1-fucose glycopeptides

E. M. V. Johansson, E. Kolomiets, F. Rosenau, K.-E. Jaeger, T. Darbre, and J.-L. Reymond, Combinatorial variation of branching length and multivalency in a large (390, 625 member) glycopeptide dendrimer library Ligands for Fucose-specific lectins, New J. Chem., 31 (2007) 1291-1299. 

In fact, other studies have shown that TMSOTf catalyzes the glycosylation of a silylated acceptor with a silylated hemiacetal donor [49]. Nudel man s procedure was applied to the synthesis [1-glucuronide 30, isolated in 57% yield. Kiyoi and Kondo have applied the TMSOTf activation protocol to protected L-fucose hemiacetal donors for glycopeptide synthesis and obtained glycopeptide fragment 31 in 74% yield (a p, 20 1) [50], Posner and Bull have developed a procedure that uses excess TMSOTf in the presence of molecular sieves (SYLOSIV A4) to synthesize various l.l -linked disaccharides such as the galactopyranose dimer 32 [51,52]. 

Studies have shown that the o -l,3-fucose residue does not play any role in the interaction between LCA and glycopeptides isolated from human LTF or chemically synthesized (Kornfeld et al. 1981). However, the same work showed that a-l,6-fucose is important for a tight binding. Also, X-ray diffraction studies have proved that the cy-1,6 fucose is essential for attaining the proper binding conformation of the carbohydrates (Bourne et al. 1993). 

One of the most characteristic differences between papain and the other sulfhydryl proteases, ficin and bromelain, is the absence of carbohydrate in papain. Glycopeptides have been isolated from ficin (48) and bromelain (49, 50, 51, 52). In the case of bromelain the carbohydrate moiety composed of mannose, xylose, fucose, and N-acetylglucosamine is covalently linked to an asparagine residue of the peptide chain through a glucosamine component of the sugar moiety (51,52). 

Peters, S, Lowary, T L, Hindsgaul, O, Meldal, M, Bock, K, Sohd-phase synthesis of a fucosylated glycopeptide of human factor IX with a fucose-a-(l-0)-serine linkage, J. Chem. Soc. Perkin Trans. 1, 3017-3022, 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. 

---