Cathy Miller

Improving Glycopeptide Synthesis:  A Convenient Protocol for the Preparation of β-Glycosylamines and the Synthesis of Glycopeptides

Discussion created by Cathy Miller on May 31, 2019

Glycopeptide Synthesis

 

Herein we apply a recently introduced protocol using ammonium carbamate in methanol to the amination of crude chitobiose leading to 1,β-aminochitobiose. This simple, one-step procedure allows a facile preparation of unstable glycosylamines in contrast to the commonly implemented ammonium bicarbonate based amination of water-soluble carbohydrates. The new amination protocol leads to an improved synthesis of the key chitobiosyl-asparagine building block for the SPPS of glycopeptides. The utility of the method is demonstrated with the synthesis of a 39-amino acid glycoprotein.

Outcomes