W-Glycans

Stanley P, Raju TS, Bhaumik M. CHO cells provide access to novel W-glycans and developmentally regulated glycosyltransferases. Glycobiology 1996 6 696-699. 

Jonke S, Liu KG, Schmidt RR. Solid-phase oligosaccharide synthesis of a small library of W-glycans. Chem. Eur. J. 100. 2006 12 1274-1290. 

Mannose-6-phosphate on high-mannose-type W-glycans... 

With this system and the building blocks 19,28, and 45 shown in the scheme up to a branched hexasaccharide W-glycan was successfully obtained (11 steps on solid phase, 19% overall yield 86% per step) (see 34). This was a major improvement over the results reported in Scheme 4. A careful study of this reaction sequence revealed that the second glycosylation step is incomplete, thus leading also to byproduct formation (48). Therefore, a capping step of unreacted hydroxy groups based on benzoyl isocyanate reaction was introduced (25). As expected and shown in Scheme 11, this way clean product formation could be gained, however the overall yield was not increased. 

Scheme 16.16. Solid-supported synthesis of sialic acid containing W-glycan.

Huang W, Wang D, Yamada M, Wang LX (2009) Chemoenzymatic synthesis and lectin array characterization of a class of W-glycan clusters. J Am Chem Soc 131 17963-17971... 

Maras, M., Saelens, X., Laroy, W. et al. (1997) In vitro conversion of the carbohydrate moiety of fungal glycoproteins to mammalian-type oligosaccharides - evidence for JV-acetylglucosaminyltransferase-I-accepting glycans from Trichoderma reesei. European Journal of Biochemistry, 249 (3), 701-707. 

Harnett, W., Houston, KM., Amess, R. and Worms, M.J. (1993) Acanthocheilonema viteae. phosphorylcholine is attached to the major excretory-secretory product via a N-linked glycan. Experimental Parasitology 77, 498-502. 

Haslam, S.M., Houston, KM., Harnett, W., Reason, A.J., Morris, H.R. and Dell, A. (1999) Structural studies of phosphorylcholine-substituted A-glycans of filarial parasites conservation amongst species and discovery of novel chito-oligomers. Journal of Biological Chemistry 274, 20953-20960. 

Khoo, K.-H., Morris, H.R. and Dell, A. (1993) Structural characterisation of the major glycans of Toxocara canis ES antigens. In Lewis, J.W. and Maizels, R.M. (eds) Toxocara and Toxocariasis Clinical, Epidemiological and Molecular Perspectives. Institute of Biology, London, pp. 133-140. 

Leteux, C., Childs, R.A., Chai, W., Stoll, M.S., Kogelberg, H., and Feizi, T. (1998) Biotinyl-L-3-(2-naph-thyl)-alanine hydrazide derivatives of N-glycans Versatile solid-phase probes for carbohydrate-recognition studies. Glycobiology 8, 227-236. 

Tarendno, A.L., Phelan, A.W., and Plummer Jr., T.H. (1993) 2-Iminothiolane A reagent for the introduction of sulfhydryl groups into oligosaccharides derived from asparagine-linked glycans. Glycobiology 3, 279-285. 

K. Karaveg, A. Siriwardena, W. Tempel, Z.-J. Liu, J. Glushka, B.-C. Wang, and K. W. Moremen, Mechanism of class 1 (glycosylhydrolase family 47) a-mannosidases involved in iV-glycan processing and endoplasmatic reticulum quality control,./. Biol. Chem., 280 (2005) 16197-16207. 

F. Vallee, K. Karaveg, A. Herscovics, K. W. Moremen, and P. L. Howell, Structural basis for catalysis and inhibition of /V-glycan processing class I a-l,2-mannosidases, J. Biol. Chem., 275 (2000) 41287-41298. 

K. J. Gregg, W. F. Zandenberg, J.-H. Hehemann, G. E. Whitworth, L. Deng, D. J. Vocadlo, and A. B. Boraston, Analysis of a new family of widely distributed metal-independent a-mannosidases provides unique insight into die processing of TV-linked glycans, J. Biol. Chem., 286 (2011) 15586-15596. 

Fibers, I.J.W., Stoopen, G.M., Bakker, H., Stevens, L.H., Bardor, M., Molthoff, J.W., Jordi, W.J.R.M., Bosch, D., and Lommen, A. (2001). Influence of growth conditions and developmental stage on At-glycan heterogeneity of transgenic immunoglobulin G and endogenous proteins in tobacco leaves. Plant Physiol. 126 1314-1322. 

Rayon, C., Cabanes-Macheteau, M., Louteher-Bourhis, C., Salliot-Marie, L, Lemoine, J., Reiter, W.-D., Lerouge, P, andFaye, L. (1999). Characterization of A-glycans from Arabidopsis. Application to a fncose-deticient mntant. 

Friess, W., Zhou, W, and Groves, M.J. (1996). In vivo activity of collagen matrices containing PS1, an antineoplastic glycan, against murine sarcoma cells. Pharm. Sci., 2,121-124. 

Fukuda, M. N., K. A. Masri, A. Dell, L. Luzzatto, and K. W. Moremen, Incomplete synthesis of N-glycans in congenital dyserythropoietic anemia type II caused by a defect in the gene encoding a-mannosidase II. Proc. Natl. Acad. Sci. USA 87 7443-7447, 1990. 

Eberl, M., Langermans, J.A., Vervenne, R.A., Nyame, A.K., Cummings, R.D., Thomas, A.W., Coulson, P.S. and Wilson, R.A. (2001) Antibodies to glycans dominate the host response to schistosome larvae and eggs is their role protective or subversive Journal of Infectious Diseases 183, 1238-1247. 

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