Protecting Groups for Nucleosides Used in Synthesizing Oligonucleotides

Robert L. Letsinger; Paul S. Miller

doi:10.1021/ja01040a043

Protecting Groups for Nucleosides Used in Synthesizing Oligonucleotides

Robert L. Letsinger, Paul S. Miller

Bloomberg School of Public Health

Research output: Contribution to journal › Article › peer-review

Abstract

Three protecting groups useful in syntheses involving nucleosides are described. These are β-benzoyl propionyl and benzoylformyl for OH groups of nucleosides and isobutyloxycarbonyl for NH₂ of the cytosine ring. The preparation and properties of 3ʹ-O- and 5ʹ-O-(β-benzoylpropionyl)thymidine, 3ʹ-O-benzoylformylthymi-dine, and N⁵-isobutyloxycarbonyl-3ʹ-O-β-benzoylpropionyl)deoxycytidine are described.

Original language	English (US)
Pages (from-to)	3356-3359
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	91
Issue number	12
DOIs	https://doi.org/10.1021/ja01040a043
State	Published - Jun 1969

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Protecting Groups for Nucleosides Used in Synthesizing Oligonucleotides",

abstract = "Three protecting groups useful in syntheses involving nucleosides are described. These are β-benzoyl propionyl and benzoylformyl for OH groups of nucleosides and isobutyloxycarbonyl for NH2 of the cytosine ring. The preparation and properties of 3ʹ-O- and 5ʹ-O-(β-benzoylpropionyl)thymidine, 3ʹ-O-benzoylformylthymi-dine, and N5-isobutyloxycarbonyl-3ʹ-O-β-benzoylpropionyl)deoxycytidine are described.",

author = "Letsinger, {Robert L.} and Miller, {Paul S.}",

year = "1969",

month = jun,

doi = "10.1021/ja01040a043",

language = "English (US)",

volume = "91",

pages = "3356--3359",

journal = "Journal of the American Chemical Society",

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T1 - Protecting Groups for Nucleosides Used in Synthesizing Oligonucleotides

AU - Letsinger, Robert L.

AU - Miller, Paul S.

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N2 - Three protecting groups useful in syntheses involving nucleosides are described. These are β-benzoyl propionyl and benzoylformyl for OH groups of nucleosides and isobutyloxycarbonyl for NH2 of the cytosine ring. The preparation and properties of 3ʹ-O- and 5ʹ-O-(β-benzoylpropionyl)thymidine, 3ʹ-O-benzoylformylthymi-dine, and N5-isobutyloxycarbonyl-3ʹ-O-β-benzoylpropionyl)deoxycytidine are described.

AB - Three protecting groups useful in syntheses involving nucleosides are described. These are β-benzoyl propionyl and benzoylformyl for OH groups of nucleosides and isobutyloxycarbonyl for NH2 of the cytosine ring. The preparation and properties of 3ʹ-O- and 5ʹ-O-(β-benzoylpropionyl)thymidine, 3ʹ-O-benzoylformylthymi-dine, and N5-isobutyloxycarbonyl-3ʹ-O-β-benzoylpropionyl)deoxycytidine are described.

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