Condensation reactions catalyzed by α-N-acetylgalactosaminidase from Aspergillus niger yielding α-N-acetylgalactosaminides

Abstract Extracellular α-N-acetylgalactosaminidase from Aspergillus niger catalyzed glycosylation yielding a series of 2-acetamido-2-deoxy-α-D-galactobiosides using 2-acetamido-2-deoxy-D-galactopyranose as a glycosyl donor. The isomers α-D-GalpNAc-(1→6)-D-GalpNAc, α-D-GalpNAc-(1→3)-D-GalpNAc and α-D-GalpNAc-(1→6)-D-GalfNAc were isolated and spectrally characterized. The purified enzyme was further used for the glycosylation of free amino acids (serine and threonine) and their N-(tert-butoxycarbonyl)-protected analogs to synthesize the Tn antigen (GalpNAc-α-O-Ser/Thr) and its N-(tert-butoxycarbonyl)-protected derivatives.

[1]  V. Křen,et al.  Induction, purification and characterization of α-N-acetylgalactosaminidase from Aspergillus Niger , 2008, Applied Microbiology and Biotechnology.

[2]  M. Przybylski,et al.  Glycal glycosylation and 2-nitroglycal concatenation, a powerful combination for mucin core structure synthesis. , 2007, The Journal of organic chemistry.

[3]  A. Vetere,et al.  Enzymatic synthesis of the Tn antigen , 2007 .

[4]  G. Boons,et al.  Comprehensive glycoscience : from chemistry to systems biology , 2007 .

[5]  A. M. Wu.  Carbohydrate Structural Units in Glycosphingolipids as Receptors for Gal and GalNAc Reactive Lectins , 2002, Neurochemical Research.

[6]  V. Křen,et al.  Reverse hydrolysis catalysed by β- N-acetylhexosaminidase from Aspergillus oryzae , 1997, Biotechnology Letters.

[7]  V. Křen,et al.  Fungal β-N-acetylhexosaminidases with high β-N-acetylgalactosaminidase activity and their use for synthesis of β-GalNAc-containing oligosaccharides , 2003 .

[8]  J. Duus,et al.  Carbohydrate structural determination by NMR spectroscopy: modern methods and limitations. , 2000, Chemical reviews.

[9]  Pierre Sinaÿ,et al.  Synthèse d'oligomères du polysaccharide capsulaire de Salmonella typhi, bactérie à l'origine de la fièvre typhoïde , 1999 .

[10]  K. Ajisaka,et al.  Purification of α-N-acetyl-galactosaminidase from Aspergillus niger and its use in the synthesis of GalNAc-α-(1→O)-serine , 1999 .

[11]  V. Havlíček,et al.  NKR-P1A protein, an activating receptor of rat natural killer cells, binds to the chitobiose core of uncompletely glycosylated N-linked glycans, and to linear chitooligomers. , 1997, Biochemical and biophysical research communications.

[12]  S. Bay,et al.  Enzymatic synthesis of some O-β-d-digalactosyl glycopeptides, using β-d-galactosidase , 1993 .

[13]  K. Ajisaka,et al.  Novel N-linked oligo-mannose type oligosaccharides containing an alpha-D-galactofuranosyl linkage found in alpha-D-galactosidase from Aspergillus niger. , 1992, Glycoconjugate journal.

[14]  P. Larsson,et al.  Enzymatic synthesis of monosaccharide-amino acid conjugates , 1991 .

[15]  S. Bay,et al.  Synthesis of alpha and beta-glycopyranosyl-serine derivatives by enzymic transglycosylation. , 1991, Biomedica biochimica acta.

[16]  Stephen J. Angyal,et al.  The composition of reducing sugars in solution , 1984 .

[17]  T. Nagayo,et al.  Isolation and characterization of a glycoprotein from a human rectal adenocarcinoma. , 1983, Journal of biochemistry.

[18]  H. Paulsen,et al.  Synthese der glycopeptide O-β-d-galactopyranosyl-(1→3)-O-(2-acetamido-2-desoxy-α-d-galactopyranosyl)-(1→3)-l-serin und -l-threonin , 1982 .

[19]  J. Imbach,et al.  A general method of synthesis and isolation, and an n.m.r-spectroscopic study, of tetra-O-acetyl-d-aldopentofuranoses , 1979 .

[20]  J. Touchstone.  Practice of Thin Layer Chromatography , 1978 .

[21]  H. Paulsen,et al.  Synthese von oligosaccharid-einheiten von blutgruppensubstanzen mit terminalen α-verknüpften D-Galactosamin-Gruppierungen☆ , 1977 .