133010-18-1Relevant articles and documents
Metal-free approach for hindered amide-bond formation with hypervalent iodine(iii) reagents: application to hindered peptide synthesis
Lee, Hyo-Jun,Huang, Xiao,Sakaki, Shigeyoshi,Maruoka, Keiji
supporting information, p. 848 - 855 (2021/02/09)
A new bio-inspired approach is reported for amide and peptide synthesis using α-amino esters that possess a potential activating group (PAG) at the ester residue. To activate the ester functionality under mild metal-free conditions, we exploited the facile dearomatization of phenols with hypervalent iodine(iii) reagents. Using a pyridine-hydrogen fluoride complex, highly reactive acyl fluoride intermediates can be successfully generated, thereby allowing for the smooth formation of sterically hindered amides and peptides from bulky amines and α-amino esters, respectively.
Duality of mechanism in the tetramethylfluoroformamidinium hexafiuorophosphate-mediated synthesis of N-benzyloxycarbonylamino acid fluorides
Fiammengo,Licini,Nicotra,Modena,Pasquato,Scrimin,Broxterman,Kaptein
, p. 5905 - 5910 (2007/10/03)
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Amino acid fluorides: Their preparation and use in peptide synthesis
Bertho, Jean-Noeel,Loffet, Albert,Pinel, Catherine,Reuther, Florence,Sennyey, Gerard
, p. 1303 - 1306 (2007/10/02)
Z or Fmoc amino acid fluorides have been prepared from the protected amino acids and cyanuric fluoride, and have been tested both in the condensation with simple amino acid esters and in Solid Phase Peptide Synthesis.