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Total Synthesis of Sialylated and Sulfated Oligosaccharide Chains from Respiratory Mucins
Author(s) -
Xia Jie,
Alderfer James L.,
Piskorz Conrad F.,
Matta Khushi L.
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20000915)6:18<3442::aid-chem3442>3.0.co;2-v
Subject(s) - trisaccharide , chemistry , disaccharide , oligosaccharide , tetrasaccharide , stereoselectivity , stereochemistry , acceptor , mucin , total synthesis , biochemistry , catalysis , polysaccharide , physics , condensed matter physics
The total syntheses of several complex oligosaccharide moieties that occur in the core structure of sulfated mucins are reported. A trisaccharide acceptor was obtained through regio‐ and stereoselective sialylation of methyl (6‐ O ‐pivaloyl‐ β ‐ D ‐galactopyanosyl)‐(1→3)‐4, 6‐ O ‐benzylidene‐2‐acetamido‐2‐deoxy‐ α ‐ D ‐galactopyranoside with a novel sialyl donor. A tetrasaccharide, pentasaccharide, and hexasaccharide were constructed in predictable and controlled manner with high regio‐ and stereoselectivity after the successful preparation and employment of a disaccharide donor, trisaccharide donor, disaccharide acceptor, and trisaccharide acceptor building blocks. Finally, a mild oxidative cleaving method was adopted for the selective removal of 2‐naphthylmethyl (NAP) in the presence of benzyl groups.