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Action of rat liver Galβ1-4GlcNAc α(2-6)-sialyltransferase on Manβ1-4GlcNAcβ-OMe, GalNAcβ1-4GlcNAcβ-OMe, Glcβ1-4GlcNAcβ-OMe and GlcNAcβ1-4GlcNAcβ-OMe as synthetic substrates

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Abstract

Incubation of synthetic Man\1-4GlcNAcβ-OMe, GalNAcβ1-4GlcNAcβ-OMe, Glcβ1-4GlcNAcβ-OMe, and GlcNAcβ1-4GlcNacβ-OMe with CMP-Neu5Ac and rat liver Galβ1-4GlcNAc α(2-6)-sialyltransferase resulted in the formation of Neu5Acα2-6Manβ1-4GlcNAcβ-OMe, Neu5Acα2-6GalNAcβ1-4GlcNAcβ-OMe, Neu5Acα2-6Glcβ1-4GlcNAcβ-OMe and Neu5Acα2-6GlcNAcβ1-4GlcNAcβ-OMe, respectively. Under conditions which led to quantitative conversion of Galβ1-4GlcNAcβ-OEt into Neu5Acα2-6Galβ1-4GlcNAcβ-OEt, the aforementioned products were obtained in yields of 4%, 48%, 16% and 8%, respectively. HPLC on Partisil 10 SAX was used to isolate the various sialyltrisaccharides, and identification was carried out using 1- and 2-dimensional 500-MHz1H-NMR spectroscopy.

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Abbreviations

2D:

2-dimensional

CMP:

cytidine 5′-monophosphate

CMP-Neu5Ac:

cytidine 5′-monophospho-β-N-acetylneuraminic acid

COSY:

correlation spectroscopy

DQF:

double quantum filtered

HOHAHA:

homonuclear Hartmann-Hahn

MLEV:

composite pulse devised by M. Levitt

Neu5Ac:

N-acetylneuraminic acid

Neu5Ac2en:

2-deoxy-2,3-didehydro-N-acetylneuraminic acid

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Authors and Affiliations

  1. Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, PO Box 80.075, NL-3508 TB, Utrecht, The Netherlands

    Cornelis H. Hokke, Jos G. M. van der Ven, Johannis P. Kamerling & Johannes F. G. Vliegenthart

Authors
  1. Cornelis H. Hokke
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  2. Jos G. M. van der Ven
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  3. Johannis P. Kamerling
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  4. Johannes F. G. Vliegenthart
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Hokke, C.H., van der Ven, J.G.M., Kamerling, J.P. et al. Action of rat liver Galβ1-4GlcNAc α(2-6)-sialyltransferase on Manβ1-4GlcNAcβ-OMe, GalNAcβ1-4GlcNAcβ-OMe, Glcβ1-4GlcNAcβ-OMe and GlcNAcβ1-4GlcNAcβ-OMe as synthetic substrates. Glycoconjugate J 10, 82–90 (1993). https://doi.org/10.1007/BF00731191

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  • DOI: https://doi.org/10.1007/BF00731191

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