N-acetyl-D-lactosamine

FITG fluorescein isothiocyanate GlcNAc N-acetyl-D-glucosamine LacNAc N-acetyl-D-lactosamine and siaLacNAc sialyl-N-acetyllactosamine. Reproduced with permission from S.I. van Kasteren, S.J. Campbell, S. Serres, D.C. Anthony, N.R. Sibson and B.G. Davis, Proceedings of the National Academy of Sciences of the United States of America, 2009, 106, 1,18. 2009, United States National Academy of Sciences [88]... 

From nitro-sugars. - iV-Acetyl-lactosamine 30 and N-acetyl-cpt-lactosamine 31 were obtained as a manno-nch epimeric mixture on ozonolysis of the 2-acetamido-l-nitro-derivatives 29, obtained from 3-0-(p-D-galactosyl)-D-arabinose 28 (Scheme 8). The / a /io-isomer 32 could be obtained in 15% yield from 28), by direct crystallization. Treatment of the product mixture with aqueous ammonia gave a g/uco-rich mixture from which the g/oco-isomer 30 could be crystallized (32% yield from 28). Similar procedures applied to L-arabinose led to 2-acetamido-2-deoxy-L-mannose and - glucose... 

Following the enzymatic synthesis of CMP-Neu5Ac, isolated a2-6-sialyl-transferases could be used to introduce sialic acid to the N-acetyl lactosamine derivates a-f in position 6. This afforded a series of trisaccharide derivates Neu5Aca2-6 Gal l-4GlcNAc l-R. The unblocked trisaccharide a [55], the methyl glycoside b [56], the -Asn derivative c [57], the pentapeptide derivative d [58], the allyl e [59], and the pent-4-enyl glycoside f [48] can be prepared in convincing yields (Fig. 6). 

Bartsch D, Mai JK (1991) Distribution of the 3-fucosyl-N-acetyl-lactosamine (FAL) epitope in the adult mouse brain. Cell Tiss. Res., 263, 353-366. 

Treatment of l-0-(a-D-glucopyranosyl)-D-fructose with hydrogen fluoride in pyridine has afforded a l,T 2,2 dianhydride mixture with the fructose moiety in either the pyranose or furanose fonn. Some novel 1,6-anhydro-lactose derivatives for the synthesis of oligosaccharides containing N-acetyl-lactosamine residues are mentioned in Chapter 4, and a 3,6-anhydroglucofuranose derivative resulting from an unusual molecular rearrangement of a xanthate is described in Chapter 7. 

In the second family of A -linked oligosaccharides, the two terminal D-mannose residues of the core pentasaccharide are substituted by a variable number of N-acetyl-lactosamine O-Gal-1 4-GlcNAc) units. The position of substitution of the A-acetyl-lactosamine can be (1 2), (1 4), and/or (1 6). This structural... 

Pierce, R. J., G. Spik, and J. Montreuil, Demonstration and cytosolic location of an endo-N-acetyl-(3-D-glucosaminidase activity towards an asialo-N-acetyl-lactosaminic-type substrate in rat liver, Biochem. J., 1980,185, 261-264. 

Durch Abbau des Disaccharids mit Ninhydrin, bei dem 3-D-Galakto-pyranosyl-D-arabinose erhalten wurde, bewiesen F. Zilliken, P. N. Smith, R. M. Tomarelli und P. Gyorgy (279) ebenfalls, daB A-Acctyl-lactosamin vorliegt. Auch das A-Acetyl-lactosamin wird, ebenso wie die isomere Lacto-A-biose I, von Lactase nicht angegriffen (250). 

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