Synthesis and biological activity of tuftsin and rigin derivatives containing monosaccharides or monosaccharide derivatives
Article first published online: 12 JAN 2009
© 1987 Munksgaard International Publishers Ltd.
International Journal of Peptide and Protein Research
Volume 29, Issue 2, pages 262–275, February 1987
How to Cite
ROCCHI, R., BIONDI, L., CAVAGGION, F., FILIRA, F., GOBBO, M., DAGAN, S. and FRIDKIN, M. (1987), Synthesis and biological activity of tuftsin and rigin derivatives containing monosaccharides or monosaccharide derivatives. International Journal of Peptide and Protein Research, 29: 262–275. doi: 10.1111/j.1399-3011.1987.tb02253.x
- Issue published online: 12 JAN 2009
- Article first published online: 12 JAN 2009
- Received 29 May, accepted for publication 23 July 1986
- binding assays;
- glycosylated rigins;
- peptide synthesis in solution;
Synthesis of some modified rigins is described in which either D-gluconic acid or 2-amino-2-deoxy-β-D-glucopyranose have been linked to the parent molecule through amide bonds involving the α-amino function, α-carboxyl function or the γ-amide function of glutamine in position 2. Glu2-rigin and D-gluconyl-Glu2-rigin have also been synthesized. Binding and phagocytosis assays have been carried out on the rigin derivatives and on some glycosylated tuftsin derivatives as well. Of all the tested peptides only rigin enhanced the phagocytic capacity of mouse peritoneal macrophages to the same extent as tuftsin. The peptides H-Thr-Lys-Pro-Arg-NH-Glc and Nα-gluconyl-Gly-Glu-Pro-Arg-OH slightly enhanced phagocytosis. H-Thr[(α + β)-O-glucosyl]-Lys-Pro-Arg-OH was found to displace 3H-tuftsin even better than tuftsin but lacked the ability to stimulate phagocytosis.