Phthaloyl Strategy—A New Approach Towards Oligodeoxyribonucleotide Synthesis

“…In this procedure, the nucleoside is persilylated using a silylating agent, and the acyl function is installed on the amino group using the corresponding acid chloride or acid anhydride. (3) Some acyl functions such as benzoyl, α‐phenylcinnamoyl, phthaloyl, and naphthaloyl are directly incorporated on the nucleobase using the corresponding acid chloride or anhydride (Beier & Pfleiderer, , ; Bhat et al, ; Karpeisky, Sweedler, Haeberli, Read, Jarvis, & Beigelman, ; Watanabe & Fox, ). (4) N ‐Lavulinyl derivatives of cytidine, adenosine, and guanosine were also prepared (Ogilvie, Nemer, Hakimelahi, Proba, & Lucas, ).…”

Section: Protection Of Exocyclic Amino Groupsmentioning

confidence: 99%

Nucleobase Protection of Deoxyribo‐ and Ribonucleosides

Meher

Iyer

2017

CP Nucleic Acid Chemistry

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Oligonucleotides carrying a variety of chemical modifications including conjugates are finding increasing applications in therapeutics, diagnostics, functional genomics, proteomics, and as research tools in chemical and molecular biology. The successful synthesis of oligonucleotides primarily depends on the use of appropriately protected nucleoside building blocks including the exocyclic amino groups of the nucleobases, the hydroxyl groups at the 2'-, 3'-, and 5'-positions of the sugar moieties, and the internucleotide phospho-linkage. This unit is a thoroughly revised update of the previously published version and describes the recent development of various protecting groups that facilitate reliable oligonucleotide synthesis. In addition, various protecting groups for the imide/lactam function of thymine/uracil and guanine, respectively, are described to prevent irreversible nucleobase modifications that may occur in the presence of reagents used in oligonucleotide synthesis. © 2017 by John Wiley & Sons, Inc.

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ChemInform Abstract: Phthaloyl Strategy — A New Approach Towards Oligodeoxyribonucleotide Synthesis.

Beier

Pfleiderer

1998

ChemInform

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Phthaloyl Strategy -A New Approach Towards Oligodeoxyribonucleotide Synthesis.-A new rapid strategy for the synthesis of the title compounds utilizing phthaloyl groups for protection of the heterocyclic amino function within the phosphoramidite approach is given. A large number of DNA-sequences in high purity and speed are synthesized. This strategy offers an excellent alternative to the common used acyl approach. -(BEIER, M.; PFLEIDERER, W.; Nucleosides Nucleotides 16 (1997) 7-9, 1621-1624; Fak.

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Phthaloyl Strategy—A New Approach Towards Oligodeoxyribonucleotide Synthesis

Cited by 3 publications

References 9 publications

Nucleotides, Part LXI, Phthaloyl Strategy: A New Concept of Oligonucleotide Synthesis

Nucleotides, Part LXI, Phthaloyl Strategy: A New Concept of Oligonucleotide Synthesis

Nucleobase Protection of Deoxyribo‐ and Ribonucleosides

ChemInform Abstract: Phthaloyl Strategy — A New Approach Towards Oligodeoxyribonucleotide Synthesis.

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