Synthesis of 4′-methoxy 2′-deoxynucleoside phosphoramidites for incorporation into oligonucleotides

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F16%3A00469801" target="_blank" >RIV/61388963:_____/16:00469801 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1002/cpnc.15" target="_blank" >http://dx.doi.org/10.1002/cpnc.15</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/cpnc.15" target="_blank" >10.1002/cpnc.15</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of 4′-methoxy 2′-deoxynucleoside phosphoramidites for incorporation into oligonucleotides

Popis výsledku v původním jazyce

This unit contains detailed synthetic protocols for the preparation of 4′-methoxy 2′-deoxynucleoside phosphoramidite monomers for A, G, C, T, and U. First, 3′-silyl-protected 2′-deoxynucleosides (dNs) are converted in two steps to 4′,5′-enol acetates as the key starting compounds. Next, 4′-methoxy dNs are prepared by a one-pot procedure comprising N-iodosuccinimide-promoted methoxylation, hydrolysis, and reduction of the formed intermediates. Finally, 3′-phosphoramidites of 4′-methoxy dNs are obtained by a routine three-step procedure. Title phosphoramidite monomers are suitable for the synthesis of oligonucleotides on solid phase according to conventional amidite chemistry. 4′-Methoxy substitution represents a simple modification of the sugar part of dNs, where beta-D-erythro epimers preferentially adopt N-type (C3′-endo, RNA-like) conformation. Moreover, it imparts superior chemical stability, nuclease resistance, and excellent hybridization properties to modified 4′-methoxyoligodeoxynucleotides. The strong tendency toward RNA-selective hybridization suggests its potential utilization in antisense and/or RNAi technologies.

Název v anglickém jazyce

Synthesis of 4′-methoxy 2′-deoxynucleoside phosphoramidites for incorporation into oligonucleotides

Popis výsledku anglicky

This unit contains detailed synthetic protocols for the preparation of 4′-methoxy 2′-deoxynucleoside phosphoramidite monomers for A, G, C, T, and U. First, 3′-silyl-protected 2′-deoxynucleosides (dNs) are converted in two steps to 4′,5′-enol acetates as the key starting compounds. Next, 4′-methoxy dNs are prepared by a one-pot procedure comprising N-iodosuccinimide-promoted methoxylation, hydrolysis, and reduction of the formed intermediates. Finally, 3′-phosphoramidites of 4′-methoxy dNs are obtained by a routine three-step procedure. Title phosphoramidite monomers are suitable for the synthesis of oligonucleotides on solid phase according to conventional amidite chemistry. 4′-Methoxy substitution represents a simple modification of the sugar part of dNs, where beta-D-erythro epimers preferentially adopt N-type (C3′-endo, RNA-like) conformation. Moreover, it imparts superior chemical stability, nuclease resistance, and excellent hybridization properties to modified 4′-methoxyoligodeoxynucleotides. The strong tendency toward RNA-selective hybridization suggests its potential utilization in antisense and/or RNAi technologies.

Druh

C - Kapitola v odborné knize

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název knihy nebo sborníku

Current Protocols in Nucleic Acid Chemistry

ISBN

978-0-471-14270-6

Počet stran výsledku

27

Strana od-do

"1.38.1"-"1.38.27"

Počet stran knihy

98

Název nakladatele

Wiley

Místo vydání

Hoboken

Kód UT WoS kapitoly

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