Glycopeptides mimics

Figure 14.7 Models of phosphorylated high-mannose M7 and a glycopeptide mimic obtained by MD calculation showing similar conformations. They are seen from the point of interaction with the mannose-6-phosphate receptor. Disaccharide phosphates are emphasized as spheres.76...

We have developed two methods for the synthesis of natural and unnatural products from D-glucose. Enantio-and diastereo-switching method established a new strategy for the synthesis of four possible stereomers for natural products synthesis, and this powerful method was successfully applied to the synthesis of unnatural protein phosphatase inhibitors. The second synthetic method involved the preparation of the urea-glycosidic linkages for the synthesis of glycopeptide mimics. 

Synthetic Studies of Glycopeptide Mimics with Urea-glycosyl Bonds... 

Retrosynthetic analysis for the synthesis of a key building blockl for such a glycopeptide mimics is shown in Figure 10. It was envisaged that the synthesis of I could be achieved by a coupling reaction of the glycosyl isocyanates II and the amino acid derivatives III, and initial work focused on the synthesis of the glycosyl isocyanates IV. 

Figure 10. Retrosynthetic analysis for the glycopeptide mimics with urea-giycosyi bonds...

Figure 13. Synthesis of glycopeptide mimics with a urea-glycosyl...

Macmillan D, Daines AM, Bayrhuber M, Fitsch SL, Solid-phase synthesis of thioether-linked glycopeptide mimics for application to glycoprotein semisynthesis, Org. Lett., 4(9) 1467-70, 2002. 

Scheme 20 C-Glycopeptide mimic of a MUCl antigen linked to TTox.

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