Simple vesicle fusion allowed the formation of a bilayer lipid membrane from the self‐assembled monolayer of lipoic acid ester 1 (see formula). Film thicknesses determined by surface plasmon resonance (SPR) spectroscopic measurements agree with the theoretical thicknesses of the stretched conformation. Electrochemical impedance spectroscopy (EIS) of the model system shows that the latter exhibits similar electrical properties to biological membranes.

I. Introduction 4495 A. Synthesis of a GlycoundecapeptidesMajor Problems and Solutions 4496 1. Synthesis of the Sialyl−Tn Building Block 4496 2. Solid-Phase Synthesis of Undecaglycopeptide 1 4498 II. O-Glycopeptides Carrying Mono-and Disaccharides 4499 A. O-Glycopeptides Carrying RGalNAc 4499 B. Glycopeptides Carrying the T Antigen (βGal-1,3-RGalNAc) 4500 C. O-Glycopeptides Carrying βGlcNAc 4503 D. O-Fucosylated Glycopeptides 4505 E. O-Glycopeptides Carrying the Sialyl−Tn Antigen (RNeuNAc-2,6-RGalNAc) 4505 F. Collagen Type II Derived Glycopeptides Carrying β-Gal and RGlc-1,2-βGal Side Chains

Based on important cell-biological and biochemical results concerning the structural difference between membrane glycoproteins of normal epithelial cells and epithelial tumour cells, tumour-associated glycopeptide antigens have been chemically synthesised and structurally confirmed. Glycopeptide structures of the tandem repeat sequence of mucin MUC1 of epithelial tumour cells constitute the most promising tumour-associated antigens. In order to generate a sufficient immunogenicity of these endogenous structures, usually tolerated by the immune system, these synthetic glycopeptide antigens were conjugated to immune stimulating components: in fully synthetic two-component vaccines either with T-cell peptide epitopes or with Toll-like receptor2 lipopeptide ligands or in three-component vaccines with both these stimulants. Alternatively, the synthetic glycopeptide antigens were coupled to immune stimulating carrier proteins. In particular, MUC1 glycopeptide conjugates with Tetanus toxoid proved to be efficient vaccines inducing very strong immune responses in mice. The antibodies elicited with the fully synthetic vaccines showed selective recognition of the tumour-associated glycopeptides as was shown by neutralisation and micro-array binding experiments. After booster immunisations, most of the immune responses showed the installation of an immunological memory. Immunisation with fully synthetic three-component vaccines induced immune reactions with therapeutic effects in terms of reduction of the tumour burden in mice or in killing of tumour cells in culture, while MUC1 glycopeptide-Tetanus toxoid vaccines elicited antibodies in mice which recognised tumour cells in human tumour tissues. The results achieved so far are considered to be promising for the development of an active immunisation against tumours.

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A “shot in the arm” for cancer therapy: Coupling of synthetic glycopeptide tandem‐repeat sequences of the epithelial mucin MUC1 with the Thomsen–Friedenreich (T) antigen (A) or a difluoro analogue (B) to tetanus toxoid (TTox) affords synthetic vaccines, which induce very strong immune responses in mice overriding the natural tolerance of the immune system. The induced antibodies are selectively directed against the tumor‐associated MUC1 structures and strongly bind to breast cancer cells of the MCF‐7 cell line.