Improved Methods for 3′-O-Succinylation of 2′-Deoxyribo- and Ribonucleosides and Their Covalent Anchoring on Polymer Supports for Oligonucleotide Synthesis

Kumar, Pradeep; Ghosh, Narendra Nath; Sadana, Krishan L.; Garg, B. S.; Gupta, Kailash C.

doi:10.1080/07328319308019012

Cited by 27 publications

(17 citation statements)

References 21 publications

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“…Apart from the phosphoramidite, the silica-linked 8b was prepared. Succinylation of 7 [27] gave 8a (83 %), which was activated via the 4-nitrophenyl ester and linked to amino-functionalized Fractosil yielding 8b [28]. The ligand concentration was 72 pmol/g of solid support.…”

Section: Results Andmentioning

confidence: 99%

Oligodeoxyribonucleotides Containing 4‐Aminobenzimidazole in Place of Adenine: Solid‐phase synthesis and base pairing

Seela

Wenzel

1995

Helvetica Chimica Acta

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Oligonucleotides containing 4-aminobenzimidazole 2'-deoxyribofuranoside (1,3-dideaza-2'-deoxyadenosine; c'c3Ad, 1) were synthesized. For this purpose, various NH2-protecting groups were investigated, and the [(9H-fluoren-9-yl)methoxy]carbonyl group was selected for phosphoramidite protection (+ 4c). Apart from the phosphoramidite 3, the phosphonate 2 was prepared. Compound 1 was incorporated in a homooligonucleotide as well as in oligomers containing naturally occurring nucleosides. The T , values and the thermodynamic data of various duplexes (11 10, 17.10, 18.10) containing 4-aminobenzimidazole were determined. Although d [(c'c'A),,] (11) does not form a Hoogsteen duplex with d(T2,) (10) as observed with ~[(C'A),~], it destabilizes the Watson-Crick duplexes to a much smaller extent than it was expected from a bulged loop structure. Apparently, 4-aminobenzimidazole interacts with regular nucleoside residues within a Watson-Crick duplex structure, most likely by vertical stacking. According to the low basicity of the amino group, only weak H-bonding is expected.

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Section: Results Andmentioning

confidence: 99%

Oligodeoxyribonucleotides Containing 4‐Aminobenzimidazole in Place of Adenine: Solid‐phase synthesis and base pairing

Seela

Wenzel

1995

Helvetica Chimica Acta

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“…The succinylation of nucleosides has previously been optimised in solution, 38 with the reaction having been found to proceed very rapidly (10 min) in the presence of a catalytic amount of DMAP (0.5 eq) and succinic anhydride (1.5 eq) at 50 o C in 1,2-dichloroethane (DCE). Although the optimised milling procedure presented here required 30 min of milling with 1 eq of DMAP, this was achieved using 1.1 eq of succinic anhydride rather than 1.5 eq, which is the ratio that has previously been selected for optimised procedures.…”

Section: 3mentioning

confidence: 99%

“…Although the optimised milling procedure presented here required 30 min of milling with 1 eq of DMAP, this was achieved using 1.1 eq of succinic anhydride rather than 1.5 eq, which is the ratio that has previously been selected for optimised procedures. 36,38 Avoiding an excess of succinic anhydride allows for easier purification, and also opens up the possibility of a one-pot reaction with the next and effective stirring of the reactants. In contrast, the optimised procedure presented here was performed using only 6 eq of DCM ( Fig.…”

Section: 3mentioning

confidence: 99%

Applications of Mechanochemistry for the Synthesis of DNA on Ionic Liquid Supports

ohnston¹,

Hardacre²,

Migaud

2020

Preprint

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<p>The standard methodology for the synthesis of oligonucleotides is the solid-phase method. Here, we report the first case of mechanochemistry being directly applied to the synthesis of a dinucleotide on a soluble support. While mechanochemistry eliminates the need to solubilise a supported oligomer in solution phase for phosphoramidite coupling, the support still confers the benefit of being able to purify the product by precipitation, or by simple liquid-liquid extractions as needed. Furthermore, this study also explores the use of mechanochemistry in the initial functionalisation of the ionic liquid support with a nucleoside monomer.</p>

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“…The loading procedure gave DMTdC Ts support with a nucleoside content of 15 µmol/g. Recently several modified procedures for improved succinylation of nucleosides and their coupling to solid supports have been reported as well (36,37).…”

Section: The Concept Of Labelling Supportsmentioning

confidence: 99%

A New Method of Synthesis of Fluorescently Labelled Oligonucleotides and Their Application in DNA Sequencing

Markiewicz¹,

Gröger²,

Rösch³

et al. 1992

Nucleosides and Nucleotides

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Improved Methods for 3′-O-Succinylation of 2′-Deoxyribo- and Ribonucleosides and Their Covalent Anchoring on Polymer Supports for Oligonucleotide Synthesis

Cited by 27 publications

References 21 publications

Oligodeoxyribonucleotides Containing 4‐Aminobenzimidazole in Place of Adenine: Solid‐phase synthesis and base pairing

Oligodeoxyribonucleotides Containing 4‐Aminobenzimidazole in Place of Adenine: Solid‐phase synthesis and base pairing

Applications of Mechanochemistry for the Synthesis of DNA on Ionic Liquid Supports

A New Method of Synthesis of Fluorescently Labelled Oligonucleotides and Their Application in DNA Sequencing

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