Oligonucleotides containing 2′-O-[2-(2,3-dihydroxypropyl)amino-2-oxoethyl]uridine as suitable precursors of 2′-aldehyde oligonucleotides for chemoselective ligation

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• 作者：Eugeny M. Zubin ; Dmitry A. Stetsenko ; Timofei S. Zatsepin ; Michael J. Gait and Tatiana S. Oretskaya
• 关键词：Oligonucleotide ; Conjugate ; Aldehyde ; Oxime ; Hydrazine
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2005
• 出版时间：2005
• 年：2005
• 卷：13
• 期：16
• 页码：4912-4920
• 全文大小：354 K

文摘

2′-O-[2-(2,3-Diacetoxypropyl)amino-2-oxoethyl]uridine 3′-phosphoramidite was prepared and used in solid-phase synthesis to obtain oligonucleotides containing a 1,2-diol group, which may then be converted into a 2′-aldehyde group. The oligonucleotides were conjugated efficiently to various molecules by chemoselective ligation that involves an addition–elimination reaction between the 2′-aldehyde group and a suitable nucleophile, such as a hydrazine, a O-alkylhydroxylamine or an 1,2-aminothiol. The method was applied successfully to the conjugation of peptides to oligonucleotides at the 2′-position.