Antigen Globo

Scheme 10.3 Preparation of the tumor-associated antigen globo-H by a two-direction...

Scheme 59. Automated synthesis2 of tumor-associated antigen Globo-H hexasaccharide 304.

T. Zhu and G.-J. Boons, A two-directional and highly convergent approach for the synthesis of the tumor-associated antigen Globo-H, Angew. Chem., Int. Ed. Engl., 38 (1999) 3495-3497. 

Z. Wang, L. Zhou, K. Ei-Boubbou, X. S. Ye, and X. Huang, Multi-component one-pot synthesis of the tumor-associated carbohydrate antigen Globo-H based on preactivation of thioglycosyl donors,... 

Fully protected tumor-associated carbohydrate antigen Globo-H (50), a potential breast and prostate cancer vaccine [54, 55], was assembled by automated solid support synthesis using oct-4-ene-l,8-diol linker 49 and building blocks 51-56 (Scheme 20.15). The linker is stable to acid and base but is cleaved cleanly by olefin metathesis [56]. The octenediol linker performs best on Merrifield s PS resin, affording routinely loadings in a range of 0.1-0.3 mmol g 1. 

KLH usually is more immunogenic than BSA. It was used, for example, in the synthesis of a complex vaccine 58 containing five tumour-associated carbohydrate antigens (globo H, GM2, Sialyl-Tn, T and Tn) linked to unnatural amino acids (Scheme 17). ... 

SOLID-PHASE SYNTHESIS OF THE HEXASACCHARIDE GLOBO-H ANTIGEN PROGRESS AND LIMITATIONS... 

Scheme 2.18 Solid-phase synthesis of the globo-H trisaccharide antigen.

Some gangliosides of the globo series (Globo-H, sLcx hexasaccharyl ceramide, etc.) are useful cancer cell markers because they are elevated in the membranes of certain types of tumor cells such as melanomas and metastatic brain tumors. A number of GSLs play a role as tumor-associated carbohydrate antigens (TACAs)... 

Beside the ABO blood group system a number of additional carbohydrate-based antigenic determinants are known (O Table 2), which are, however, not only recognized by antibodies. Some of them are more highly expressed on tumor cells and therefore can be described as tumor-associated antigens [115]. Synthetic tumor-associated antigens such as Lewis y or Globo H have been used in the development of antitumor vaccines [116,117]. 

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