92963-03-6Relevant academic research and scientific papers
Exploration of an imide capture/N,N-acyl shift sequence for asparagine native peptide bond formation
Mhidia, Reda,Boll, Emmanuelle,Fécourt, Fabien,Ermolenko, Mikhail,Ollivier, Nathalie,Sasaki, Kaname,Crich, David,Delpech, Bernard,Melnyk, Oleg
supporting information, p. 3479 - 3485 (2013/07/05)
Imide capture of a C-terminal peptidylazide with a side-chain thioacid derivative of an N-terminally protected aspartyl peptide leads to the formation of an imide bond bringing the two peptide ends into close proximity. Unmasking of the Nα protecting group and intramolecular acyl migration results in the formation of a native peptide bond to asparagine.
Synthesis of imides, N-acyl vinylogous carbamates and ureas, and nitriles by oxidation of amides and amines with dess-martin periodinane
Nicolaou,Mathison, Casey J. N.
, p. 5992 - 5997 (2007/10/03)
Expanding our synthetic tool repertoire: The DMP-mediated oxidation of a range of amide substrates has been demonstrated, affording the corresponding imides and N-acyl vinylogous carbamates and ureas. Likewise, an array of benzylic and related amines have also been successfully converted into their nitrile counterparts (see scheme; DMP = Dess-Martin periodinane). (Chemical Equation Presented)
