The iminosugar conjugates according to the invention are N-alkylated 1,5-dideoxy-1,5-iminohexitol or 1,5-dideoxy-1,5-iminopentitol derivatives. The iminosugar component can be, for example, D- gluco -, L- ido -, D- galacto -, D -manno -, 2-acetamido-2-deoxy-D- gluco - or xylo -configuration. The N-substituent is a protected L-α-aminoacid derivative, showing L-lysine-like structural features. The linkage between the carbohydrate and the peptide component is not via the usual glycosidic position, but shows structural features of a very stable tertiary amine. Thus the linkage is very stable. These new compounds are synthesised by using catalytic intramolecular reductive amination of dicarbonyl sugars with partially protected amino acids. The process of intramolecular reductive amination itself is carried out using Pearlman's catalyst (Pd(OH) 2 /C) and H 2 at ambient pressure and room temperature.
The resulting accessible class of iminosugar conjugate compounds is represented by the general structure shown in Figure 4(c). The alkyl chain length parameter n can be freely chosen from n=0 upwards. Preferably n is between 0 and 10, and more preferably n is 2, 3, or 4. Residue R 1 can be chosen from H, OH, or NHAc, with Ac being Acetyl. R 2 can be H, OH, or NHAc. R 3 , R 4 , R 5 , R 6 can be H or OH. R 7 and R 8 can be H, CH2OH CH3, COQH, or COOR with R being Alkyl or Aryl. R 9 and R 10 can be chosen from H, NH 2 , NHR, with R being a protective group, an amino acid, a peptide, or a protein. R 11 can be OH, O-Alkyl, O-Aryl, NH 2 , N-Alkyl, N-Aryl, amino acid or peptide, connected via an amide bond.