Peptide-carbohydrate mimicry

Structural and Functional Studies of Peptide-Carbohydrate Mimicry... 

Peptide-Carbohydrate Mimicry in Enzyme Active Sites. 93... 

Keywords Molecular modeling NMR spectroscopy Peptide-carbohydrate mimicry Protein-ligand interactions X-ray crystallography... 

In contrast, the existence of peptide-carbohydrate mimicry is more surprising in that it is difficult to picture how these two different classes of compounds could mimic each other. The origin of this effect at the molecular level has been the subject of recent investigations by NMR spectroscopy, X-ray crystallography, and molecular modeling. In combination with functional data, these studies provide insight into the nature of this phenomenon. 

While functional (immunological) mimicry has been established, the basis of mimicry on the molecular level remains to be explained. Several hypotheses have been put forward one of the earliest was that the side chains of aromatic amino acid residues might mimic the hydrophobic faces of the pyranosyl rings of carbohydrates. Before 1997, no structural evidence was available to support or discount these hypotheses. The nature of peptide-carbohydrate mimicry on the molecular level became the subject of structural investigations, and the resulting studies along with functional data will be discussed below. 

Overall, these chitinase inhibitors provide an interesting example of peptide-carbohydrate mimicry. As described above for several other systems, mimicry consists of a mixture of structurally mimetic interactions and other favorable interactions with the receptor. Of the structurally mimetic interactions, the mimicry by argifin of the N-acetyl group, and part of the pyranosyl... 

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