Synthese der T-antigenen trisaccharide O-β-d-galactopyranosyl-(1→3)-O-(2-acetamido-2-desoxy-α-d-galactopyranosyl)-(1→6)-d-galactopyranose und O-β-d-galactopyranosyl-(1→3)-O-(2-acetamido-2-desoxy-α-d-galactopyranosyl)-(1→6)-d-glucopyranose und deren anknüpfung an proteine |
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Authors: | Hans Paulsen Michael Paal |
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Institution: | Institut für Organische Chemie und Biochemie der Universität Hamburg, D-2000 Hamburg 13 Bundesrepublik Deutschland |
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Abstract: | The synthesis of the trisaccharides O-β-d-galactopyranosyl-(1→3)-O-(2-acetamido-2-deoxy-α-d-galactopyranosyl)-(1→6)-d-galactopyranose (15) and O-β-d-galactopyranosyl-(1→3)-O-(2-acetamido-2-deoxy-α-d-galactopyranosyl)-(1→6)-d-glucopyranose (27) is described and the synthesis of α-d-glycosides by reaction of 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-d-galactopyranosyl chloride with highly reactive hydroxyl groups is discussed. The trisaccharide 27 was coupled with serum albumin by formation of an imine intermediate and reduced to an amine, to yield a synthetic T-antigen. A similar coupling of 15 was unsuccessful. |
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