Journal of the American Chemical Society 2001-01-10

Total syntheses of tumor-related antigens N3: probing the feasibility limits of the glycal assembly method.

H M Kim, I J Kim, S J Danishefsky

Index: J. Am. Chem. Soc. 123(1) , 35-48, (2001)

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Abstract

The total syntheses of two octasaccharide antigens isolated from human milk, 1 and 2, and their corresponding allyl glycosides, 3 and 4, have been achieved by utilizing the glycal method. Convergent assembly of the core hexasaccharides and concurrent introduction of two alpha-L-fucosyl moieties at the late stage of the syntheses provided these complex carbohydrates in a concise manner. With synthetic material obtained, biological evaluations of these antigens as potential gastrointestinal cancer immunotherapeutic agents have been initiated.