Peptidic oligosaccharide mimetics

Figure 2. The solid phase chemistry developed for the construction of an oligosaccharide mimetic library is shown. Glucosaminouronic acid building blocks A are linked using standard peptide coupling chemistry producing the homotetramer B.

One of the earliest reported carbohydrate-mimetic peptides was the dodecapeptide DVFYPYPYASGS [10]. The peptide acts as a ligand for con-canavalin A, a lectin which binds oligosaccharides bearing terminal a-linked... 

More recently, multivalent approaches [328,329,330] were reported. Based on molecular modeling approaches, non-sugar sLe mimetics [331,332,333] such as 107 (IC5o = 86, 6.1, and 30 jM for E-, P- and L-selectins respectively) [331] were created. A peptide mimicking the sialyl Lewis oligosaccharide has been identified [334], this concept is discussed in more detail the next chapter. 

Carbohydrate-mimetic peptides, peptides capable of acting as molecular mimetics of carbohydrates. The first carbohydrate-mimetic peptides that bound to the lectin concanavalin A acting as mimics of mannose-containing oligosaccharides were identified in 1992. One year later, the first peptide to mimic a carbohydrate... 

Examples of studies on specific peptides and proteins in membranes are an SS NMR investigation of the selective disruption of lipid membranes by p-hairpin antimicrobial peptide protegrin-1 in multinuclear mixed lipid layer PG and PC +/ cholesterol MAS/NMR studies of apolipoprotein A1 mimetic peptides in PC membranes with cholesterol with a comparison of the interactions of two 18-mers with the same composition but different sequence with the membrane the peptide sequence GSSSGRGDSPA having a hydrophobic extender to the N-terminus was studied with dextran oligosaccharides and hexyl ligands boimd onto a polyvinylamine backbone to mimic interactions at the ECM. ... 

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