Synthesis of a branched pentasaccharide sequence of "bisected" structure of N-glycoproteins |
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Authors: | József Kovács István Pintér András Messmer Gábor Tóth |
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Institution: | Central Research Institute for Chemistry, Hungarian Academy of Sciences, H-1525 Budapest Hungary;Institute for General and Analytical Chemistry, Technical University, H-1521 Budapest Hungary |
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Abstract: | For the synthesis of the threefold-branched pentasaccharide, O-alpha-D-mannopyranosyl-(1----3)-O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-(1----4)]-O-alpha-D-mannopyranosyl-(1----6)]-O-beta-D- mannopyranosyl-(1----4)-2-acetamido-2-deoxy-D-glucopyranose (20), which is a part of the structure of the N-glycoproteins, the disaccharide 4-O-(4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-beta-D-mannopyranosyl) -1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-beta-D-glucopyranose was synthesized as a key compound by use of the silver silicate-catalyst procedure. After elimination of the 4-O-acetyl group, a 2-acetamido-2-deoxy-beta-D-glucopyranosyl group was attached according to the phthalimido method. Further elimination of the allyl groups allowed the linkage of two alpha-D-mannopyranosyl groups in the presence of mercury salt. A deblocking sequence consisting of four steps gave 20. |
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Keywords: | Author to whom correspondence should be addressed |
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