1019691-75-8Relevant articles and documents
Incorporation of Acid-Labile Masking Groups for the Traceless Synthesis of C-Terminal Peptide α-Ketoacids
Thuaud, Frédéric,Rohrbacher, Florian,Zwicky, André,Bode, Jeffrey W.
, p. 3670 - 3673 (2016)
An optimized protocol for the masking of α-ketoacids with acid-labile cyclic acetal protecting groups is reported. Unlike prior approaches, these new conditions allow the synthesis of protected α-ketoacids bearing aromatic, hindered alkyl, and protected polar side chains. Attachment to a Wang-type linker and solid support provides a resin that delivers fully unprotected C-terminal peptide α-ketoacids upon resin cleavage. These peptides are the key starting materials for chemical protein synthesis using the α-ketoacid-hydroxylamine ligation.
Stereoretentive synthesis and chemoselective amide-forming ligations of C-terminal peptide α-ketoacids
Ju, Lei,Lippert, Alexander R.,Bode, Jeffrey W.
, p. 4253 - 4255 (2008/12/20)
C-Terminal peptide cyanosulfur ylides are readily converted to C-terminal peptide α-ketoacids, poised for chemoselective amide-forming reactions with hydroxylamines. These easily prepared and bench stable ylides are quickly and selectively oxidized with a