Maleimide-Dimethylfuran exo Adducts: Effective Maleimide Protection in the Synthesis of Oligonucleotide Conjugates

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• 作者：Albert Sa虂nchez ; Enrique Pedroso ; Anna Grandas
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：August 19, 2011
• 年：2011
• 卷：13
• 期：16
• 页码：4364-4367
• 全文大小：754K
• 年卷期：v.13,no.16(August 19, 2011)
• ISSN：1523-7052

文摘

The reaction of maleimide-containing compounds with 2,5-dimethylfuran gives a mixture of exo and endo isomers from which the exo cycloadduct can be easily isolated taking advantage of its stability in concentrated aqueous ammonia. Bifunctional compounds incorporating a dimethylfuran-protected maleimide (exo adduct) have been attached to resin-linked oligonucleotide chains. Removal of protecting groups masking oligonucleotide functionalities followed by retro-Diels鈥揂lder maleimide deprotection affords maleimido-oligonucleotides suitable for conjugation, as assessed by their reaction with different thiols.