Preparation of Saccharin Derivatives of Amino Acids as Potential Peptidomimetic Building Blocks

Abstract

We present a useful route for the preparation of saccharin derivatives of amino acids. Sixteen new compounds, saccharin-derived amino acids, were synthesized, all of them bearing additional functional groups either at the 5- or 6-position of the saccharin skeleton, thus rendering the compounds more amenable to functionalization.

Keywords:

• Amino acid
• bidentate ligands
• oxidative cyclization
• peptidomimetic
• Saccharin

ACKNOWLEDGMENTS

This work was supported financially by the Slovenian Research Agency. The authors thank Roger Pain for his critical reading of the manuscript.

Notes

^a Reaction conditions: 1 equiv. of sulfonamide 1a, 7 equiv. of periodic acid, 7 equiv. of acetic acid anhydride, 5, 20, or 50 mol% CrO₃, 20 ml of solvent.

^b Dielectric constant.