A-acetylglucosaminyl transferases

An improved synthesis of the oximino-lactone derivative 63 ( PUGNAc ) in five steps from 2-acetamido-2-deoxy-a-D-glucopyranose tetraacetate has been described, the critical step being a low temperature oxidation of an acyclic aldose oxime intermediate to a cyclic oximino-lactone with NCS and DBU. " The D-xylono-l,5-lacatam oxime derivative 64 has been synthesized from an L-serinal derivative as a potential A-acetylglucosaminyl transferase inhibitor. ... 

Finally an A/-acetylglucosaminyl transferase adds a-A/-acetylglucosamine to C-2 of the second (outer) glucosyl residue, so completing the outer core, which is now ready to accept the O-antigenic side chain, that has been prefabricated quite separately (see below). 

Branched Pentasaccharides.-p-D-Glc/ NAc-(l ->2)-a-D-6-deoxy-Manp-( 1 ->6)-[P-d-GlcpNAc-(l->2)-a-D-4-deoxy-Maiyj-(l->3)]-P-D-Maiy7-0-(CH2)7CH3 has been prepared as part of a study of A/-acetylglucosaminyl transferase. The positions of the deoxy groups are chosen such that the compound should be mono-specific for GlcNAc transferase The synthesis... 

Geremia, R.A., Mergaert, P., Geelen, D., Van Montague, M. and Holsters, M. (1994) The NODC protein of Azorhizobium-caulinodans is an IV-acetylglucosaminyl-transferase. Proceedings of the National Academy of Sciences USA 91, 2669—2673. 

Togayachi A, Akashima T, Ookubo R, Kudo T, Nishihara S, Iwasaki H, Natsume A, Mio H, Inokuchi J, Irimiffa T, Sasaki K, Narimatsu H. Molecular cloning and characterization of UDP-GlcNAc lactosylceramide beta 1,3-N-acetylglucosaminyl-transferase (beta 3Gn-T5), an essential enzyme for the expression of HNK-1 and Lewis X epitopes on glycolipids. J. Biol. Chem. 2001 276 22032-22040. 

Kumar, R, Camphausen, R T, Sullivan, F X, Cumming, D A, Core2 p-l,6-Al-acetylglucosaminyl-transferase enzyme activity is critical for P-selectin glycoprotein hgand-1 binding to P-selectin, Blood, 88, 3872-3879, 1996. 

Fig. 3. Representative pathway for the biosynthesis of Asn-linked oligosaccharide. Biosynthesis starts in the rough endoplasmic reticulum and proceeds through the cis-, medial-, and trans-Golgi apparatus, before glycoprotein is secreted. Some of the enzymes involved are oligosaccharyl transferase (OST) a-glucosidase I II (aG I II) ER-mannosidase (aM) a-mannosidase I II (aM I II) N-acetylglucosaminyl transferase I II (GnT I II) fucosyl transferase (FucT) galactosyl transferase (GalT) sialyl transferase (ST). n-Gn O-Man -Glc V-Fuc A-Gal O-SA (adopted from [40])...

C18H33NO15 503.456 Partial struct, of naturally occurring asparagine linked oligosaccharides. Functions as a selective substrate in N-acetylglucosaminyl transferase assays. 

Harpaz, N., and H. Schachter, Control of glycoprotein synthesis. Processing of asparagine-linked oligosaccharides by one or more rat liver Golgi a-D-mannosidases dependent on the prior action of UDP-N-acetylglucosamine a-D-mannoside P 2-N-acetylglucosaminyl-transferase I, J. Biol Chem., 1980, 255, 4894-4902. 

A.S. Opat, H. Puthalakath, J. Burke, P.A. Gleeson, Genetic defect in N-acetylglucosaminyl-transferase I gene of a ricin-resistant baby hamster kidney mutant, Biochem J, 1998,336, 593 598. 

F. Reck, E. Meinjohanns, J. Tan, A.A. Grey, H. Paulsen, H. Schachter, Synthesis of pentasaccharide analogues of the N-glycan substrates of N-acetylglucosaminyltransferases III, IV and V using tetrasaccharide precursors and recombinant beta-(1 2) -N-acetylglucosaminyl-transferase II, Carbohyclr Res, 1995, 275, 22 1 229. 

A. Nishikawa, J. Gu, S. Fujii, N. Taniguchi, Determination of N-acetylglucosaminyl-transferases III, IV and V in normal and hepatoma tissues of rats, Biochim Biophys Acta Gen Subj, 1990, 1035, 313-318. 

H. Saito, A. Nishikawa, J.G. Gu, Y. Ihara, H. Soejima, Y. Wada, C. Sekiya, N. Niikawa, N. Taniguchi, CDNA Cloning and Chromosomal Mapping of Human N-Acetylglucosaminyl-transferase V, Biochem Biophys Res Commun, 1994, 198, 318-327. 

D.H. Van den Eijnden, H. Winterwerp, P. Smeeman and W.E.C.M. Schiphorst, Novikoff ascites tumor cells contain A-acetyllactosaminide pl->3 and pi—>6 V-acetylglucosaminyl-transferase activity. J. Biol. Chem., 1983, 258, 3435-3437. 

Hagopian A Eylar EH. Glycoprotein biosynthesis studies on the receptor specificity of the polypeptide N-acetylglucosaminyl-transferase from bovine submaxillary glands. Arch Biochem Biophys (1968) 128(2) 422-433. 

A 2-acetamido-4-amino-2,4-dideoxy-P-D-glucopyranosyl residue was synthesized and incorporated as the terminal residue of a trisaccharide glycoside, in connection with studies of the acceptor requirements of N-acetylglucosaminyl transferase A 2-acetaniido-4-aniino-2,3,4,6-tetradeoxy-a-D-jiy/t>-hexopyranosyl residue was incorporated into a trisacchaiide-ribitol-phosphate, the repeat unit of a Streptococcus pneumoniae polysaccharide. The synthesis of diamino-sugar 58 is covered in Section 2.8. 

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