V-acetyllactosamine

Glycan array allows for the definition of fine differences in specificity among related lectins giving clues about the basis for differences in their biological activities. For example comparison of a set of human galectins demonstrated that Gal-1, Gal-2, and Gal-3 all bind /V-acetyllactosamine but... 

EC 2.4.1.90 /V-Acetyllactosamine synthase UDP-galactose + iV-acetyl-D-glucosamine UDP Af-acetyllactosamine Golgi apparatus ... 

Synthesis of Derivatives of V-acetyllactosamine from Lactal Hexa-acetate. Hexa-0-acetyl-2-deoxy-2-phthalimido-/l-D-lactosyl Chloride, R. U. Lemieux, S. Z. Abbas, H. M. Burzynska, and R. M. Ratcliffe, Can. J. Chem., 60 (1982) 63-67. 

Fig. 9. Synthesis of /V-acetyllactosamin (LacNAc, 7) with pl-4 galactosidase. The thermodynamic approach (reverse hydrolysis) involves D-galactose (5) as donor and /V-acctyl-D-glucosanminc (6) as acceptor substrate. Activated galactosyl donors (8-10) are used in the kinetic approach (trans-glycosylation)...

H Chemical Shifts of Structural-reporter Groups of Constituent Monosaccharides for Glycopeptides of the. V-Acetyllactosamine Type... 

Mong TK-K, Huang C-Y, Wong C-H. A new reactivity-based one-pot synthesis of V-acetyllactosamine oligomers. J. Org. 

Ujita M, Fukuda M. Regulation of poly-V-acetyllactosamine biosynthesis in O-glycans. Trends Glycosci. Glycotech. 2001 13(70) 177-191. 

Sasaki K, Kurata-Miura K, Ujita M, Angata K, Nakagawa S, Sekine S, Nishi T, Fukuda M. Expression cloning of cDNA encoding a human P-l,3-Ai-acetylglucosaminyltransferase that is essential for poly-V-acetyllactosamine synthesis. Proc. Natl. Acad. Sci. U.S.A. 1997 94(26) 14294-14299. 

Zhou DP, Dinter A, Gallego RG, Kamerhng JP, Vliegenthart JFG, Berger EG, Hennet T. A f -l,3-Ai-acetylglucosaminyltrans-ferase with poly-V-acetyllactosamine synthase activity is sfiuc-turally related to P-l,3-galactosyltransferases. Proc. Natl. Acad. Sci. U.S.A. 1999 96(2) 406-411. 

Torii T, Fukuta M, Habuchi O. Sulfation of sialyl V-acetyllactosamine oligosaccharides and fetuin oligosaccharides by keratan sulfate Gal-6-sulfotransferase. Glycobiology 2000 10(2) 203-211. 

This polysaccharide is structurally a poly-(/V-acetyllactosamine) chain, as seen... 

The structure of some of these oligosaccharides has been determined. A major N-glycan representing about 45% of the carbohydrate chains is a monosialylated monofucosylated diantennary glycan of the V-acetyllactosaminic type (Fig. 12A)[81]. A tetraantennary glycan of the V-acetyllactosaminic type has also been isolated and its structure determined by methylation analysis and 500MHz H-NMR (Fig. 12B)[82]. The major O-glycan of human vWf was shown to be a diantennary tetrasaccharide (Fig. 12C)[83]. 

Fig. 11.1-2 (a) Structure of S-type lectin, galectin-3, bound to /V-acetyllactosamine and... 

Several fucosyltransferases have been isolated and used for in vitro synthesis. The Lewis A al,4-fucosyltransferase transfers unnatural fucose derivatives in from their GDP esters [23]. The enzyme al,3-fucosyltransferase has been used to L-fucosylate the 3-posi-tion of the GlcNAc of iV-acetyllactosamine and of sialyl a2,3-/V-acetyllactosamine [24]. Several acceptor substrates with modifications in the GlcNAc residue could also be... 

Additional precursors in the use of the above strategy were prepared under two concise synthetic routes as outlined in Scheme 14. In the first approach, p-nitrophenyl thiolactoside 19 and /V-acetyllactosamine derivative 63 were used as starting... 

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