Diels--Alder bioconjugation of diene-modified oligonucleotides.

Hill, K W; Taunton-Rigby, J; Carter, J D; Kropp, E; Vagle, K; Pieken, W; McGee, D P; Husar, G M; Leuck, M; Anziano, D J; Sebesta, D P

Hill, K W; Taunton-Rigby, J; Carter, J D; Kropp, E; Vagle, K; Pieken, W; McGee, D P; Husar, G M; Leuck, M; Anziano, D J; Sebesta, D P.

Afiliación

Hill KW; NeXstar Pharmaceuticals, 2860 Wilderness Place, Boulder, Colorado 80301, USA. dsebesta@proligo.com

J Org Chem ; 66(16): 5352-8, 2001 Aug 10.

Article en En | MEDLINE | ID: mdl-11485455

RESUMEN

In an effort to offer complementary technology for covalent biomolecule modification (bioconjugation), we have developed a method that exploits the aqueous acceleration of Diels--Alder reactions for this purpose. Three different diene phosphoramidite reagents have been synthesized that enable diene modification of synthetic oligonucleotides prepared by the phosphoramidite method. Clean and efficient Diels--Alder cycloaddition of these diene oligonucleotides with maleimide dieneophiles was carried out, and the labeled oligonucleotide bioconjugates were characterized by HPLC and electrospray mass spectrometry. Dieneophile stoichiometry, temperature, and pH are all parameters that were shown to influence the efficiency of the process.

Asunto(s)

Oligonucleótidos/síntesis química; Biotinilación; Cumarinas/química; Fluoresceína/química; Oligonucleótidos/química; Temperatura

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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Oligonucleótidos Idioma: En Revista: J Org Chem Año: 2001 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos

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