Fucosylation

Leukocyte adhesion deficiency, type II (MIM 266265) Probably mutations affecting a Golgi-located GDP-fucose transporter, resulting in defective fucosylation. 

N. P. J. Price, B. Relic, F. Talmont, A. Lewin, D. Pronie, S. G. Pueppke, F. Maillct, J. Denarie, J.-C. Prome, and W. J. Broughton, Broad-ho.st-range Rhizohiimi species strain NGR 234 secretes a family of carbamoylated, and fucosylated, nodulation signals that are O-acetylated or sulfated. Mol. Microbiol. 6 3575 (1992). 

J. Lorquin, G. Lortet, M. Ferro, N. Mear, B. Dreyfus, J.-C. Prome, and C. Boivin, Nod factors from Sinorhizobium saheli and 5. teranga bv. sesbaniae are both arabi-nosylated and fucosylated, a structural feature specific to Sesbania rostrata symbionts. Molec. Plant Microbe Interact. I0 il9 (1997). 

Sawa M, Hsu TL, Itoh T et al (2006) Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo. Proc Natl Acad Sci USA 103 12371-12376... 

Wisnewski, N., McNeil, M., Grieve, R.B. and Wassom, D.L. (1993) Characterization of novel fucosyl- and tyvelosyl-containing glycoconjugates from Trichinella spiralis muscle stage larvae. Molecular and Biochemical Parasitology 61, 25—36. 

Haslam, S.M., Coles, G.C., Munn, E.A., Smith, T.S., Smith, H.F., Morris, H.R. and Dell, A. (1996) Haemonchus contortus glycoproteins contain oligosaccharides with novel highly fucosylated core structures. Journal of Biological Chemistry 271, 30561-30570. 

A fourth family of A-glycans are referred to as hybrid glycans. These glycans share structural features of the high mannose and complex-type families. They usually retain two mannoses on the 6-arm of the trimannosyl core whilst complex-type antennae are elaborated on the 3-arm. Hybrid structures are frequentiy bisected and may also be core fucosylated (Fig. 15.1). It should be noted that whilst core fucosylation is common in complex-type, hybrid and truncated glycans, it is rarely found in high mannose glycans. 

Novel Fucosylated A/-glycan Core Structures in Haemonchus contortus... 

Fig. 15.5. Structures of A/-linked glycans from several different species of parasitic nematodes, illustrating both similarities with mammalian glycans (compare with Figs 15.1 and 15.2) and features unique to nematodes (e.g. tyvelose and PC capping and novel core fucosylation). The filarial nematode glycans are believed to be substituted with charged residues, which are not yet characterized.

Premier, C., Mach, L., Glossl, J. and Marz, L. (1992) The antigenicity of the carbohydrate moiety of an insect glycoprotein, honey-bee (Apis mellifera) venom phospholipase A2. The role of al,3-fucosylation of the asparagine-bound IV-acetylglucosamine. Bio chemicalJournal 284, 377-380. 

Ramirez-Soto, D. and Poretz, R.D. (1991) The (l-3)-linked (X-L-fucosyl group of the IV-glycans of the Wistaria floribunda lectins is recognised by a rabbit antiserum. Carbohydate Research 213, 27-36. 

These results encouraged the authors to attempt the synthesis of more-complex oligosaccharides, such as the Lex and Lea derivatives, 65 and 66, respectively. After formation of the (1 — 3)-fucosyl linkage, as promoted by HC104-Si02, in a stereo-and regio-selective manner, the peracetylated galactosyl trichloroacetimidate was added to afford the desired Lex derivative 65 in 62% yield. The same method was applied to obtain the Lea derivative 66 in 59% (Scheme 14).86... 

FIG. 58. Optimized C-fucosylated glycopeptides identified in a chemical library of 390,625 members produced by SPPS.374-375... 

Fig. 73. Galactosylated and/or fucosylated P. aeruginosa lectin ligands built on an AB2 scaffold/...

F. Morvan, A. Meyer, A. Jochum, C. Sabin, Y. Chevolot, A. Imberty, J.-P. Praly, J.-J. Vasseur, E. Souteyrand, and S. Vidal, Fucosylated pentaerythrityl phosphodiester oligomers (PePOs) Automated synthesis of DNA-based glycoclusters and binding to Pseudomonas aeruginosa lectin (PA-IIL), Biocon-jug. Chem., 18 (2007) 1637-1643. 

Similar results were recently obtained with a human monoclonal antibody, with KDEL sequences fused to the C-termini of both heavy chains, expressed in tobacco [33]. As observed for the invertase-HDEL fusion, about 90% of the N-linked glycans on this antibody were of the high-mannose type, with 6-9 mannose residues, while a fraction contained the immunogenic P(l,2)-xylose glyco-epitope (Fig. 15.6). However, this antibody was not a(l,3)-fucosylated, a glycan modification occurring in the trans Golgi [34]. 

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