Improved synthesis of oligodeoxyribonucleotide using 3-methoxy-4-phenoxybenzoyl group for amino protection.

doi:10.1093/NAR/14.15.6197

Paper

Improved synthesis of oligodeoxyribonucleotide using 3-methoxy-4-phenoxybenzoyl group for amino protection.

Published Aug 11, 1986 · R. Mishra, K. Misra

Nucleic acids research

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11

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0

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Abstract

3-Methoxy-4-phenoxybenzoyl group has been used for the protection of exocyclic amino group of nucleosides. In case of 2'-deoxycytidine it has been found to be highly selective under controlled conditions. The N-protected derivatives of 2'-deoxyadenosine and 2'-deoxyguanosine have been found to be sufficiently stable towards acids minimising depurination under conditions of synthesis of oligodeoxyribonucleotide on solid support via phosphotriester approach. The high lipophilicity of the group and milder deprotection conditions are additional advantages.

Study Snapshot

3-Methoxy-4-phenoxybenzoyl group effectively protects exocyclic amino groups of nucleosides, resulting in stable, acid-resistant oligodeoxyribonucleotides for synthesis on solid support.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Improved synthesis of oligodeoxyribonucleotide using 3-methoxy-4-phenoxybenzoyl group for amino protection.

References

Citations

Nucleobase Protection of Deoxyribo‐ and Ribonucleosides

Protecting groups for nucleoside building blocks facilitate reliable oligonucleotide synthesis, preventing irreversible nucleobase modifications in various applications.

Synthesis and properties of nucleoside derivatives acylated by chemically stable 2-(trimethylsilyl)benzoyl group.

The study demonstrates the synthesis and properties of nucleoside derivatives acylated by 2-(trimethylsilyl)benzoyl, which is extremely stable under basic conditions when introduced into thymidine, deoxycytidine, and uridine.

Design and Synthesis of Some New α‐Phenyl Cinnamoyl Derivatives for Selective Protection of Purine Nucleosides

New phenylcinnamic acid derivatives effectively protect purine nucleosides, minimizing depurination and offering ease of syntheses and stability in acidic environments.

Polymer supported carbodiimide strategy for the synthesis of N-acylated derivatives of deoxy- and ribo purinenucleosides using active esters.

Polymer supported carbodiimide is a cost-effective and reusable strategy for selective protection of purine nucleosides, avoiding contamination with DCU and enabling the synthesis of N-acylated derivatives.

Nucleotide synthesis via methods without nucleoside-base protection.

N-unprotected methods simplify oligonucleotide synthesis, reducing steps and avoiding undesirable reagents, while extending the range of synthesizable artificial analogues with base-labile functions.