Design and Synthesis of Peptide Mimetics of GDP-Fucose: Targeting Inhibitors of Fucosyltransferases

• DOI: 10.1055/s-2003-44984
• Publication Date: 2004-01-21T03:09:44Z
• Authors: Tetsuya Kajimoto; Toru Tanaka; Chihiro Tsuda; Tsuyoshi Miura; Toshiyuki Inazu; Shuichi Tsuji; Shoko Nishihara; Mitsuko Hisamatsu
• Keywords: 0303 health sciences; 03 medical and health sciences

Novel peptide mimetics of GDP-fucose were designed and synthesized targeting inhibitors of the fucosyltransferases that transfer L-fucose from GDP-fucose to oligosaccharides, on the basis of the background that nikkomycinZ, a peptide mimetic of UDP-N-acetylglucosamine, shows potent inhibitory activity toward an N-acetylglucosamine transfer enzyme. The synthetic routes of the GDP-fucose mimetics take advantage of an enzymatic aldol reaction catalyzed by L-threonine aldolase to prepare the guanine carrying β-hydroxy-α-L-amino acid, a key synthetic intermediate.