A conformationally preorganized universal solid support for efficient oligonucleotide synthesis.

A conformationally preorganized universal solid support for efficient oligonucleotide synthesis. Research Abstract Details 

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A conformationally preorganized universal solid support for efficient oligonucleotide synthesis. Abstract Text:

Andrei P Guzaev,Muthiah Manoharan,

A novel, conformationally preorganized nonnucleosidic universal solid support for oligonucleotide synthesis was developed. The solid support featured two chemically equivalent hydroxy groups locked in syn-periplanar orientation and orthogonally protected with 4,4'-dimethoxytrityl and acetyl groups. The solid support was extensively tested in the preparation of oligonucleotides and their phosphorothioate analogues containing 2'-deoxy, 2'-O-methyl, and 2'-O-methoxyethylnucleoside residues at the 3'-terminus. Upon completion of oligonucleotide chain assembly, the support-bound oligonucleotide material was treated with concentrated ammonium hydroxide, which removed the O-acetyl protection. The deprotected hydroxy group then effected the transesterification of a phosphate linkage between the solid support and the 3'-terminal nucleoside residue to result in a facile release of the oligonucleotide to solution. The kinetics of the release process was studied in a continuous flow of concentrated aqueous ammonium hydroxide at a temperature of 300.15 K. Optimal conditions for the release of oligonucleotides depending on the chemistry of the backbone and 3'-terminal nucleoside residue were formulated.

A conformationally preorganized universal solid support for efficient oligonucleotide synthesis. Publishing Authors By Initials

AP Guzaev,M Manoharan,

For similar biochemical phenomena, metabolism, and nutrition: biochemical phenomena: structure-activity relationship research abstracts see: biochemical phenomena, metabolism, and nutrition: biochemical phenomena: structure-activity relationship research

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A conformationally preorganized universal solid support for efficient oligonucleotide synthesis. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Journal of the American Chemical Society

VOLUME: 125

Page Numbers: 2380-1

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 5

MONTH: Mar

YEAR: 2003

A conformationally preorganized universal solid support for efficient oligonucleotide synthesis. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

A conformationally preorganized universal solid support for efficient oligonucleotide synthesis. Keywords Mesh Terms:

KEYWORDS: Structure-Activity Relationship

MESH TERMS: chemistry

Chemical & Substance for Abstract: A conformationally preorganized universal solid support for efficient oligonucleotide synthesis. Information

Substance Name: ammonium hydroxide

Registry Number: 1336-21-6

Grant and Affiliation Information for A conformationally preorganized universal solid support for efficient oligonucleotide synthesis.

AFFILIATION: Department of Medicinal Chemistry, Isis Pharmaceuticals, 2292 Faraday Avenue, Carlsbad, CA 92008, USA. aguzaev@isisph.com

Country: United States

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MEDLINETA: J Am Chem Soc

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