C-Glycoside synthesis

We are interested in the synthesis of C-glycosyl amino acids, which are analogues of important compounds of glycopeptides. We have developed a direct method for the coupling of an amino acid fragment to the sugar fragment, using an amino acid-derived zinc reagent and triacetylglucal.

C-Glycoside synthesis

Key References

B.J. Dorgan and R.F.W. Jackson, Synlett, 1996, 859-861.

Conformational Studies

We have uncovered a most striking conformational effect in simple monosaccharides, in which the introduction of bulky silyl substituents leads to an unusual conformation in which four of the five ring substituents are axial.

conformational studies

Key References

C. Walford, R.F.W. Jackson, N.H. Rees, W. Clegg and S.L. Heath, Chem. Commun., 1997, 1855-1856