7423-55-4Relevant articles and documents
Maleimide-dimethylfuran exo adducts: Effective maleimide protection in the synthesis of oligonucleotide conjugates
Sanchez, Albert,Pedroso, Enrique,Grandas, Anna
supporting information; experimental part, p. 4364 - 4367 (2011/10/18)
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-Alder maleimide deprotection affords maleimido-oligonucleotides suitable for conjugation, as assessed by their reaction with different thiols.
Recognition-mediated facilitation of a disfavored Diels - Alder reaction
Bennes, Raphael,Philp, Douglas,Spencer, Neil,Kariuki, Benson M.,Harris, Kenneth D. M.
, p. 1087 - 1090 (2008/02/09)
(matrix presented) The rational design of a system which is capable of accelerating and facilitating a thermodynamically disfavored Diels-Alder cycloaddition between a furan and a maleimide is presented. The origins of the acceleration and facilitation of the cycloaddition reaction are traced by kinetic studies-allied to results from 1H NMR spectroscopy and X-ray crystallography-to the formation of strong intramolecular hydrogen bonds in the cycloadduct.