Synthesis of amine- and thiol-modified nucleoside phosphoramidites for site-specific introduction of biophysical probes into RNA

Shengxi Jin, Chandrasekhar V. Miduturu, David C. McKinney, Scott K Silverman

Research output: Contribution to journalArticle

Abstract

For studies of RNA structure, folding, and catalysis, site-specific modifications are typically introduced by solid-phase synthesis of RNA oligonucleotides using nucleoside phosphoramidites. Here, we report the preparation of two complete series of RNA nucleoside phosphoramidites; each has an appropriately protected amine or thiol functional group. The first series includes each of the four common RNA nucleotides, U, C, A, and G, with a 2′-(2-aminoethoxy)-2′-deoxy substitution (i.e., a primary amino group tethered to the 2′-oxygen by a two-carbon linker). The second series encompasses the four common RNA nucleotides, each with the analogous 2′-(2-mercaptoethoxy)-2′-deoxy substitution (i.e., a tethered 2′-thiol). The amines are useful for acylation and reductive amination reactions, and the thiols participate in displacement and oxidative cross-linking reactions, among other likely applications. The new phosphoramidites will be particularly valuable for enabling site-specific introduction of biophysical probes and constraints into RNA.

Original languageEnglish (US)
Pages (from-to)4284-4299
Number of pages16
JournalJournal of Organic Chemistry
Volume70
Issue number11
DOIs
StatePublished - May 27 2005

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Nucleosides
Sulfhydryl Compounds
Amines
RNA
Substitution reactions
Nucleotides
Amination
Acylation
Oligonucleotides
Functional groups
Catalysis
phosphoramidite
Carbon
Oxygen

ASJC Scopus subject areas

  • Organic Chemistry

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Synthesis of amine- and thiol-modified nucleoside phosphoramidites for site-specific introduction of biophysical probes into RNA. / Jin, Shengxi; Miduturu, Chandrasekhar V.; McKinney, David C.; Silverman, Scott K.

In: Journal of Organic Chemistry, Vol. 70, No. 11, 27.05.2005, p. 4284-4299.

Research output: Contribution to journalArticle

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AB - For studies of RNA structure, folding, and catalysis, site-specific modifications are typically introduced by solid-phase synthesis of RNA oligonucleotides using nucleoside phosphoramidites. Here, we report the preparation of two complete series of RNA nucleoside phosphoramidites; each has an appropriately protected amine or thiol functional group. The first series includes each of the four common RNA nucleotides, U, C, A, and G, with a 2′-(2-aminoethoxy)-2′-deoxy substitution (i.e., a primary amino group tethered to the 2′-oxygen by a two-carbon linker). The second series encompasses the four common RNA nucleotides, each with the analogous 2′-(2-mercaptoethoxy)-2′-deoxy substitution (i.e., a tethered 2′-thiol). The amines are useful for acylation and reductive amination reactions, and the thiols participate in displacement and oxidative cross-linking reactions, among other likely applications. The new phosphoramidites will be particularly valuable for enabling site-specific introduction of biophysical probes and constraints into RNA.

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