earticle

영어

With the completion of the human genome projects, one of the most important scientific issues is to investigate the biological function of each protein. In higher organisms, the functional outputs of the numerous gene products seem to be much more complex when compared to the number of genes, emphasizing the importance of post-translational modifications such as glycosylation and phosphorylation. Despite the fact that glycoproteins are involved in various biological phenomena, the systematic studies of the effects of protein glycosylation have been limited due to the heterogeneity and structural complexity of carbohydrates. In order to access glycopeptides and glycoproteins of defined structure, various chemical, enzymatic and genetic approaches have been developed. As glycopeptide mimetics, we envisioned to develop glycopeptoids because peptoids have many advantages over peptides, including easy synthesis of libraries, a myriad of chemical diversity, proteolytic resistance and improved cell permeability. For the synthesis of glycopeptoids, we have employed the well established ‘submonomer strategy’ on the solid-phase using many commercially available primary amines and synthetically prepared sugar amines. In addition, diastereomeric sugar monomers were differentiated by using different amine linkers, resulting in successful sequencing by tandem mass spectrometry (MS/MS). Glycopeptoids should be useful chemical tools for various biological applications including studies for binding affinity to specific proteins or lectins, development of therapeutics such as antibiotics, and profiling studies of diseases.