Chemical synthesis of GDP-fucose analogs and their utilization by the Lewis *A(1 → 4) fucosyltransferase
- 1 July 1990
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 68 (7) , 1063-1071
- https://doi.org/10.1139/v90-165
Abstract
Chemical syntheses are reported for GDP-fucose (5), GDP-3-deoxy-fucose (6), and GDP-arabinose (7), the demethyl analog of 5. All three sugar nucleotides were found to act as donor substrates for an α(1 → 4) fucosyltransferase isolated from human milk when *BDGal(1 → 3)*BDGlcNAc-O(CH2)8COOMe (1) was used as the acceptor. The rate of transfer of sugar residues to 1 was measured using a coupled spectrophotometric assay and was found to be 100% (5), 2.3% (6), and 5.9% (7). The product Lea-active oligosaccharide analogs were identified by both an enzyme-linked immunosorbent assay (ELISA) and by 1H NMR spectroscopy. Keywords: glycosyltransferase, oligosaccharide synthesis, sugar-nucleotide analog, ELISA assay, fucosyltransferase.Keywords
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