Maleimide-Dimethylfuran exoAdducts: Effective Maleimide Protection in the Synthesis of Oligonucleotide Conjugates.
- Resource Type
- Article
- Authors
- Albert SaÌnchez; Enrique Pedroso; Anna Grandas
- Source
- Organic Letters. Aug2011, Vol. 13 Issue 16, p4364-4367. 4p.
- Subject
- *ORGANIC synthesis
*IMIDES
*FURANS
*OLIGONUCLEOTIDES
*CONJUGATED polymers
*AMMONIA
*FUNCTIONAL groups
*CHEMICAL reactions
- Language
- ISSN
- 1523-7060
The reaction of maleimide-containing compounds with 2,5-dimethylfuran gives a mixture of exoand endoisomers from which the exocycloadduct can be easily isolated taking advantage of its stability in concentrated aqueous ammonia. Bifunctional compounds incorporating a dimethylfuran-protected maleimide (exoadduct) have been attached to resin-linked oligonucleotide chains. Removal of protecting groups masking oligonucleotide functionalities followed by retro-DielsâAlder maleimide deprotection affords maleimido-oligonucleotides suitable for conjugation, as assessed by their reaction with different thiols. [ABSTRACT FROM AUTHOR]