A second generation synthesis of the MBr1 (Globo-H) breast tumor antigen: New application of the n-pentenyl glycoside method for achieving complex carbohydrate protein linkages

A new synthesis of the hexasaccharide MBr1 antigen (globo-H) is reported. A revised construction with improved efficiency was necessary because an ant i-cancer vaccine containing this antigen is entering phase II and phase III clinical trials for prostate cancer. The key feature of this second genera tion synthesis is the preparation of globo-H as its n-pentenyl glycoside. T his group serves as an anomeric protecting group and as a linker for biocon jugation to carrier protein. The resultant synthesis allows for the product ion of suitable quantities of globo-H for clinical trials.