Oligonucleotide derivatives in nucleic acid hybridization analysis. III. Synthesis and investigation of properties of oligonucleotides, bearing bifunctional non-nucleotide insertion

Kupryushkin, Maxim S.; Pyshnyi, D. V.

doi:10.1134/s106816201206009x

Cited by 5 publications

(3 citation statements)

References 37 publications

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“…For example, propanediol-, , threoninol-, and serinol-based , phosphoramidites can be attached on a DNA strand, but their synthesis starts either with racemic mixtures or costly enantiopure diols. Other reports show the elegant synthesis and use of hydroxyprolinol- , and oxamide-based , phosphoramidites, but these may lead to stability issues during the final deprotection under basic conditions.…”

Section: Introductionmentioning

confidence: 59%

“…For example, propanediol-, 41,42 threoninol-, 43 and serinol-based 44,45 phosphoramidites can be attached on a DNA strand, but their synthesis starts either with racemic mixtures or costly enantiopure diols. Other reports show the elegant synthesis and use of hydroxyprolinol-46,47 and oxamide-based 48,49 phosphoramidites, but these may lead to stability issues during the final deprotection under basic conditions. In this manuscript, we explore the use of a tertiary amine scaffold to make a range of multifunctional DNA strands and sequence-controlled polymers via phosphoramidite synthesis.…”

Section: ■ Introductionmentioning

confidence: 99%

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Modular Strategy To Expand the Chemical Diversity of DNA and Sequence-Controlled Polymers

et al. 2018

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Sequence-defined polymers with customizable sequences, monodispersity, substantial length, and large chemical diversity are of great interest to mimic the efficiency and selectivity of biopolymers. We report an efficient, facile, and scalable synthetic route to introduce many chemical functionalities, such as amino acids and sugars in nucleic acids and sequence-controlled oligophosphodiesters. Through achiral tertiary amine molecules that are perfectly compatible with automated DNA synthesis, readily available amines or azides can be turned into phosphoramidites in two steps only. Individual attachment yields on nucleic acids and artificial oligophosphodiesters using automated solid-phase synthesis (SPS) were >90% in almost all cases. Using this method, multiple water-soluble sequence-defined oligomers bearing a range of functional groups in precise sequences could be synthesized and purified in high yields. The method described herein significantly expands the library of available functionalities for nucleic acids and sequence-controlled polymers.

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Section: Introductionmentioning

confidence: 59%

Section: ■ Introductionmentioning

confidence: 99%

Modular Strategy To Expand the Chemical Diversity of DNA and Sequence-Controlled Polymers

et al. 2018

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“…We describe herein a novel strategy for the design of nonnucleosidic phosphoramidites for nucleic acid functionalization, which is a merger of two approaches: one utilizing the ring-opening of lactones by aliphatic amines and another that uses activated oxalate esters for oligonucleotide derivatization . Also, it takes into account our previous experience in the synthesis and application of oligonucleotides with nonnucleosidic inserts …”

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confidence: 99%

Efficient Functionalization of Oligonucleotides by New Achiral Nonnucleosidic Monomers

et al. 2014

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A novel synthetic strategy has been designed for preparation of achiral nonnucleosidic phosphoramidite monomers for automated solid-phase oligonucleotide synthesis. It is based on O-DMTr-protected 4-(2-hydroxyethyl)-morpholine-2,3-dione as the key compound and a family of building blocks obtained by its ring-opening by primary aliphatic amines. A series of nonnucleosidic phosphoramidites containing various side-chain functionalities was synthesized, and corresponding oligodeoxyribonucleotides incorporating modified units in single or multiple positions along the chain were prepared.

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Oligonucleotide Functionalization by a Novel Alkyne-Modified Nonnucleosidic Reagent Obtained by Versatile Building Block Chemistry

Kupryushkin

Konevetz

Vasilyeva

et al. 2013

Nucleosides, Nucleotides and Nucleic Acids

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A convenient synthetic strategy has been designed to prepare an alkyne-modified synthon for automated DNA synthesis. It is based on the key O-DMTr-protected 4-(2-hydroxyethyl)morpholin-2,3-dione and building blocks obtained by its functionalization by various aliphatic amines. A respective nonnucleosidic phosphoramidite monomer containing a terminal alkyne in the side-chain was synthesized, and corresponding oligothymidylates incorporating the modification in various positions were prepared. The presence of the alkyne group was confirmed by Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) between the functionalized oligonucleotide and an azide derivative of 7-nitro-2,1,3-benzoxadiazole.

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Oligonucleotide derivatives in nucleic acid hybridization analysis. III. Synthesis and investigation of properties of oligonucleotides, bearing bifunctional non-nucleotide insertion

Cited by 5 publications

References 37 publications

Modular Strategy To Expand the Chemical Diversity of DNA and Sequence-Controlled Polymers

Modular Strategy To Expand the Chemical Diversity of DNA and Sequence-Controlled Polymers

Efficient Functionalization of Oligonucleotides by New Achiral Nonnucleosidic Monomers

Oligonucleotide Functionalization by a Novel Alkyne-Modified Nonnucleosidic Reagent Obtained by Versatile Building Block Chemistry

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