Synthesis of Azidoaniline Derivatives of Oligonucleotides and Investigation of Their Photochemical Behavior

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• 作者：Tatyana S. Godovikova ; Vera D. Knorre ; Galiya A. Maksakova ; and Vladimir N. Sil'nikov
• 刊名：Bioconjugate Chemistry
• 出版年：1996
• 出版时间：May 1996
• 年：1996
• 卷：7
• 期：3
• 页码：343 - 348
• 全文大小：271K
• 年卷期：v.7,no.3(May 1996)
• ISSN：1520-4812

文摘

A series of aryl azides,p-N₃C₆H₄NH(CH₂)_nNH₂with n = 2-6, have been synthesized and usedtoprepare oligonucleotide derivatives carrying photoreactive thep-azidoaniline residue. Reactive moietieshave been coupled to the 5'-terminal phosphate of d(pGATACCAA)[compounds IV(b), IV(c),andIV(e) with n = 3, 4, and 6, respectively]and of d(pGCC) [compound V(b) with n =3] via aphosphoamide bond. Irradiation at wavelengths over >300 nm ofIV(b) and V(b) (n = 3)resulted incleavage of the P-N bond. However, under the same reactionconditions, the P-N bond remainedintact for compounds containing longer spacers [IV(c)and IV(e)]. Intraduplex reaction of thelatterderivatives withd(GGTATCp)NH(CH₂)₆NH₂resulted in cross-linking dependent on the presence ofan aliphatic amino group. The results obtained have demonstratedthat the azidoaniline derivativesof oligonucleotides capable of the affinity modification of a specifictarget can be prepared. However,the sufficiently long aliphatic spacer group is necessary to preventP-N bond cleavage within thephotoreactive oligonucleotide.