Synthesis of modified tuftsins containing monosaccharides or monosaccharide derivatives.

  title={Synthesis of modified tuftsins containing monosaccharides or monosaccharide derivatives.},
  author={Raniero Rocchi and Laura Biondi and Fernando Filira and Marina Gobbo and Shlomo Dagan and Mati Fridkin},
  journal={International journal of peptide and protein research},
  volume={29 2},
Synthesis of some modified tuftsins is described in which a monosaccharide or a monosaccharide derivative was incorporated in the molecule. Acylation of H-Thr-Lys(Z)-Pro-Arg(NO2)-OBzl with D(+)-gluco-1,5-lactone followed by catalytic hydrogenation gave N alpha-gluconyl-tuftsin. Glycosylation of the carboxyl function of the C-terminal arginine has been achieved by reacting, through the mixed anhydride procedure, Boc-Thr-Lys(Z)-Pro-OH with 2-deoxy-2-(NG-nitroargininamido)-D-glucopyranose followed… Expand
11 Citations
Synthesis of O-glycosylated tuftsins by utilizing threonine derivatives containing an unprotected monosaccharide moiety.
The resulting glycosylated tuftsin derivatives were fully deblocked by catalytic hydrogenation, purified by HPLC, and characterized by optical rotation, amino acid analysis, and 1H NMR. Expand
Synthesis and biological activity of tuftsin and rigin derivatives containing monosaccharides or monosaccharide derivatives.
Of all the tested peptides only rigin enhanced the phagocytic capacity of mouse peritoneal macrophages to the same extent as tuftsin, and H-Thr[(alpha + beta)-O-glucosyl]-Lys-Pro-Arg-OH was found to displace 3H-tuftsin even better than tuft sin but lacked the ability to stimulate phagocytes. Expand
Synthesis of glycosylated tuftsins and tuftsin-containing IgG fragment undecapeptide.
Two new tuftsins derivatives containing a 2-acetamido-2-deoxy-D-galactopyranosyl unit alpha- or beta-glycosidically linked to the threonine's hydroxy side chain function and the glycosylated undecapeptide corresponding to the tuftsin region of the heavy chain of IgG are described. Expand
Synthesis and biological activity of [L‐hydroxyproline]3‐tuftsin analogue and its α‐ or β‐O‐D‐glucosylated derivatives
Syntheses are described of the Hyp3-tuftsin analogue and of its derivatives alpha- or beta-O-glycosylated at the side chain function of the hydroxyproline residue. The carbohydrate-free tetrapeptideExpand
[6] Solid-phase synthesis of O-glycopeptides
Publisher Summary To study the influence of carbohydrate variation on the properties of a peptide or a protein, it has become important to have access to several different glycoforms. This can beExpand
Synthesis and biological activity of tuftsin, its analogue and conjugates containing muramyl dipeptides or nor‐muramyl dipeptides
The analogues of tuftsin turned out to be efficient stimulators of TNFα and IL6 secretion by monocytes and lymphocytes and did not affect the viability of the leukocyte population used in the experiments. Expand
Glyco-tuftsin derivatives modulate interleukin-1 and tumor necrosis factor production.
Several glycosylated tuftsin derivatives were found to modulate, in a rather dose-dependent manner, the release of the two cytokines from both cell types. Expand
Enhanced phagocytosis activity of cyclic analogs of tuftsin.
The enhanced potency of ctuf-G and one isomer of cTuf-D may be due to conformational effects and/or to the possibility that these cyclic peptides are resistant to proteolytic degradation. Expand
Tuftsin: its chemistry, biology, and clinical potential.
  • M. Fridkin, V. Najjar
  • Chemistry, Medicine
  • Critical reviews in biochemistry and molecular biology
  • 1989
The features of tuftsin, coupled with its low toxicity, make the peptide an attractive candidate for immunotherapy and its capacity to augment cellular activation is mediated by specific receptors that were identified, characterized, and recently isolated from rabbit peritoneal granulocytes. Expand
Tuftsin: On the 30-year anniversary of Victor Najjar’s discovery
The occurrence of tuftsin and retro-tuftsin sequences in proteins, their synthesis and biology, the antigenic properties of tuFTsin, its influence on phagocytic cells, and other biologic activities of Tuftsin, including antimicrobial, antiviral, antitumor and central effects are presented. Expand


Synthesis and biological activity of tuftsin and of [O = C Thr1]-tuftsin. A novel synthetic route to peptides containing N-terminal L -O = C Thr and L - O = C Ser residues.
The reaction was applied to the synthesis of [O = C Thr1] tuftsin, an active analog of the phagocytosis stimulating peptide tuft sin, and a new synthetic route to tuftSin is also described. Expand
Allongement de la cha⌝ne peptidique du côté c-terminal d'un glycosylaminoacide
Abstract An O-glycodipeptide was synthesized by lengthening the peptide chain on the C-terminal side of a glycosylamino acid unit. N -(Benzyloxycarbonyl)-3- O -(2,3,4,6-tetra- O -acetyl-β- DExpand
Un nouvel agent de glycosylation: l'anhydride trifluorométhanesulfonique. Synthèse des α et β O-glycosyl-L-sérine, -L-thréonine et -L-hydroxyproline
When 2,3,4,6-tetra-O-benzyl-D-glucopyranose, -D-galactopyranose and 2,3,4-tri-O-benzyl-D-xylopyranose were allowed to react in the cold in dichloromethane or acetonitrile as solvent in the presenceExpand
Studies on Peptides. XLVIII. Application of the Trifluoromethanesulphonic Acid Procedure to the Synthesis of Tuftsin
Trifluoromethanesulphonic acid removed all protecting groups from Z-Thr-Lys (Z)-Pro-Arg (Tos)-OH to give the phagocytosis-stimulating tetrapeptide, H-Thr-Lys-Pro-Arg-OH, named tuftsin. To thisExpand
Tuftsin and some analogs: synthesis and interaction with human polymorphonuclear leukocytes.
Taftsin and to a lesser extent [Lys1]tuftsin and [Ser 1]tuftssin were found to stimulate phagocytosis, whereas the other analogs synthesized as well as [Ser1] Tuftsin exhibited inhibitory effects to tuftsin's action. Expand
Tuftsin, Thr-Lys-Pro-Arg
Research indicates that tuftsin binding to target cells effect intracellular calcium and cyclic nucleotide levels, and implications of these facts on tuft sin’s mode of action are discussed. Expand
Synthesis of tuftsin and its analogs.
Tuftsin, a phagocytosis stimulating peptide, was synthesized according to a liquid phase method together with its four analogs, H–Thr–Arg–Pro–Arg–OH (2), H–Thr–Lys–Pro–Lys–OH (3),Expand
Rapid chromatographic technique for preparative separations with moderate resolution
(11) Potassium ferricyanide has previously been used to convert w'c-1,2-dicarboxylate groups to double bonds. See, for example, L. F. Fieser and M. J. Haddadln, J. Am. Chem. Soc., 86, 2392 (1964).Expand
Quantitative chromatographic methods for the study of enzymic transpeptidation reactions.
A colorimetric ninhydrin method has been applied to the quantitative estimation of amino acids and peptides on paper chromatograms. This method is suitable for the analysis of enzymicExpand
Partial sequences of histones with tuftsin activity.
Tuftsin and six tuftsin analogues with the partial sequences of histones were synthesized by the classical method and possess a high phagocytosis-stimulating activity on polymorphonuclear neutrophils from guinea pig. Expand