Synthesis of glycosylated tuftsins and tuftsin-containing IgG fragment undecapeptide.

  title={Synthesis of glycosylated tuftsins and tuftsin-containing IgG fragment undecapeptide.},
  author={Laura Biondi and Fernando Filira and Marina Gobbo and Barbara Scolaro and Raniero Rocchi},
  journal={International journal of peptide and protein research},
  volume={37 2},
Syntheses are described of two new tuftsin derivatives containing a 2-acetamido-2-deoxy-D-galactopyranosyl unit alpha- or beta-glycosidically linked to the threonine's hydroxy side chain function and of the glycosylated undecapeptide corresponding to the tuftsin region of the heavy chain of IgG (amino acid sequence 289-299). The glycosylated tuftsins were synthesized by the solution procedure. Fmoc-[Gal NAc(Ac)3 alpha]Thr-OH and Fmoc-[GalNAc(Ac)3 beta]Thr-OH were allowed to react with H-Lys(Z… Expand
19 Citations
Solution synthesis of the glyco-hexapeptide sequence of the human oncofetal fibronectin defined by monoclonal antibody FDC-6.
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Synthesis and biological activity of [L‐hydroxyproline]3‐tuftsin analogue and its α‐ or β‐O‐D‐glucosylated derivatives
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Four Major Histocompatibility Complex (MHC) Class I binding glycopeptides and two peptide analogues, from a cytotoxic T-lymphocyte (CTL) epitope of Sendai Virus Nucleoprotein, have been preparedExpand
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Chapter 4 Chemical Synthesis of Glycopeptides
Publisher Summary This chapter discusses the chemical synthesis of glycopeptides. Glycoproteins are composed of a polypeptide backbone which is glycosylated with one or more carbohydrate chains. TheExpand
Novel glycosylated VIP analogs: synthesis, biological activity, and metabolic stability
  • D. Dangoor, B. Biondi, +4 authors R. Rocchi
  • Chemistry, Medicine
  • Journal of peptide science : an official publication of the European Peptide Society
  • 2008
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[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
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Being a totally synthetic, low-molecular weight, and carrier-free immunogen, the lipopeptide conjugate could be a prototype of synthetic carbohydrate vaccines. Expand
O-glycosyl α-amino acids as building blocks for glycopeptide synthesis
Abstract A review of O -glycosyl α-amino acid structures representing most of the glycosylation sites of known O -glycoproteins found in nature, their preparation by chemical methods and applicationExpand


Synthesis of modified tuftsins containing monosaccharides or monosaccharide derivatives.
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 by catalytic hydrogenation and trifluoroacetic acid treatment. 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, conformation, and biological activity of the carbohydrate-free vespulakinin 1.
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Synthesis of 2-acetamido-2-deoxyglucosylasparagine glyco-tripeptides and -pentapeptides by selective C- and N-terminal elongation of the peptide chain.
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2,3,4,6-Tetra-O-acetyl-1-N-[N-(tert-butyloxycarbonyl)-L-aspart-4-oyl]-D-g lucopyranosylamine and 2-acetamido-3,4,6-tri-O-acetyl-1-N-[N-(tert-butyloxycarbonyl)-L-aspart-4-oyl]-2Expand
Some further studies on the synthesis of glycopeptide derivatives: 2-acetamido-2-deoxy-beta-D-glucopyranosylamine derivatives.
The isolation, characterization and properties of two by-products in the preparation of 2-acetamido-3,4,6-tri-O- acetyl-2-deoxy-beta-d-glucopyranosylamine are described and conditions are given for their preparation in high yield. Expand
The azidonitration of tri-O-acetyl-D-galactal
Reaction of 3,4,6-tri-O-acetyl-D-galactal with excess ceric ammonium nitrate and sodium azide in acetonitrile produced 2-azido-1-nitrate addition products (53% β-galacto, 22% α-galacto, and 8%Expand
Studies on amino sugars I. Preparation of N-acyl derivatives of 2-acetamido-2-deoxy-beta-D-glycosylamine.
2-Acetamido-2-deoxy-3, 4, 6-tri-O-acetyl-β-D-glucosylamine was prepared by the hydrogenation of the corresponding p-nitrobenzamido derivative over Adams' catalyst. Expand
Synthese der glycopeptide O-β-d-galactopyranosyl-(1→3)-O-(2-acetamido-2-desoxy-α-d-galactopyranosyl)-(1→3)-l-serin und -l-threonin
Abstract In the presence of silver carbonate-silver perchlorate and dichloromethane-toluene as solvent, 3,4,6-tri- O -acetyl-2-azido-2-deoxy-β- d -galactopyranosyl chloride, and derivatives of lExpand
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