Chemistry and biochemistry of D- and L-fucose.

Publisher Summary This chapter discusses the various aspects of the chemistry of fucoses, especially the developments made in this field, and explains their metabolism and biochemistry while pointing out the possible biological functions and medical applications of fucoses and their compounds. Fucose is a 6-deoxyhexose having the “galacto” configuration—that is, it has cis-hydroxyl groups on C-3 and C-4. D-Fucose is usually found in plants and some microorganisms, in relatively simple glycosides comprising only a few sugar units. Some plant glycosides and polysaccharides crossreact with reagents for blood-group antigens, and interesting crossreactions has also been shown by methylated-fucose haptens and L-fucose-specific lectins. Great interest has been shown in the characterization of glycosyltransferases in connection with the studies on the tissue localization and mechanism of the biosynthesis of other animal glycoproteins. L-Fucose is found to inhibit the growth of some cells in culture, but only at high doses, and to inhibit the growth of implanted, mammary tumors in rats. The conversion of GDP-D-Man into GDP-Fuc serves as a preliminary stage in the biosynthesis of L-fucans, and its hydrolysis affords free L-fucose.

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