Beilstein J. Org. Chem. 2010, 6, 699–703.
7. Zhi, Z.; Laurent, N.; Powell, A. K.; Karamanska, R.; Fais, M.;
Deprotection was also successful when the hydrogenation was
performed first, but in some cases migration of acetate to the
aminoethyl linker was observed. However, this can be avoided
by using palladium hydroxide on charcoal as the hydrogenation
catalyst, with short reaction times, followed by the immediate
use of the resulting amine in further coupling [18].
Voglmeir, J.; Wright, A.; Blackburn, J. M.; Crocker, P. R.;
Russell, D. A.; Flitsch, S. L.; Field, R. A.; Turnbull, J. E. ChemBioChem
8. Karamanska, R.; Clarke, J.; Blixt, O.; MacRae, J. I.; Zhang, J. Q.;
Crocker, P. R.; Laurent, N.; Wright, A.; Flitsch, S. L.; Russell, D. A.;
Field, R. A. Glycoconjugate J. 2008, 25, 69–74.
9. Laurent, N.; Voglmeir, J.; Wright, A.; Blackburn, J.; Pham, N. T.;
Wong, S. C. C.; Gaskell, S. J.; Flitsch, S. L. ChemBioChem 2008, 9,
Sialoside 19 was deprotected by treatment with NaOMe,
followed by LiOH and subsequent hydrogenation to give 9.
10.Laurent, N.; Haddoub, R.; Flitsch, S. L. Trends Biotechnol. 2008, 26,
Conclusion
11.Laurent, N.; Voglmeir, J.; Flitsch, S. L. Chem. Commun. 2008,
We have described rapid and convenient methods for the syn-
thesis of a range of aminoethyl glycosides (1–9) of common
mono- and disaccharides. Although some of the glycosylation
reactions could be improved by using alternative glycosylation
methods (such as trichloroacetimidates, thiols), these would
require more steps with chromatographic purifications and less
overall yields. These aminoethyl glycosides are now readily
accessible for incorporation into glycan arrays.
12.Laurent, N.; Haddoub, R.; Voglmeir, J.; Wong, S. C. C.; Gaskell, S. J.;
Flitsch, S. L. ChemBioChem 2008, 9, 2592–2596.
13.Ni, J.; Singh, S.; Wang, L.-X. Bioconjugate Chem. 2003, 14, 232–238.
14.Sanki, A. K.; Mahal, L. K. Synlett 2006, 455–459.
15.Orlandi, S.; Annuziata, R.; Benaglia, M.; Cozzi, F.; Manzoni, L.
17.Chernyak, A. Y.; Sharma, G. V. M.; Kononov, L. O.; Krishna, P. R.;
Levinsky, A. B.; Kochetkov, N. K.; Rama Rao, A. V. Carbohydr. Res.
18.Noble, G. T.; Flitsch, S. L.; Liem, K. P.; Webb, S. J.
Supporting Information
A Supporting Information containing all experimental
details and analytical data of all compounds described in
the article as well as their precursors is available.
Supporting Information File 1
Experimental procedures and analytical data
License and Terms
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Creative Commons Attribution License
permits unrestricted use, distribution, and reproduction in
any medium, provided the original work is properly cited.
Acknowledgements
We are grateful to the EPSRC, BBSRC, EC (Marie Curie ITN)
and Royal Society (Wolfson Merit Award to SLF) for funding.
The license is subject to the Beilstein Journal of Organic
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