POCs) represent one of the increasingly successful albeit costly approaches to increasing the cellular uptake, tissue delivery, bioavailability, and, thus, overall efficiency of therapeutic nucleic acids, such as, antisense oligonucleotides and small interfering RNAs. This review puts the subject of chemical synthesis of POCs into the wider context of therapeutic oligonucleotides and the problem of nucleic acid drug delivery, cell-penetrating peptide structural types, the mechanisms of their intracellular transport, and the ways of application, which include the formation of non-covalent complexes with oligonucleotides (peptide additives) or covalent conjugation. The main strategies for the synthesis of POCs are viewed in detail, which are conceptually divided into (a) the stepwise solid-phase synthesis approach and (b) post-synthetic conjugation either in solution or on the solid phase, especially by means of various click chemistries. The relative advantages and disadvantages of both strategies are discussed and compared.

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Oligonucleotides with 2′-O-carboxymethyl group: synthesis and 2′-conjugation via amide bond formation on solid phase

Cited by 29 publications

References 21 publications

Synthesis of Functionalised Nucleosides for Incorporation into Nucleic Acid-Based Serine Protease Mimics

Synthesis of Functionalised Nucleosides for Incorporation into Nucleic Acid-Based Serine Protease Mimics

Synthesis of oligo-2′-O-methylribonucleotides containing α-amino acid residues in 2′-position

Chemistry of Peptide-Oligonucleotide Conjugates: A Review

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