Lanthionine Peptides by S-Alkylation with Substituted Cyclic Sulfamidates promoted by Activated Molecular Sieves: Effects of the Sulfamidate Structure on the Yield (209 views visite)
J Org Chem (ISSN: 0022-3263linking), 2019 Nov 15; 84(22): 14957-14964.
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Paper type Tipo di articolo: Journal Article
Impact factor: 4.745, 5-year impact factor Impact factor a 5 anni: 4.176
Url: Not available. Non disponibile.
Keywords Parole chiave: Not available. Non disponibili.
Affiliations Affiliazioni:
*** IBB - CNR ***
Institute of Biostructures and Bioimaging , National Research Council , 80134 Naples , Italy.
Department of Science and Technologic Innovation Universita del Piemonte Orientale "A. Avogadro" , 15121 Alessandria , Italy.
Departamento de Quimica, Centro de Investigacion en Sintesis Quimica , Universidad de La Rioja , 26006 Logrono , Spain.
CIC bioGUNE , Bizkaia Technology Park, Building 800 , 48170 Derio , Spain.
References Riferimenti:
Not available. Non disponibili.
J Org Chem (ISSN: 0022-3263linking), 2019 Nov 15; 84(22): 14957-14964.
Export to Esporta in BibTeX Export to Esporta in EndNote
Paper type Tipo di articolo: Journal Article
Impact factor: 4.745, 5-year impact factor Impact factor a 5 anni: 4.176
Url: Not available. Non disponibile.
Keywords Parole chiave: Not available. Non disponibili.
Affiliations Affiliazioni:
*** IBB - CNR ***
Institute of Biostructures and Bioimaging , National Research Council , 80134 Naples , Italy.
Department of Science and Technologic Innovation Universita del Piemonte Orientale "A. Avogadro" , 15121 Alessandria , Italy.
Departamento de Quimica, Centro de Investigacion en Sintesis Quimica , Universidad de La Rioja , 26006 Logrono , Spain.
CIC bioGUNE , Bizkaia Technology Park, Building 800 , 48170 Derio , Spain.
References Riferimenti:
Not available. Non disponibili.
Lanthionine Peptides by S-Alkylation with Substituted Cyclic Sulfamidates promoted by Activated Molecular Sieves: Effects of the Sulfamidate Structure on the Yield
A green and efficient method for preparing lanthionine peptides by a highly chemoselective and stereochemically controlled procedure is presented. It involves an S-alkylation reaction, promoted by activated molecular sieves, on chiral cyclic sulfamidates, both N-protected and unprotected. Of note, the reaction yield was high also for cyclic sulfamidates bearing a free amine group, while other strategies failed to achieve a ring-opening nucleophilic reaction with N-unprotected substrates. To prove the feasibility of the procedure, the synthesis of a thioether ring B mimetic of the natural lantibiotic haloduracin beta was performed.
A green and efficient method for preparing lanthionine peptides by a highly chemoselective and stereochemically controlled procedure is presented. It involves an S-alkylation reaction, promoted by activated molecular sieves, on chiral cyclic sulfamidates, both N-protected and unprotected. Of note, the reaction yield was high also for cyclic sulfamidates bearing a free amine group, while other strategies failed to achieve a ring-opening nucleophilic reaction with N-unprotected substrates. To prove the feasibility of the procedure, the synthesis of a thioether ring B mimetic of the natural lantibiotic haloduracin beta was performed.
Lanthionine Peptides by S-Alkylation with Substituted Cyclic Sulfamidates promoted by Activated Molecular Sieves: Effects of the Sulfamidate Structure on the Yield
Lanthionine Peptides by S-Alkylation with Substituted Cyclic Sulfamidates promoted by Activated Molecular Sieves: Effects of the Sulfamidate Structure on the Yield
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Mulliri S, Laaksonen A, Spanu P, Farris R, Farci M, Mingoia F, Roviello GN, Mocci F
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Verdoliva V, Digilio G, Saviano M, De Luca S
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Calce E, Digilio G, Menchise V, Saviano M, De Luca S
* Chemoselective Glycosylation of Peptides through S-Alkylation Reaction (691 visite) (PDF 155 visite)
Chemistry (ISSN: 1521-3765electronic, 0947-6539linking), 2018 Apr 20; 24(23): 6231-6238.
Impact Factor: 5.476
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Martinez-fernandez L, Pepino AJ, Segarra-marti J, Jovaisaite J, Vaya I, Nenov A, Markovitsi D, Gustavsson T, Banyasz A, Garavelli M, Improta R
* Photophysics of Deoxycytidine and 5-Methyldeoxycytidine in Solution: A Comprehensive Picture by Quantum Mechanical Calculations and Femtosecond Fluorescence Spectroscopy (222 visite)
J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 0002-7863print), 2017 Jun 14; 139(23): 7780-7791.
Impact Factor: 14.357
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Roviello GN, Iannitti R, Palumbo R, Simonyan H, Vicidomini C, Roviello V
* Lac-L-TTA, a novel lactose-based amino acid-sugar conjugate for anti-metastatic applications (278 visite)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2017 May 06; 49(8): 1347-1353.
Impact Factor: 2.906
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Calce E, De Luca S
* The Cysteine S-Alkylation Reaction as a Synthetic Method to Covalently Modify Peptide Sequences (377 visite)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2016 Aug 19; 22: 1-11.
Impact Factor: 5.317
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Vullo D, Supuran CT, Scozzafava A, De Simone G, Monti SM, Alterio V, Carta F
* Kinetic and X-ray crystallographic investigations of substituted 2-thio-6-oxo-1, 6-dihydropyrimidine-benzenesulfonamides acting as carbonic anhydrase inhibitors (231 visite)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391), 2016 Aug 15; 24(16): 3643-3648.
Impact Factor: 2.93
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Calce E, De Luca S
* Microwave heating in peptide side chain modification via cysteine alkylation (308 visite)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2016 Jun 28; 48: 2267-2271.
Impact Factor: 3.173
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Mishra CB, Kumari S, Angeli A, Monti SM, Buonanno M, Prakash A, Tiwari M, Supuran CT
* Design, synthesis and biological evaluation of N-(5-methyl-isoxazol-3-yl/1, 3, 4-thiadiazol-2-yl)-4-(3-substitutedphenylureido) benzenesulfonamides as human carbonic anhydrase isoenzymes I, II, VII and XII inhibitors (268 visite)
J Enzyme Inhib Med Chem, 2016; 17: 1-6.
Impact Factor: 3.428
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Desplat V, Vincenzi M, Lucas R, Moreau S, Savrimoutou S, Pinaud N, Lesbordes J, Peyrilles E, Marchivie M, Routier S, Sonnet P, Rossi F, Ronga L, Guillon J
* Synthesis and evaluation of the cytotoxic activity of novel ethyl 4-[4-(4-substitutedpiperidin-1-yl)]benzyl-phenylpyrrolo[1, 2-a]quinoxaline-carboxylate derivatives in myeloid and lymphoid leukemia cell lines (545 visite)
Eur J Med Chem (ISSN: 0223-5234, 1768-3254, 0223-5234linking), 2016; 113: 214-227.
Impact Factor: 4.519
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Calce E, Leone M, Mercurio FA, Monfregola L, De Luca S
* Solid-Phase S-Alkylation Promoted by Molecular Sieves (238 visite)
Org Lett (ISSN: 1523-7060, 1523-7052, 1523-7052electronic), 2015 Nov 20; 17(22): 5646-5649.
Impact Factor: 6.732
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Saghyan AS, Simonyan HM, Petrosyan SG, Geolchanyan AV, Roviello GN, Musumeci D, Roviello V
* Thiophenyl-substituted triazolyl-thione L-alanine: asymmetric synthesis, aggregation and biological properties (456 visite)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2014 Oct; 46(10): 2325-2332.
Impact Factor: 3.293
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Esposito L, Banyasz A, Douki T, Perron M, Markovitsi D, Improta R
* Effect of C5-methylation of cytosine on the photoreactivity of DNA: A joint experimental and computational study of TCG trinucleotides (281 visite)
J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 0002-7863print), 2014 Sep 6; 136(31): 10838-10841.
Impact Factor: 12.113
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Oppermann S, Schrader FC, Elsasser K, Dolga AM, Kraus AL, Doti N, Wegscheid-Gerlach C, Schlitzer M, Culmsee C
* Novel N-Phenyl-Substituted Thiazolidinediones Protect Neural Cells against Glutamate- and tBid-Induced Toxicity (486 visite)
J Pharmacol Exp Ther (ISSN: 0022-3565, 1521-0103), 2014 Sep; 350(2): 273-289.
Impact Factor: 3.972
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Calce E, Leone M, Monfregola L, De Luca S
* Lipidated Peptides Via Post-Synthetic Thioalkylation Promoted By Molecular Sieves (438 visite)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2014; 46(8): 1899-1905.
Impact Factor: 3.293
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Sica F, Pica A, Merlino A, Russo Krauss I, Ercole C, Picone D
* The multiple forms of bovine seminal ribonuclease: Structure and stability of a C-terminal swapped dimer (292 visite)
Febs Lett (ISSN: 0014-5793, 0014-5793print, 1873-3468electronic), 2013 Nov 29; 587(23): 3755-3762.
Impact Factor: 3.341
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Calce E, Leone M, Monfregola L, De Luca S
* Chemical Modifications Of Peptide Sequences Via S-Alkylation Reaction (309 visite)
Org Lett (ISSN: 1523-7060, 1523-7052, 1523-7052electronic), 2013; 15(20): 5354-5357.
Impact Factor: 6.324
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Monfregola L, Leone M, Calce E, de Luca S
* Postsynthetic modification of peptides via chemoselective N-alkylation of their side chains (426 visite)
Org Lett (ISSN: 1523-7060, 1523-7052, 1523-7052electronic), 2012 Apr 6; 14(7): 1664-1667.
Impact Factor: 6.142
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Monfregola L, De Luca S
* Synthetic strategy for side chain mono-N-alkylation of Fmoc-amino acids promoted by molecular sieves (466 visite)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2011 Oct; 41(4): 981-990.
Impact Factor: 3.248
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Milite C, Castellano S, Benedetti R, Tosco A, Ciliberti C, Vicidomini C, Boully L, Franci G, Altucci L, Mai A, Sbardella G
* Modulation of the activity of histone acetyltransferases by long chain alkylidenemalonates (LoCAMs) (323 visite)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 1464-3391electronic), 2011 Jun 15; 19(12): 3690-3701.
Impact Factor: 2.921
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Di Fiore A, Maresca A, Alterio V, Supuran CT, De Simone G
* Carbonic anhydrase inhibitors: X-ray crystallographic studies for the binding of N-substituted benzenesulfonamides to human isoform II (324 visite)
Chem Commun (ISSN: 1359-7345, 1364-548x, 1364-548xelectronic), 2011; 47(42): 11636-11638.
Impact Factor: 6.169
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Banyasz A, Karpati S, Mercier Y, Reguero M, Gustavsson T, Markovitsi D, Improta R
* The peculiar spectral properties of amino-substituted uracils: A combined theoretical and experimental study (287 visite)
J Phys Chem B (ISSN: 1520-6106, 1520-5207, 1520-5207electronic), 2010 Oct 7; 114(39): 12708-12719.
Impact Factor: 3.603
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Roviello GN, Gröschel S, Pedone C, Diederichsen U
* Synthesis of novel MMT/acyl-protected nucleo alanine monomers for the preparation of DNA/alanyl-PNA chimeras (370 visite)
Amino Acids (ISSN: 1438-2199, 0939-4451, 1438-2199electronic), 2010 May; 38(5): 1301-1309.
Impact Factor: 4.106
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Kaczmarek K, Farina B, Zubrzak P, Jankowski S, Zimecki M, Suder P, Benedetti E, Fattorusso R, Saviano M, Zabrocki J
* Synthesis, conformational analysis and immunological activity of β3Phe-substituted Cyclolinopeptide A analogues (440 visite)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2009 Mar; 15(3): 166-174.
Impact Factor: 1.807
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Hilvo M, Baranauskiene L, Salzano AM, Scaloni A, Matulis D, Innocenti A, Scozzafava A, Monti SM, Di Fiore A, De Simone G, Lindfors M, Janis J, Valjakka J, Pastorekova S, Pastorek J, Kulomaa MS, Nordlund HR, Supuran CT, Parkkila S
* Biochemical characterization of CA IX, one of the most active carbonic anhydrase isozymes (398 visite)
Jbc Papers (ISSN: 0021-9258, 1083-351x, 0021-9258linking), 2008 Oct 10; 283(41): 27799-27809.
Impact Factor: 5.52
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Leese MP, Jourdan FL, Gaukroger K, Mahon MF, Newman SP, Foster PA, Stengel C, Regis-Lydi S, Ferrandis E, Di Fiore A, De Simone G, Supuran CT, Purohit A, Reed MJ, Potter BVL
* Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents (397 visite)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2008 Mar 13; 51(5): 1295-1308.
Impact Factor: 4.898
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Grasso G, Rizzarelli E, Spoto G
* AP/MALDI-MS complete characterization of the proteolytic fragments produced by the interaction of insulin degrading enzyme with bovine insulin (480 visite)
J Mass Spectrom (ISSN: 1076-5174, 1096-9888), 2007 Dec; 42(12): 1590-1598.
Impact Factor: 3.062
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Leese MP, Leblond B, Smith A, Newman SP, Di Fiore A, De Simone G, Supuran CT, Purohit A, Reed MJ, Potter BVL
* 2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity (819 visite)
J Med Chem (ISSN: 0022-2623print, 0022-2623linking, 1520-4804), 2006 Dec 28; 49(26): 7683-7696.
Impact Factor: 5.115
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Saporito A, Marasco D, Chambery A, Botti P, Monti SM, Pedone C, Ruvo M
* The chemical synthesis of the GstI protein by NCL on a X-Met site (597 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2006 Dec 5; 83(5): 508-518.
Impact Factor: 2.48
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Vaccaro M, Accardo A, Tesauro D, Mangiapia G, Loef D, Schillen K, Soederman O, Morelli G, Paduan L
* Supramolecular aggregates of amphiphilic gadolinium complexes as blood pool MRI/MRA contrast agents: Physicochemical characterization (367 visite)
Langmuir (ISSN: 0743-7463), 2006 Jul 18; 22(15): 6635-6643.
Impact Factor: 3.902
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De Capua A, Goodman M, Amino Y, Saviano M, Benedetti E
* Conformation analysis of aspartame-based sweeteners by NMR spectroscopy, molecular dynamics simulations, and X-ray diffraction studies (595 visite)
Chembiochem (ISSN: 1439-4227, 1439-7633, 1439-7633electronic), 2006 Feb; 7(2): 377-387.
Impact Factor: 4.1
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Sica F, Di Fiore A, Zagari A, Mazzarella L
* The unswapped chain of bovine seminal ribonuclease: Crystal structure of the free and liganded monomeric derivative (302 visite)
Proteins (ISSN: 0887-3585, 1097-0134, 1097-0134electronic), 2003 Sep 1; 52(2): 263-271.
Impact Factor: 4.313
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Peggion C, Formaggio F, Crisma M, Toniolo C, Jimenez AI, Cativiela C, Kaptein B, Broxterman QB, Saviano M, Benedetti E
* Folding of peptides characterized by c3Val, a highly constrained analogue of valine (376 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2003; 68(2): 178-191.
Impact Factor: 2.733
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Romanelli A, Garella I, Menchise V, Iacovino R, Saviano M, Montesarchio D, Didierjean C, Lello PD, Rossi F, Benedetti E
* Crystal-state conformation of Cα, α-dialkylated peptides containing chiral β-homo-residues (401 visite)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2001; 7(1): 15-26.
Impact Factor: 1.451
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Pavone V, Lombardi A, Saviano M, De Simone G, Nastri F, Maglio O, Omote Y, Yamanaka Y, Yamada T
Conformational behavior of C(α, α)-diphenyl glycine: Extended conformation in tripeptides containing consecutive Dφg residues (366 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2000 Feb; 53(2): 161-168.
Impact Factor: 2.405
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De Simone G, Lombardi A, Galdiero S, Nastri F, Di Costanzo L, Gohda S, Sano A, Yamada T, Pavone V
The crystal structure of a Dcp-containing peptide (423 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2000 Feb; 53(2): 182-188.
Impact Factor: 2.405
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Lombardi A, De Simone G, Galdiero S, Nastri F, Di Costanzo L, Makihiara K, Yamada T, Pavone V
The crystal structure of Afc-containing peptide (386 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2000 Feb; 53(2): 150-160.
Impact Factor: 2.405
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Pavone V, Lombardi A, Saviano M, Nastri F, Zaccaro L, Maglio O, Pedone C, Omote Y, Yamanaka Y, Yamada T
Conformational Behaviour Of C (alpha, Alpha)-Diphenylglycine: Folded Vs. Extended Structures In Dphig-Containing Tripeptides (421 visite)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 1998 Feb; 4(1): 21-32.
Impact Factor: 1.311
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Gatos M, Formaggio F, Crisma M, Valle G, Toniolo C, Bonora GM, Saviano M, Iacovino R, Menchise V, Galdiero S, Pedone C, Benedetti E
Conformational Characterization Of Peptides Rich In The Cycloaliphatic C Alpha, Alpha-Disubstituted Glycine 1-Aminocyclononane-1-Carboxylic Acid (404 visite)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 1997 Sep; 3(5): 367-382.
Impact Factor: 1.311
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Pavone V, Lombardi A, Saviano M, Di Blasio B, Nastri F, Fattorusso R, Zaccaro L, Maglio O, Yamada T, Omote Y
Mixed conformation in C(α, α)-disubstituted tripeptides: X-ray crystal structures of Z-Aib-Dph-Gly-OMe and Bz-Dph-Dph-Gly-OMe (365 visite)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1994 Dec; 34(12): 1595-1604.
Impact Factor: 2.425
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Pavone V, Di Blasio B, Lombardi A, Maglio O, Isernia C, Pedone C, Benedetti E, Altmann E, Mutter M
Non coded C alpha, alpha-disubstituted amino acids. X-ray diffraction analysis of a dipeptide containing (S)-alpha-methylserine (348 visite)
Int J Pept Protein Res (ISSN: 0367-8377, 0367-8377print, 0367-8377linking), 1993 Jan; 41(1): 15-20.
Impact Factor: 1.255
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Di Blasio B, Pavone V, Nastri F, Isernia C, Saviano M, Pedone C, Cucinotta V, Impellizzeri G, Rizzarelli E, Vecchio G
Conformation for a β-cyclodextrin monosubstituted with a cyclic dipeptide (452 visite)
P Natl Acad Sci Usa (ISSN: 0027-8424, 1091-6490, 0027-8424print), 1992 Sep 1; 89(15): 7218-7221.
Impact Factor: 9.04
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46 Records (44 escludendo Abstract e Conferenze).
Impact factor totale: 198.043 (189.463 escludendo Abstract e Conferenze).
Impact factor a 5 anni totale: 182.518 (173.141 escludendo Abstract e Conferenze).
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