Over the last decades chemical and biological investigations revealed a wide range of complex functions and mechanism where pectin is involved; for example, the cholesterol-lowering effect, plant cell defence mechanism or inhibition of the growth of metastases [1-3]. Therefore, to foster knowledge in this area chemical synthesis is asked to produce pectin fragments in defined structure and appreciable amounts.
Successfully established leaving groups for glycosylation reactions areN-phenyl tricloroacetimidates and thiophenols [4] shown by several working groups. We were able to synthesize galacturonate glycosyl donors3,5,6,7,8in presentable yields starting directly from galacturonic acid. Using orthogonal protecting group system the glycosyl donors were adapted for the synthesis of pectin fragments by modular design principle (MDP).
1. M. Ruth, A. S. Truswell,Amer. J. Clin. Nutr. 30, 171-175, 1977.
2. B. L. Ridley, M. A. O’Neill, D. Mohnen.Phytochem.57,929-967, 2001.
3. K.J. Pienta, H. Naik, A. Akhtar, K. Yamazaki,J Natl. Cancer Inst.87,348-353, 1995.
4. D. Magaud, C. Grandjean, A Doutheau, D Anker, V. Shevchik, N. Cotte-Pattat, J. Robert-Baudouy,Carbohydr. Res. 314, 189-199, 1998.
