Chapter 4 Chemical Synthesis of Glycopeptides

Abstract

Publisher Summary This chapter discusses the chemical synthesis of glycopeptides. Glycoproteins are composed of a polypeptide backbone which is glycosylated with one or more carbohydrate chains. The availability of glycopeptides from natural sources is limited because of the low concentration and the microheterogeneity of biological glycoconjugates. The advances in carbohydrate and peptide chemistry in the last decade have created generally applicable methodologies for the synthesis of glycopeptides as model compounds for biochemical and structural investigations. Thus, glycopeptides can be made available with variations in the peptide and the carbohydrate part in superior purity and quantity. The synthesis of glycopeptides requires a combination of synthetic methods from both carbohydrate and peptide chemistry. The glycosylamino acids can be used for incorporation into a peptide chain by application of standard peptide chemistry methods. In case of a solution phase glycopeptide synthesis, the construction of the peptide chain may start on either the C- or N-terminal side of the glycosylamino acid.