Synthesis of 4′-methoxy 2′-deoxynucleoside phosphoramidites for incorporation into oligonucleotides
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Synthesis of 4′-methoxy 2′-deoxynucleoside phosphoramidites for incorporation into oligonucleotides
Original language description
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.
Czech name
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Czech description
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Classification
Type
C - Chapter in a specialist book
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Book/collection name
Current Protocols in Nucleic Acid Chemistry
ISBN
978-0-471-14270-6
Number of pages of the result
27
Pages from-to
"1.38.1"-"1.38.27"
Number of pages of the book
98
Publisher name
Wiley
Place of publication
Hoboken
UT code for WoS chapter
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