Synthesis and Semisynthesis of Some Structural Elements of Oligo-Mannose Type N-Glycoproteins

Abstract For the construction of N-glycoprotein glycan chains, valuable potential glycosyl donors, O-α-D-mannopyranosyl-(1→2)-α-D-mannopyranose octaacetate (19) and O-α-D-mannopyranosyl-(1→2)-O-α-D-mannopyranosyl-(1→2)-α-D-mannopyranose undeca-acetate (20) were obtained in gram-scale by the acetylation and subsequent partial acetolysis of baker's yeast, without the isolation of mannan. The acetolytic products were investigated by matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry. Octaacetates of mannobiose (1→3) (11) and (1→6) (17) were chemically synthesized.

[1]  L. Jánossy,et al.  Synthesis and semisynthesis of a-d-mannopyranosyl-(1 ? 2)-a-d-mannopyranose octaacetate , 1996 .

[2]  C. Unverzagt.  Chemoenzymatic Synthesis of a Sialylated Undecasaccharide–Asparagine Conjugate , 1996 .

[3]  S. Ley,et al.  Synthesis of the Nonamannan Residue of a Glycoprotein with High Mannose Content , 1996 .

[4]  Y. Nakahara,et al.  Rationally designed syntheses of high-mannose and complex type undecasaccharides. , 1996, Carbohydrate research.

[5]  J. Kamerling,et al.  Synthesis of a fucosylated and a non-fucosylated core structure of xylose-containing carbohydrate chains from N-glycoproteins. , 1994, Carbohydrate research.

[6]  A. Lipták,et al.  Synthesis of some partially substituted methyl α-d- and phenyl 1-thio-α-d-mannopyranosides for the preparation of manno-oligosaccharides , 1994 .

[7]  J. Kamerling,et al.  Synthesis of a selectively protected trisaccharide building block that is part of xylose-containing carbohydrate chains from N-glycoproteins. , 1993, Carbohydrate research.

[8]  W. Günther,et al.  Synthesis of β-D-mannosides from β-D-glucosides via an intramolecular SN2 reaction at C-2 , 1992 .

[9]  H. Paulsen,et al.  Synthese einer verzweigten pentasaccharid-sequenz der “bisected” struktur von N-glycoproteinen☆ , 1990 .

[10]  J. Kamerling,et al.  Synthesis of four structural elements of xylose-containing carbohydrate chains from N-glycoproteins. , 1989, Carbohydrate research.

[11]  O. Hindsgaul,et al.  Substrates for the differentiation of the N-acetylglucosaminytransferases. Synthesis of βDGlcNAc(1 → 2)αDMan(1 → 6)βDMan and βDGlcNAc(1 → 2)αDMan(1 → 6) [αDMan(1 → 3)]βDMan glycosides , 1986 .

[12]  R. Jain,et al.  A synthesis of methyl 3-O-α-d-mannopyranosyl-α-d-mannopyranoside and related disaccharides , 1986 .

[13]  K. Matta,et al.  Lysosomal-enzyme targeting: the phosphorylation of synthetic D-mannosyl saccharides by UDP-N-acetyl-glucosamine:lysosomal-enzyme N-acetylglucosamine-phosphotransferase from rat-liver microsomes and fibroblasts. , 1986, Carbohydrate research.

[14]  Setsuzo Tejima,et al.  Syntheses of Acetylated Tetrasaccharides, Manα1→2Manα1→3Manβ1→4GlcNAc and Manα1→3Manα1→6Manβ1→4GlcNAc , 1984 .

[15]  T. Nukada,et al.  Synthesis of a nonahexosyl unit of a complex type of glycan chain of a glycoprotein. , 1983, Carbohydrate research.

[16]  P. Nánási,et al.  Synthesis of O-α- d-mannopyranosyl-(1→2)-O-α- d-mannopyranosyl-(1→2)- d-mannose, the repeating unit of the O8-antigen of Escherichia coli , 1983 .

[17]  F. Winnik,et al.  Syntheses of model oligosaccharides of biological significance. 2. Synthesis of a tetramannoside and of two lyxose-containing trisaccharides , 1982 .

[18]  Hisao. Yamamoto,et al.  Synthesis of linear d-mannotetraose and d-mannohexaose, partial structures of the cell-surface d-mannan of Candida albicans and Candida utilis , 1982 .

[19]  J. Arnarp,et al.  Synthesis of a nonasaccharide containing terminal N-acetyl-β-D-lactosaminyl residues, part of the ‘complex-type’ carbohydrate moiety of glycoproteins , 1982 .

[20]  T. Ogawa,et al.  Synthesis of a branched d-mannopentaoside and a branched d-mannohexaoside: Models of the outer chain of the glycan of soybean agglutinin , 1981 .

[21]  J. Jacquinet,et al.  Synthesis of blood-group substances. Part 11. Synthesis of the trisaccharide O-α-D-galactopyranosyl-(1 → 3)-O-β-D-galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-D-glucopyranose , 1981 .

[22]  M. Matsui,et al.  Synthetic studies on cell surface glycans 31: Branching pentasaccharides of glycoprotein , 1981 .

[23]  T. Ogawa,et al.  Reconstruction of glycan chains of glycoprotein , 1981 .

[24]  N. K. Kochetkov,et al.  Synthesis of 1,2-trans-disaccharides via sugar thio-orthoesters , 1980 .

[25]  R. R. Schmidt,et al.  Einfache Synthese von α-und β-O-Glykosylimidaten; Herstellung von Glykosiden und Disacchariden† , 1980 .

[26]  J. Arnarp,et al.  Synthesis of hepta- and penta-saccharides, part of the complex-type carbohydrate portion of glycoproteins , 1980 .

[27]  C. Reichert.  Synthesis of p-nitrophenyl 2-O-α-D-mannopyranosyl-α-D-mannopyranoside and p-nitrophenyl 6-O-α-D-mannopyranosyl-α-D-mannopyranoside , 1979 .

[28]  P. Nánási,et al.  Hydrogenolysis of dioxolane-type benzylidene derivatives: a convenient preparation of methyl 2-O-benzyl- and 3-O-benzyl-4,6-O-benzylidene-α-d-mannopyranoside , 1979 .

[29]  M. Matsui,et al.  Regio- and stereo-controlled synthesis of core oligosaccharides of glycopeptides , 1978 .

[30]  M. Ponpipom.  Synthesis of 3-O Substituted D-Mannoses , 1977 .

[31]  P. Gorin.  Rationalization of Carbon-13 Magnetic Resonance Spectra of Yeast Mannans and Structurally Related Oligosaccharides , 1973 .

[32]  S. Peat,et al.  765. The polysaccharides of baker's yeast. Part V. A further study of the mannan , 1961 .

[33]  P. Gorin,et al.  THE CONFIGURATION OF GLYCOSIDIC LINKAGES IN OLIGOSACCHARIDES: III. O-α-D-MANNOPYRANOSYL-(1 → 2)-O-α-D-MANNOPYRANOSYL-(1 → 2)-D-MANNOSE , 1957 .