Skip to main content
Log in

Efficient Enzymatic Synthesis of 4-methylumbelliferyl N-acetyllactosaminide and 4-methylumbelliferyl sialyl N -acetyllactosaminides Employing β-D-galactosidase and Sialyltransferases

  • Published:
Biotechnology Letters Aims and scope Submit manuscript

Abstract

4-Methylumbelliferyl N-acetyllactosaminide and 4-methylumbelliferyl sialyl N-acetyllactosaminides, which are used for the assay of sialytransferase, neuraminidase and fucosyltransferase, were synthesized, respectively, by the β-D-galactosidase from Bacillus circulans and by a recombinant rat α2,3-(N)-sialyltransferase or rat liver α2,6-(N)-sialyltransferase with CMP-N-acetylneuraminic acid as donor.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • T Angata A Varki (2002) ArticleTitleChemical diversity in the sialic acids and related α-keto acids: an evolutionary perspective Chem. Rev. 102 439–469

    Google Scholar 

  • E Farkas J Thiem (1999) ArticleTitleEnzymatic synthesis of galactose-containing disaccharides empolying β-galactosidase from Bacillus circulans Eur. J. Org. Chem. 3073 3077

    Google Scholar 

  • MC Galan AP Venot J Glushka A Imberty GJ Boons (2002) ArticleTitleα-(2,6)-Sialyltransferase-catalyzed sialylations of conformationally constrained oligosaccharides J. Am. Chem. Soc. 124 5964–5973

    Google Scholar 

  • T Hennet D Chui JC Paulson JD Marth (1998) ArticleTitleImmune regulation by the ST6Gal sialyltransferase Proc. Natl. Acad. Sci. USA 95 4504–4509

    Google Scholar 

  • Y Kajihara D Kamiyama N Yamamoto T Sakakibara M Izumi H Hashimoto (2004) ArticleTitleSynthesis of 2-[(2-pyridyl)amino]ethyl β-D-lactosaminide and evalution of its acceptor ability for sialyltransferase: a comparison with 4-methylumbelliferyl and dansyl β-D-lactosaminide Carbohydr. Res. 339 1545–1550

    Google Scholar 

  • Y Kanie A Kirsch O Kanie CH Wong (1998) ArticleTitleEnzymatic assay of galactosyltransferase by capillary electrophoresis Anal. Biochem. 263 240–245

    Google Scholar 

  • H Kodama LG Baum JC Paulson (1991) ArticleTitleSynthesis of linkage-specific sialoside substrates for colorimetric assay of neuraminidases Carbohydr. Res. 218 111–119

    Google Scholar 

  • G Limberg GC Slim CA Compston P Stangier MM Palcis RHJ Furneaux (1996) ArticleTitleA new assay for sialyltransferase using fluorescein-labelled acceptors Liebigs Ann. Chem. 1 1773–1784

    Google Scholar 

  • SJ Morris GE Price JM Barnett SA Hiscox H Smith C Sweet (1999) ArticleTitleRole of neuraminidase in influenza virus-induced apoptosis J. Gen. Virol. 80 137–146

    Google Scholar 

  • T Murata S Akimoto M Horimoto T Usui (1997) ArticleTitleGalactosyl transfer onto p-nitrophenyl β-D-glucoside using β-D-galactosidase from Bacillus circulans Biosci. Biotechnol. Biochem. 61 1118–1120

    Google Scholar 

  • JS Oxford P Novelli A Sefton R Lambkin (2002) ArticleTitleNew millennium antivirals against pandemic and epidemic influenza: the neuraminidase inhibitors Antivir. Chem. Chemother. 13 205–217

    Google Scholar 

  • S Sabesan JC Paulson (1986) ArticleTitleCombined Chemical and enzymatic synthesi of sialyloligosaccharides and characterization by 500-MHz 1H and 13C NMR spectroscopy J. Am. Chem. Soc. 108 2068–2080

    Google Scholar 

  • C Schaub B Muller RR Schmidt (1998) ArticleTitleNew sialyltransferase inhibitors based on CMP-quinic acid: development of a new sialyltransferase assay Glycoconjugate J. 15 345–354

    Google Scholar 

  • S Singh M Scigelova G Vic DHG Crout (1996) ArticleTitleGlycosidase-catalyzed oligosaccharide synthesis of di-, tri- and tetra-saccharides using the N-acetylhexosaminidase from Aspergillus oryzae and the β-D-galactosidase from Bacillus circulans J. Chem. Soc., Perkin Trans. 1 1921–1926

    Google Scholar 

  • T Usui S Kubota H Ohi (1993) ArticleTitleA convenient bn synthesis of β-D-galactosyl disaccharide derivatives using the β-D-galactosidase from Bacillus circulans Carbohydr. Res. 244 315–323

    Google Scholar 

  • T Usui S Morimoto Y Hayakawa M Kawaguchi T Murata Y Matahira Y Nishida (1996) ArticleTitleRegioselectivity of β-D-galactosyl-disaccharide formation using the β-D-galactosidase from Bacillus circulans Carbohydr. Res. 285 29–39

    Google Scholar 

  • JALM Dorst ParticleVan JM Tikkanen CH Krezdorn MB Streiff EG Berger JA Kuik ParticleVan JP Kamerling JF Vliegenthart (1996) ArticleTitleExploring the substrate specificities of α-2,6- and α-2,3-sialyltransferases using synthetic acceptor analogues Eur. J. Biochem. 242 674–681

    Google Scholar 

  • A Varki (1993) ArticleTitleBiological roles of oligosaccharides: all of the theories are correct Glycobiology 3 97–130

    Google Scholar 

  • KB Wlasichuk MA Kashem PV Nikrad P Bird C Jiang AP Venot (1993) ArticleTitleDetermination of the specificities of rat liver Galβ(1–4)GlcNAc α2,6-sialyltransferase and Galβ(1–3/4)GlcNAc α2,3-sialyltransferase using synthetic modified acceptors J. Biol. Chem. 268 13971–13977

    Google Scholar 

  • JY Zhao NJ Dovichi O Hindsgual S Gosselin MM Palcic (1994) ArticleTitleDetection of 100 molecules of product formed in a fucosyltransferase reaction Glycobiology 4 239–242

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Xiaoxiong Zeng.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zeng, X., Sun, Y. & Uzawa, H. Efficient Enzymatic Synthesis of 4-methylumbelliferyl N-acetyllactosaminide and 4-methylumbelliferyl sialyl N -acetyllactosaminides Employing β-D-galactosidase and Sialyltransferases. Biotechnol Lett 27, 1461–1465 (2005). https://doi.org/10.1007/s10529-005-1310-3

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10529-005-1310-3

Keywords

Navigation