L-Fucose: occurrence, physiological role, chemical, enzymatic and microbial synthesis

Abstract

An easy source of unusual monosaccharides such as the 6-deoxyhexose, L-fucose are certain microbial extracellular polysaccharides (EPS), best known for their thickening, gelling or emulsifying properties. L-Fucose and L-fucose containing oligosaccharides have potential application in the medical ®eld in preventing tumour cell colonisation of the lung (anticancer effect), in controlling the formation of white blood cells (anti-in¯ammatory effect), in the treatment of rheumatoid arthritis, in the synthesis of antigens for antibody production (rational immunisation) and in cosmeceuticals as skin moisturing agent. L-Fucose production via chemical synthesis is laborious and suffers from low yield, while direct extraction from brown algae is costly and subject to seasonal variations in supply volume and quality. Enzymatic synthesis is currently under investigation. Chemical or enzymatic hydrolysis of L-fucose-rich microbial EPS opens up a new route towards ef®cient L-fucose production. This review deals with the properties, occurrence, physiological roles, chemical, enzymatic and microbial production of L-fucose.

Structure and Substrate Specificity of a Eukaryotic Fucosidase from Fusarium graminearum

“…values of 2.9, 2.9, and 3.5 Å of 299, 305, and 304 residues aligned, respectively (PDB codes 3MO4, 3EYP, and 3GZA) (19,61). 3 Both the overall folds of the N-terminal domains and active site residues are well conserved between FgFCO1 and bacterial homologues (Fig. 4, a and c).…”

“…In mammals L-Fuccontaining conjugates in the form of glycans, glycoproteins, or glycolipids in particular are involved in forming structural determinants of ABO blood group antigens, mediating hostmicrobe interactions, leukocyte-endothelial adhesion, fertilization and embryonic development, and signal transduction via O-fucosylation directly on Ser and Thr of specific types of protein modules as well as implicated in various human disease states including cancer, inflammation, and fucosidosis (1)(2)(3)(4).…”

“…The requirement for fucosylation on xyloglucan in growth and development does not seem to be absolute, as Arabidopsis mur2 mutants lacking fucosyltransferase appear to grow normally despite having no fucosylation in its xyloglucan (13). Besides the aforementioned biological distribution and functions of fucose, L-Fuc is also present inbrown algal polysaccharide fucoidan as the main-chain and side-chain residues with substantial amounts of sulfation and acetylation modifications (14), bacterial and fungal exopolysaccharides (3,4), bacterial lipopolysaccharides (3,4), and nonmammalian animals (3,4).…”

Characterization of a Planctomycetal Organelle: a Novel Bacterial Microcompartment for the Aerobic Degradation of Plant Saccharides

“…Optimal L-fucose and L-rhamnose metabolism could be very important for planctomycete niche specialization. These sugars are commonly found in the extrapolysaccharides of bacteria and fungi (72), lipids (73), and plant and animal saccharides (53,74,75). Planctomycetes have been shown to attach to detritus (marine snow), which is composed of decaying plant and animal materials that most likely contain L-fucose and L-rhamnose, and are thought to be involved in carbon cycling in oceans (76).…”

In Situ Hydrogen and Nitrous Oxide as Indicators of Concomitant Fermentation and Denitrification in the Alimentary Canal of the EarthwormLumbricus terrestris

“…5). The hydrolysis of the plant heteropolymer hemicellulose typically yields the pentoses xylose and arabinose, the hexoses glucose, mannose, and galactose, and the disaccharide cellobiose (45), and fucose occurs in plant cell walls, bacterial extracellular polysaccharides, and animal glycoproteins (66). Thus, at least some of the monosaccharides detected in the earthworm gut might be derived from ingested biomass.…”