O-Fucosylation

B. Macek, J. Hofsteenge, and J. Peter-Katalinic, Direct determination of glycosylation sites in O-fucosylated glycopeptides using nano-electrospray quadrupole time-of-flight mass spectrometry, Rapid Commun. Mass Spectrom., 15 (2001) 771-777. 

A. Gonzalez de Peredo, D. Klein, B. Macek, D. Hess, J. Peter-Katalinic, and J. Hofsteenge, C-mannosylation and O-fucosylation of thrombospondin type 1 repeats, Mol. Cell. Proteomics, 1 (2002) 11-18. 

Gonzalez de Peredo, A., Klein, D Macek, B., Hess, D., Peter-Katalinic, J., and Hofsteenge, J. (2002) C-mannosylation and O-fucosylation of thrombospodin type I repeats. Mol. Cell Proteomics 1, 11-18. 

M. Mormann, B. Macek, A. G. De Peredo, J. Hofsteenge, and J. P. Katalinic, Structural studies on protein O-fucosylation by electron capture dissociation, Int. J. Mass Spectrom., 234 (2004) 11-21. 

Lacto- N-difucohexaose (7% of the total oligosaccharides) has not yet been fully characterized, but it appears to be a di-O-fucosyl derivative of lacto-Af -tetraose in which the a-L-fucosyl residues are linked to C-2 of the terminal n-galactose residue (as in lacto-AT-fucopentaose I) and to C-4 of the 2-acetamido-2-deoxy-D-glucose residue (as in lacto-iV-fucopentaose II). ... 

Hietter, H, Schultz, M, Kunz, H, Solid-phase synthesis of a 36 amino acid O-fucosyl-peptide with the uncommon Thr-Fuc linkage, Synlett, 1219-1220, 1995. 

Elofsson, M, Roy, S, Salvador, L A, Kihlberg, J, Building blocks for glycopeptide synthesis preparation of a-O-fucosylated Fmoc serine and threonine in one step from L-fucose tetraacetate. Tetrahedron Lett., 37, 7645-7648, 1996. 

Wong et al. designed the 0-fucopeptides 79 and 80 (Figure 16.28), which contain a O fucosyl-aminocyclohexanol and a-O-fucosyl-L-threonine as core structures. In these inhibitors... 

Figure 5 Other types of O-linked glycosylation in eukaryotes, (a) O-Mannosylation (b) O-fucosylation (c) O-glucosylation (d) O-galactosylation.

Nothing was known about the appearance of O-fucosylated proteins until the early 90s. Then, the uncommon Fuc-Ser/Thr motif was found in the growth factor domains of several coagulation and fibrinolytic proteins [110]. The structure also occurs in a small serine protease inhibitor isolated from Locusta migratoria (83 Scheme 36) [111]. 

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