790692-16-9Relevant articles and documents
Ring-opening of aziridine-2-carboxamides with carbohydrate C1-O-nucleophiles. Stereoselective preparation of α- and β-O-glycosyl serine conjugates
Ryan, Daniel A.,Gin, David Y.
supporting information; experimental part, p. 15228 - 15229 (2009/03/12)
The stereoselective formation of the α-GalNAc-Ser linkage via the ring opening of aziridine-2-carboxamides with pyranose C1-O-nucleophiles is described. The process is tolerant to the native C2-NHAc group, can be modulated to provide either the α- or β-glycoside through judicious choice of solvent and metal counterion, and is amenable to other classes of O-glycosyl-Ser constructs such as the β-GlcNAc-Ser and α-Man-Ser linkages. This coupling reaction also led to the development of the o-allylbenzyl (ABn) moiety as a new C-terminus carboxyl protective group, which allows for the use of novel methods for N- and C-terminus extension of amino acids following carbohydrate conjugation. Copyright
Conjugation of selenols with aziridine-2-carboxylic acid-containing peptides
Ide, Nathan D.,Galoni?, Danica P.,Van Der Donk, Wilfred A.,Gin, David Y.
, p. 2011 - 2014 (2007/10/03)
The addition of PhSeH to aziridine-2-carboxylic acid containing peptides is described, thus expanding the scope of nucleophiles for the opening of this class of electrophilic peptide substrates. The process offers a new strategy for the generation of usef
