Benedetto Corain, C. Crotti, A. Del Prà, Fernando Filira, Giuseppe Zanotti,
... metalsB. Corain, C. Crotti, A. Del Pra, F. Filira, and G. ZanottiCite this: Inorg. Chem. 1981, 20, ...
Tópico(s): Carbon dioxide utilization in catalysis
1981 - American Chemical Society | Inorganic Chemistry
Benedetto Corain, A. Del Prà, Fernando Filira, Giuseppe Zanotti,
... nickel(II)B. Corain, A. Del Pra, F. Filira, and G. ZanottiCite this: Inorg. Chem. 1979, 18, ...
Tópico(s): Inorganic and Organometallic Chemistry
1979 - American Chemical Society | Inorganic Chemistry
Fernando Filira, Carlo Di Bello, Augusto C. Veronese, Ferruccio D’Angeli,
... from N-acetoacetyl derivatives of secondary amino acidsFernando Filira, Carlo Di Bello, Augusto C. Veronese, and Ferruccio ...
Tópico(s): Ferrocene Chemistry and Applications
1972 - American Chemical Society | The Journal of Organic Chemistry
Mati Fridkin, Haim Tsubery, Esther Tzehoval, A Vonsover, Laura Biondi, Fernando Filira, Raniero Rocchi,
The IgG-derived immunomodulating peptide tuftsin, Thr-Lys-Pro-Arg, is recognized by specific receptors on phagocytic cells, notably macrophages, and is capable of targeting proteins and peptides to these sites. Aiming to target 3′-azido-3′-deoxythymidine (AZT) to HIV-infected macrophages, a conjugate of AZT with tuftsin was synthesized. The AZT-tuftsin chimera possesses the characteristic capacities of its two components. Thus, like AZT, it inhibits reverse transcriptase activity and HIV-antigen ...
Tópico(s): T-cell and B-cell Immunology
2004 - Wiley | Journal of Peptide Science
Fernando Filira, Barbara Biondi, Laura Biondi, Elisa Giannini, Marina Gobbo, Lucia Negri, Raniero Rocchi,
The [D-Ala2]deltorphin I sequence in which the aspartic acid residue is replaced by the Nγ-OCH3-α,γ-diamino (S) butanoyl residue was synthesized using the Fmoc-chemistry-based solid phase procedure. The resulting deltorphin analogue was chemoselectively glucosylated by reaction with unprotected D-glucose (Glc). The Asn4-, (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)-Asn4- and the (2-acetamido-2-deoxy-D-galactopyranosyl)-Asn4-deltorphin I were also prepared for comparison. The affinity ...
Tópico(s): Carbohydrate Chemistry and Synthesis
2003 - Royal Society of Chemistry | Organic & Biomolecular Chemistry
Marina Gobbo, Laura Biondi, Fernando Filira, Renato Gennaro, Monica Benincasa, Barbara Scolaro, Raniero Rocchi,
Drosocin and apidaecin Ib are two insect antimicrobial peptides showing a significant sequence homology and a common mechanism of action, which includes stereoselective elements but is devoid of any pore-forming activity. A substantial difference between the two peptides is the presence in the drosocin sequence of an O-glycosylated threonine residue, which is important for its antimicrobial activity. Through the synthesis of a series of differently glycosylated drosocin analogues, we have shown ...
Tópico(s): Insect and Pesticide Research
2002 - American Chemical Society | Journal of Medicinal Chemistry
Roberto Corradini, Stefano Sforza, Arnaldo Dossena, Gerardo Palla, Raniero Rocchi, Ferdinando Filira, Flavia Nastri, Rosangela Marchelli,
Peptide nucleic acid (PNA) analogs based on Nα-(thymin-1-ylacetyl)ornithine were previously shown to form triplexes with complementary RNA. In order to obtain optically pure compounds for hybridization experiments, chiral monomers based on D- or L-ornithine, Nδ-Fmoc-Nα-(thymin-1-ylacetyl)ornithine 2 and Nδ-Fmoc-Nα-(uracil-1-ylacetyl)ornithine 3 were synthesized either by a one-step or by a simple three-step procedure starting from Nδ-protected ornithine; the latter procedure led to enantiomerically ...
Tópico(s): Advanced biosensing and bioanalysis techniques
2001 - Royal Society of Chemistry | Journal of the Chemical Society Perkin Transactions 1
... Medline 120M. Zheng, M. Gobbo, L. Biondi, F. Filira, S. Hakomori and R. Rocchi (1994). Synthetic immunochemistry ...
Tópico(s): Chemical Synthesis and Analysis
1999 - Wiley | Journal of Peptide Science
Laura Biondi, Fernando Filira, Marina Gobbo, Barbara Scolaro, Raniero Rocchi, F. CAVAGGION,
Syntheses are described of two new tuftsin derivatives containing a 2‐acetamido‐2‐deoxy‐D‐galac‐topyranosyl unit α‐ or β‐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 α]Thr‐OH and Fmoc‐[GalNAc(Ac) 3 β]Thr‐OH were allowed to react with H‐Lys(Z)‐Pro‐Arg(NO 2 )‐ ...
Tópico(s): Glycosylation and Glycoproteins Research
1991 - Wiley | International journal of peptide & protein research
Fernando Filira, Laura Biondi, Marina Gobbo, Raniero Rocchi,
Partial N-alkylation of amino acids was observed during hydrogenolytic deprotection.
Tópico(s): Glycosylation and Glycoproteins Research
1991 - Elsevier BV | Tetrahedron Letters
Fernando Filira, Laura Biondi, Barbara Scolaro, Maria Teresa Foffani, Stefano Mammi, Evaristo Peggion, Raniero Rocchi,
Sequential glycopeptides [Thr(beta-D-galactose)-Ala-Ala]n, with n ranging from 2 to 7, as models of natural antifreeze glycoproteins were synthesized by the continuous flow, solid phase procedure. The conformational properties of these materials in solution were investigated by c.d. and 1H-n.m.r. spectroscopy. In aqueous solution the c.d. pattern is practically independent of chain length and is very similar to that of natural antifreeze glycoproteins. The results are interpreted in terms of random ...
Tópico(s): RNA and protein synthesis mechanisms
1990 - Elsevier BV | International Journal of Biological Macromolecules
Fernando Filira, Laura Biondi, F. CAVAGGION, Barbara Scolaro, Raniero Rocchi,
Synthesis is described of four tuftsin derivatives containing a D-glucopyranosyl or a D-galactopyranosyl unit covalently linked to the hydroxy side chain function of the threonine residue through either an alpha or beta O-glycosidic linkage. Fmoc-threonine derivatives containing the suitable unprotected sugar were used for incorporating the O-glycosylated amino acid residue. Z-Thr[alpha-Glc(OBzl)4]-OBzl and Z-Thr[alpha-Gal(OBzl)4]-OBzl were prepared from the tetra-O-benzylated sugar and Z-Thr-OBzl ...
Tópico(s): Chemical Synthesis and Analysis
1990 - Wiley | International journal of peptide & protein research
Raniero Rocchi, Laura Biondi, F. CAVAGGION, Fernando Filira, Marina Gobbo, Shlomo Dagan, Mati Fridkin,
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. Glu 2 ‐rigin and D‐gluconyl‐Glu 2 ‐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 ...
Tópico(s): Chemical Synthesis and Analysis
1987 - Wiley | International journal of peptide & protein research
Ferruccio D’Angeli, Fernando Filira, Ernesto Scoffone,
The use of the N-acetoacetyl protecting group for N-terminal cysteine residue enabled creation of an efficient and mild one-pot native chemical ligation/SEA ligation sequence giving access to large cyclic peptides.
Tópico(s): Chemical Synthesis and Analysis
1965 - Elsevier BV | Tetrahedron Letters
Marina Gobbo, Laura Biondi, Fernando Filira, Barbara Scolaro, Raniero Rocchi, T. Piek,
Syntheses are described of some mono‐ and di‐glycosylated analogues of vespulakinin 1. The solid phase procedure, based on the Fmoc chemistry, was used to prepare (Gal α)Thr 3 ‐vespulakinin 1, (Galβ)Thr 3 ‐vespulakinin 1 and the di‐glycosylated analogue ((Gal α)Thr 3 . (Gal α)Thr 4 ‐vespulakinin 1. The β‐glycosylated derivative was also prepared by the continuous flow variant of the Fmoc polyamide method. The synthesized glycopeptides were purified and characterized by amino acid analysis, optical rotation, ...
Tópico(s): Glycosylation and Glycoproteins Research
1992 - Wiley | International journal of peptide & protein research
Mingjie Zheng, Marina Gobbo, Laura Biondi, Fernando Filira, Sen‐itiroh Hakomori, Raniero Rocchi,
Monoclonal antibody FDC‐6, and its second‐generation antibodies FDB‐1 and FDB‐4, are able to distinguish between fibronectin (FN) from fetal or cancer tissue (onco‐FN) vs. FN from normal adult tissue and plasma (nor‐FN). The epitope structure recognized by the above antibodies is the glycohexapeptide H‐Val‐(GalNAc‐α)Thr‐His‐Pro‐Gly‐Tyr‐OH ( P2 ). In order to define further the specificity of the reactive site, we synthesized various glycopeptides based on the unglycosylated hexapeptide sequence ( P1 ) and compared ...
Tópico(s): Peptidase Inhibition and Analysis
1994 - Wiley | International journal of peptide & protein research
Laura Biondi, Fernando Filira, Virgilio Giormani, Raniero Rocchi,
Bovine pancreatic ribonuclease A was reacted with D-gluconyl-glycine azide in aqueous solution at pH 8.9, in absence of phosphates. Five out of 11 amino groups can be reproducibly modified and the penta D-gluconyl-glycinated ribonuclease A had greater than 70% of the enzymic activity of the unmodified enzyme toward cytidine 2', 3'-cyclic phosphate as well as uridine 2', 3'-cyclic phosphate and yeast RNA. The kinetic parameters Km and k2 of the modified enzyme were calculated from double-reciprocal ...
Tópico(s): Biochemical and Molecular Research
1980 - Wiley | International journal of peptide & protein research
Marina Gobbo, Laura Biondi, Fernando Filira, Fernando Formaggio, Marco Crisma, Raniero Rocchi, Claudio Toniolo, Quirinus B. Broxterman, Johan Kamphuis,
Tópico(s): Machine Learning in Bioinformatics
1998 - Springer Science+Business Media | Letters in Peptide Science
Marina Gobbo, Laura Biondi, Fernando Filira, Raniero Rocchi, T. Piek,
Syntheses are described of two bradykinin‐like kinins isolated from Vespa analis (G‐R‐P‐P‐G‐F‐S‐P‐F‐R‐V‐I, VSK‐A) and Vespa tropica (G‐R‐P‐Hyp‐G‐F‐S‐P‐F‐R‐V‐V, VSK‐T) and of their cyclic analogues. Linear dodecapeptides were prepared by the solid‐phase procedure based on Fmoc‐chemistry, and cyclization was carried out by the diphenyl‐phosphorazide method. Peptides were characterized by amino acid analysis, optical rotation, analytical HPLC and FAB‐MS. The conformational features of the cyclic and ...
Tópico(s): Protein Hydrolysis and Bioactive Peptides
1995 - Wiley | International journal of peptide & protein research
Marina Gobbo, Laura Biondi, Fernando Filira, Raniero Rocchi, T. Piek,
Syntheses are described of some linear and cyclic kinin analogues. Cyclization, by the diphenyl‐phosphorazide method, of linear peptides prepared by the solid‐phase procedure based on Fmoc chemistry, was used for preparing cyclo‐bradykinin and cyclo‐kallidin (cyclo‐Lys‐bradykinin). Removal of the protecting group from the lysine side chain of cyclo‐kallidin followed by acylation with the N ‐terminal sequence of vespulakinin 1 (VSK l), Fmoc‐Thr(tBu)‐Ala‐Thr(tBu)‐Thr(tBu)‐Arg(Pmc)‐Arg(Pmc)‐Arg(Pmc)‐Gly‐ ...
Tópico(s): Asymmetric Synthesis and Catalysis
1994 - Wiley | International journal of peptide & protein research
Claudio Toniolo, Fernando Filira, Carlo Di Bello,
Abstract The Cotton effects of N ‐acetoacetyl amino acids and derivatives were examined by a circular dichroism technique. A correlation has been established between the sign of the Cotton effect and the absolute configuration of the asymmetric center. The L derivatives show, in dioxane, negative circular dichroism curves, whereas the D antipodes present positive curves. The effect of solvent and pH and influence of alkylation at the amide nitrogen are also discussed.
Tópico(s): DNA and Nucleic Acid Chemistry
1971 - Wiley | Biopolymers
Raniero Rocchi, Laura Biondi, Fernando Filira, Esther Tzehoval, Shlomo Dagan, Mati Fridkin,
Six Thr 1 (O‐glyco)‐derivatives of the “phagocytosis stimulating peptide” tuftsin, H‐Thr‐Lys‐Pro‐Arg‐OH and the N‐glycosylated undecapeptide H‐Thr‐Lys‐Pro‐Arg‐Glu‐Gln‐Gln‐Tyr‐Asn(β‐ d ‐GlcNAc)‐Ser‐Thr‐OH, which correspond to the “tuftsin‐region” at the Fc‐domain of immunoglobulin G (amino acid residues 289–299), were evaluated in comparison with tuftsin and rigin, H‐Gly‐Gln‐Pro‐Arg‐OH, for their capacity to evoke the release of interleukin‐1 and tumor necrosis factor from mouse peritoneal macrophages ...
Tópico(s): Neuropeptides and Animal Physiology
1991 - Wiley | International journal of peptide & protein research
Raniero Rocchi, Laura Biondi, Fernando Filira, Barbara Scolaro,
Synthesis of the carbohydrate‐free heptadecapeptide corresponding to the amino acid sequence of vespulakinin 1 was achieved by the continuous flow solid phase procedure on 4‐hydroxymethyl‐phenoxyacetyl‐norleucyl derivatized Kieselguhr‐supported polydimethylacrylamide resin, as well as by a combination of solid phase and solution syntheses. Preformed Fmoc‐amino acid symmetrical anhydrides (Boc derivative for the N ‐terminal residue) were used for amine acylation in the continuous flow method. Serine ...
Tópico(s): Enzyme function and inhibition
1987 - Wiley | International journal of peptide & protein research
Raniero Rocchi, Laura Biondi, Fernando Filira, Marina Gobbo, Shlomo Dagan, Mati Fridkin,
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(NO 2 )‐OBzl with D(+)‐gluco‐1,5‐lactone followed by catalytic hydrogenation gave N α‐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‐( N G ‐nitroargininamido)‐D‐glucopyranose followed by ...
Tópico(s): Diet, Metabolism, and Disease
1987 - Wiley | International journal of peptide & protein research
Laura Biondi, Fernando Filira, Marina Gobbo, Raniero Rocchi,
Stepwise solution syntheses are described of the homo-oligomers Z-(Thr)n-NHCH3 (n=1-4, I1-4), Z-¿[Gal(Ac)4beta]Thr¿n-NHCH3(n=1-5, II1-5) and Z-[(Galbeta)Thr]n-NHCH3 (n=1-5, III1-5). Members of the III1-5 series were obtained by de-acetylation of the corresponding oligomers of the II1-5 series. The conformational preferences of the terminally protected homo-peptides of the three series were investigated by FT-IR absorption spectroscopy both in the solid state and in CDCl3 solution, at various concentrations. ...
Tópico(s): Chemical Synthesis and Analysis
2002 - Wiley | Journal of Peptide Science
Laura Biondi, Fernando Filira, Raniero Rocchi, Esther Tzehoval, Mati Fridkin,
Syntheses are described of the Hyp 3 ‐tuftsin analogue and of its derivatives α‐ or β‐ O ‐glycosylated at the side chain function of the hydroxyproline residue. The carbohydrate‐free tetrapeptide was prepared by reacting Z‐Thr‐Lys(Z)‐OH with H‐Hyp‐Arg(NO 2 )‐OBzl by the mixed anhydride procedure. In the synthesis of the α‐glycosylated analogue the O ‐glycosyl amino acid was incorporated by reacting Boc‐(Glcα+β)Hyp‐OH with H‐Arg(NO 2 )‐OBzl through the same procedure. The α‐glucosylated dipeptide was isolated ...
Tópico(s): Glycosylation and Glycoproteins Research
1993 - Wiley | International journal of peptide & protein research
Bruno Filippi, Laura Biondi, Fernando Filira, Raniero Rocchi, Cecilia Bellini, Giampietro Sarto,
Abstract The synthesis in solution of some modified (D)Ala 2 ,Leu 5 ‐enkephalins has been carried out. The lipophilic properties of the parent compound have been modified by amidation of the carboxyl function with alkylamines of increasing hydrophilicity to increase permeability of the blood‐brain barrier. Attempts to reduce enzymatic degradation have been carried out either by reductive glucosamination or by amidation of the carboxyl function with 2‐amino‐2‐deoxy‐β‐D‐glucopyranose. Esterification ...
Tópico(s): Receptor Mechanisms and Signaling
1983 - Wiley | Biopolymers
Giuseppe Zanotti, Fernando Filira, Antonio Del Prà, Giorgio Cavicchioni, Augusto C. Veronese, Ferruccio D’Angeli,
α-Bromo-N-benzyl-propionamide and -isobutyramide react with sodium hydride yielding 2-amino-oxazolidinones. Dioxopiperazines are formed only from the halogeno-propionamide. The structure and stereochemistry of a 2-amino-oxazolidinone have been demonstrated by an X-ray crystal analysis. A cycloaddition onto an amide carbonyl is suggested in order to explain the formation of the oxazolidinone derivatives.
Tópico(s): Chemical Synthesis and Analysis
1980 - | Journal of the Chemical Society. Perkin transactions I/Journal of the Chemical Society. Perkin transactions. I
Carlo Di Bello, Fernando Filira, Virgilio Giormani, Ferruccio D’Angeli,
The acetoacetyl group allows quantitative retention of configuration in the synthesis of a peptide (valylvaline methyl ester) when suitable condensing agents such as dicyclohexylcarbodi-imide alone or in the presence of N-hydroxysuccinimide are used, and hydroxylamine hydrochloride in an acidic medium is the cleavage agent.
Tópico(s): Analytical Chemistry and Chromatography
1969 - Royal Society of Chemistry | Journal of the Chemical Society C Organic
Ferruocio D'Angeli, Ernesto Scoffone, Fernando Filira, Virgilio Giormani,
Tópico(s): Chemical Synthesis and Analysis
1966 - Elsevier BV | Tetrahedron Letters