Novel glycosynthons for glycoconjugate preparation: oligosaccharylpyroglutamylanilide derivatives

Bioconjugate Chemistry
Christophe QuétardM Monsigny

Abstract

The reducing sugar of an oligosaccharide reacting with the alpha-amino group of an amino acid is converted to an N-oligosaccharylamino acid which can then be stabilized by N-acylation. Oligosaccharides in solution in N,N-dimethylformamide reacted with alpha-glutamyl-p-nitroanilide at 50 degrees C for a few hours, leading to an N-oligosaccharylglutamyl-p-nitroanilide. Then, the gamma-carboxylic group of the glutamyl moiety, activated by adding (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), reacted with the substituted alpha-amino group of the glutamyl residue, leading to an N-oligosaccharylpyroglutamyl-p-nitroanilide within 0.5 h. Such a one-pot two-step reaction was shown to be very efficient in the case of a disaccharide such as lactose, or pentasaccharides such as lacto-N-fucopentaoses, Lewis(a) or Lewis(x). The glycosynthons were characterized by chromatography (HPAEC and HPLC); their molecular mass was determined by electrospray ionization mass spectrometry, and the glycosylamides were shown to have a beta-anomeric configuration on the basis of their proton NMR. The N-oligosaccharylpyroglutamyl-p-nitroanilides are quite stable at room temperature over a large pH range. They are easily conver...Continue Reading

References

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Citations

Feb 14, 2002·Chemical Reviews·Benjamin G Davis
Aug 22, 2000·European Journal of Biochemistry·S CottazH Driguez
Dec 25, 2007·Oligonucleotides·Zhaoyang YeRam I Mahato
Jun 6, 2008·Expert Opinion on Drug Delivery·Juan M IracheSocorro Espuelas
Oct 24, 2012·Proteomics. Clinical Applications·Shuang Yang, Hui Zhang
Jan 10, 2017·Chembiochem : a European Journal of Chemical Biology·Klaus VilladsenMikkel B Thygesen
Aug 10, 2000·Analytical Biochemistry·K G Rice
May 24, 2006·Carbohydrate Research·Kim LarsenKnud J Jensen
Mar 7, 2007·Journal of the American Chemical Society·Nour Eddine FahmiSidney M Hecht

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