Publication

Reliable chemical synthesis of oligoribonucleotides (RNA) with 2'-O-[(triisopropylsilyl)oxy]methyl(2'-O-tom)-protected phosphoramidites

2001
Journal Articles

Abstract

A method for the introduction of the 2'-O-[(triisopropylsilyl)oxy]methyl (=tom) group into N-acetylated, 5'-O-dimethoxytritylated ribonucleosides is presented. The corresponding 2'-O-tom-protected phosphoramidite building blocks were obtained in pure form and were successfully employed for the routine synthesis of oligoribonucleotides on DNA synthesizers. Under DNA coupling conditions (2.5 min coupling time for a 1.5-mmol synthesis scale) and with 5-(benzylthio)-1H-tetrazole (BTT) as activator. 2'-O-tom-protected phosphoramidites exhibited av. coupling yields >99.4%. The combination of N-acetyl and 2'-O-tom protecting groups allowed a reliable and complete two-step deprotection, first with MeNH2 in EtOH/H2O and then with Bu4NF in THF, without concomitant destruction of the product RNA sequences. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/fee8cc24-dc8a-4f64-809d-a2ed43e686ba

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2001
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/fee8cc24-dc8a-4f64-809d-a2ed43e686ba

About this result

Related concepts (20)

Oligonucleotide synthesis

Oligonucleotide synthesis is the chemical synthesis of relatively short fragments of nucleic acids with defined chemical structure (sequence). The technique is extremely useful in current laboratory practice because it provides a rapid and inexpensive access to custom-made oligonucleotides of the desired sequence. Whereas enzymes synthesize DNA and RNA only in a 5' to 3' direction, chemical oligonucleotide synthesis does not have this limitation, although it is most often carried out in the opposite, 3' to 5' direction.

Protecting group

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In many preparations of delicate organic compounds, some specific parts of their molecules cannot survive the required reagents or chemical environments. Then, these parts, or groups, must be protected. For example, lithium aluminium hydride is a highly reactive but useful reagent capable of reducing esters to alcohols.

Peptide synthesis

In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl group of one amino acid to the amino group of another. Protecting group strategies are usually necessary to prevent undesirable side reactions with the various amino acid side chains. Chemical peptide synthesis most commonly starts at the carboxyl end of the peptide (C-terminus), and proceeds toward the amino-terminus (N-terminus).