Glycosylations solid-phase synthesis

Urge, L., Otvos Jr., L., Lang, E., Wroblewski, K., Laczko, I., and Hollosi, M. (1992) Fmoc-protected, glycosylated asparagines potentially useful as reagents in the solid-phase synthesis of N-glycopeptides. Carbohydr. Res. 235, 83-93. 

The solid-phase synthesis of glycopeptides was first realized by applying the polymeric benzyl ester principle of Merrifield. According to this methodology, Lavielle and associates (50) used 7V-(tm-butyloxycarbonyl)-<9-glycosyl serine derivative 153 for condensation with resin-linked alanine 154. 

A major contribution to the use of glycosyl trichloroacetimidates in the solid-phase synthesis of oligosaccharides came from the group of T. Ogawa (Scheme 4.7).5... 

Scheme 5.10 Application of NPGs in solid-phase synthesis (a) immobilization of the glycosyl donor (b) immobilization of the glycosyl acceptor.66...

Scheme 14.1 Strategies for glycopeptide library synthesis Strategy 1 chemical or enzymatic glycosylation of peptide or glycopeptide Strategy 2 the building-block approach. While enzymes have not yet been used in the solid-phase synthesis of glycopeptide libraries, several resin-bound glycopeptides have been glycosylated enzymatically.36,114...

The tetra-O-benzylated A-Fmoc derivative of 165 was then incorporated by solid-phase synthesis into a helix-forming glycoheptadecapeptide, Ac-Tyr-Lys-Ala-Ala-Ala-Ala-Lys-Ala-Ala-Cgaa((3-D-Gal-C-)-Ala-Lys-Ala-Ala-Ala-Ala-Lys-NH2 (Cgaa= C-glycosylated amino acid)J128l... 

O. Seitz and H. Kunz, A novel allylic anchor for solid-phase synthesis. Synthesis of protected and unprotected O-glycosylated mucin-typc glycopeptides, Angew. Chem. lnt. Ed. Engl. 34 803 (1995). 

J. Rademann and R. R. Schmidt, Solid-phase synthesis of a glycosylated hexapeptide of human sialophorin, using the trichloroacetimidate method, Carbohydr. Res. 269 217 (1995). 

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