103166-63-8Relevant academic research and scientific papers
Site-selective conjugation of thiols with aziridine-2-carboxylic acid-containing peptides
Galonic, Danica P.,Van Der Donk, Wilfred A.,Gin, David Y.
, p. 12712 - 12713 (2004)
The synthesis and convergent site-selective conjugation of aziridine-2-carboxylic acid-containing peptides with thiols, both in solution and on solid support, are described. The synthesis and use of FmocAzyOH in this capacity demonstrate both the efficient incorporation and tolerance of the Azy moiety in multistep Fmoc solid-phase peptide synthesis (SPPS), as well as the competence of solution and on-bead ligation through a highly regioselective base-promoted aziridine ring-opening process. Copyright
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
