312933-66-7Relevant academic research and scientific papers
Enzyme-labile protecting groups in peptide synthesis: Development of glucose- and galactose-derived urethanes
Gum, Andrew G.,Kappes-Roth, Thomas,Waldmann, Herbert
, p. 3714 - 3721 (2007/10/03)
The development of the tetra-O-acetyl-D-glucopyranosyloxycarbonyl (AGlOC) and tetra-O-acetyl-β-D-galactopyranosyloxycarbonyl (AGalOC) protecting groups, which are fully enzyme-labile, carbohydrate-derived urethanes, is described. The protected amino acids were easily synthesized and subsequently converted into a series of model dipeptides through classical peptide couplings. Cleavage of an α/β-anomeric mixture of a model AGlOC dipeptide was achieved with a 'one-pot' procedure in good yield. To gain a better understanding of the enzymatic deprotection reaction, the AGalOC group was removed formation (lipase catalyzed deacetylation, followed by β-galactosidase catalyzed glycosidic bond fragmentation). Under these very mild reaction conditions (aq. buffer pH7.0, 37°C), the desired N-terminal, unprotected dipeptide conjugates were obtained. The methodology was further utilized for the synthesis of an advanced tetrapeptide model system.
