Synthesis of a diaminopropanoic acid-based nucleoamino acid and assembly of cationic nucleopeptides for biomedical applications (444 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2012 Dec; 43(6): 2537-2543.
Export to BibTeX Export to EndNote
Paper type: Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 3.914, 5-year impact factor: 3.742
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84872685673&partnerID=40&md5=27ef34cb2101eadd2213f775657b4c5f
Keywords: Dna, Nucleopeptide, Rna, Alpha Amino Acid, Diamino Acid, Diaminopropionic Acid, Dna Base, Lysine, N Beta 9 Fluorenylmethoxycarbonyl 2, 3 Diaminopropanoic Acid, N Beta 9 Fluorenylmethoxycarbonyl N Alpha (thymin 1 Ylacetyl) 2, 3 Propanoic Acid, Nucleoamino Acid, Nucleoprotein, Oligonucleotide, Unclassified Drug, Amino Acid Analysis, Amino Acid Sequence, Amino Acid Synthesis, Article, Biomedicine, Circular Dichroism, Conformational Transition, Electrospray Mass Spectrometry, Enzyme Degradation, Human, Human Cell, Nuclear Magnetic Resonance, Priority Journal, Protein Assembly, Protein Binding, Protein Dna Interaction, Protein Purification, Protein Rna Binding, Rna Structure, Solid Phase Synthesis, Beta-Alanine, Drug Stability, Models, Molecular, Molecular Structure, Peptide Nucleic Acids, Spectrophotometry, Ultraviolet,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini-CNR, Via Mezzocannone 16, 80134 Naples, Italy
Dipartimento Delle Scienze Biologiche, Universita di Napoli Federico II, 80134 Naples, Italy
References:
Abramova, T.V., Vlassov, V.V., Zarytova, V.F., Ivanova, E.M., Kuligina, E.A., Ryte, A.S., The effect of oligodeoxyribonucleotide terminal phosphate and ribose modification on the interactions of oligonucleotides with cells and intracellular stability (1991) Nucleosides Nucleotides, 10, pp. 639-64
Bell, N.M., Micklefield, J., Chemical modification of oligonucleotides for therapeutic, bioanalytical and other applications (2009) ChemBioChem, 10, pp. 2691-2703
Calabretta, A., Tedeschi, T., Di Cola, G., Corradini, R., Sforza, S., Marchelli, R., Arginine-based PNA microarrays for APOE genotyping (2009) Mol BioSyst, 5, pp. 1323-1330
D'alonzo, D., Guaragna, A., Palumbo, G., Exploring the role of chirality in nucleic acid recognition (2011) Chem Biodivers, 8, pp. 373-413
Dragulescu-Andrasi, A., Rapireddy, S., He, G., Bhattacharya, B., Hyldig-Nielsen, J.J., Zon, G., Ly, D.H., Cell-permeable peptide nucleic acid designed to bind to the 5-untranslated region of E-cadherin transcript induces potent and sequence-specific antisense effects (2006) Journal of the American Chemical Society, 128 (50), pp. 16104-16112. , DOI 10.1021/ja063383v
Katritzky, A.R., Narindoshvili, T., Chiral peptide nucleic acid monomers (PNAM) with modified backbones (2008) Org Biomol Chem, 6, pp. 3171-3176
Krzyzanowska, D., Lisowski, M., Kochman, M., UV-difference and CD spectroscopy studies on juvenile hormone binding to its carrier protein (1998) Journal of Peptide Research, 51 (2), pp. 96-102
Petraccone, L., Pagano, B., Esposito, V., Randazzo, A., Piccialli, G., Barone, G., Mattia, C.A., Giancola, C., Thermodynamics and kinetics of PNA-DNA quadruplex-forming chimeras (2005) Journal of the American Chemical Society, 127 (46), pp. 16215-16223. , DOI 10.1021/ja0545923
Rocchi, R., Borin, G., Marchiori, F., Moroder, L., Peggion, E., Scoffone, E., Crescenzi, V., Quadrifoglio, F., Interaction of S-protein with S-peptide and with synthetic S-peptide analogs (1972) A Spectroscopic and Calorimetric Investigation. Biochemistry, 11, pp. 50-57
Roviello, G.N., Moccia, M., Sapio, R., Valente, M., Bucci, E.M., Castiglione, M., Pedone, C., Musumeci, D., Synthesis, characterization and hybridization studies of new nucleo-gamma-peptides based on diaminobutyric acid (2006) Journal of Peptide Science, 12 (12), pp. 829-835. , DOI 10.1002/psc.819
Roviello, G.N., Musumeci, D., Moccia, M., Castiglione, M., Sapio, R., Valente, M., Bucci, E.M., Pedone, C., DabPNA: Design, synthesis, and DNA binding studies (2007) Nucleosides, Nucleotides and Nucleic Acids, 26 (10-12), pp. 1307-1310. , DOI 10.1080/15257770701530640, PII 788145344
Roviello, G.N., Benedetti, E., Pedone, C., Bucci, E.M., Nucleobasecontaining peptides: An overview of their characteristic features and applications (2010) Amino Acids, 39, pp. 45-57
Sforza, S., Galaverna, G., Dossena, A., Corradini, R., Marchelli, R., Role of chirality and optical purity in nucleic acid recognition by PNA and PNA analogs (2002) Chirality, 14 (7), pp. 591-598. , DOI 10.1002/chir.10087
Van Der Laan, A.C., Van Amsterdam, I., Tesser, G.I., Van Boom, J.H., Kuyl-Yeheskiely, E., Synthesis of chirally pure ornithine based PNA analogues (1998) Nucleosides and Nucleotides, 17 (1-3), pp. 219-231
Zatsepin, T.S., Romanova, E.A., Stetsenko, D.A., Gait, M.J., Oretskaya, T.S., Synthesis of 2-modified oligonucleotides containing aldehyde or ethylenediamine groups (2003) Nucleosides, Nucleotides and Nucleic Acids, 22 (5-8), pp. 1383-1385. , DOI 10.1081/NCN-120022971
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2012 Dec; 43(6): 2537-2543.
Export to BibTeX Export to EndNote
Paper type: Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 3.914, 5-year impact factor: 3.742
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84872685673&partnerID=40&md5=27ef34cb2101eadd2213f775657b4c5f
Keywords: Dna, Nucleopeptide, Rna, Alpha Amino Acid, Diamino Acid, Diaminopropionic Acid, Dna Base, Lysine, N Beta 9 Fluorenylmethoxycarbonyl 2, 3 Diaminopropanoic Acid, N Beta 9 Fluorenylmethoxycarbonyl N Alpha (thymin 1 Ylacetyl) 2, 3 Propanoic Acid, Nucleoamino Acid, Nucleoprotein, Oligonucleotide, Unclassified Drug, Amino Acid Analysis, Amino Acid Sequence, Amino Acid Synthesis, Article, Biomedicine, Circular Dichroism, Conformational Transition, Electrospray Mass Spectrometry, Enzyme Degradation, Human, Human Cell, Nuclear Magnetic Resonance, Priority Journal, Protein Assembly, Protein Binding, Protein Dna Interaction, Protein Purification, Protein Rna Binding, Rna Structure, Solid Phase Synthesis, Beta-Alanine, Drug Stability, Models, Molecular, Molecular Structure, Peptide Nucleic Acids, Spectrophotometry, Ultraviolet,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini-CNR, Via Mezzocannone 16, 80134 Naples, Italy
Dipartimento Delle Scienze Biologiche, Universita di Napoli Federico II, 80134 Naples, Italy
References:
Abramova, T.V., Vlassov, V.V., Zarytova, V.F., Ivanova, E.M., Kuligina, E.A., Ryte, A.S., The effect of oligodeoxyribonucleotide terminal phosphate and ribose modification on the interactions of oligonucleotides with cells and intracellular stability (1991) Nucleosides Nucleotides, 10, pp. 639-64
Bell, N.M., Micklefield, J., Chemical modification of oligonucleotides for therapeutic, bioanalytical and other applications (2009) ChemBioChem, 10, pp. 2691-2703
Calabretta, A., Tedeschi, T., Di Cola, G., Corradini, R., Sforza, S., Marchelli, R., Arginine-based PNA microarrays for APOE genotyping (2009) Mol BioSyst, 5, pp. 1323-1330
D'alonzo, D., Guaragna, A., Palumbo, G., Exploring the role of chirality in nucleic acid recognition (2011) Chem Biodivers, 8, pp. 373-413
Dragulescu-Andrasi, A., Rapireddy, S., He, G., Bhattacharya, B., Hyldig-Nielsen, J.J., Zon, G., Ly, D.H., Cell-permeable peptide nucleic acid designed to bind to the 5-untranslated region of E-cadherin transcript induces potent and sequence-specific antisense effects (2006) Journal of the American Chemical Society, 128 (50), pp. 16104-16112. , DOI 10.1021/ja063383v
Katritzky, A.R., Narindoshvili, T., Chiral peptide nucleic acid monomers (PNAM) with modified backbones (2008) Org Biomol Chem, 6, pp. 3171-3176
Krzyzanowska, D., Lisowski, M., Kochman, M., UV-difference and CD spectroscopy studies on juvenile hormone binding to its carrier protein (1998) Journal of Peptide Research, 51 (2), pp. 96-102
Petraccone, L., Pagano, B., Esposito, V., Randazzo, A., Piccialli, G., Barone, G., Mattia, C.A., Giancola, C., Thermodynamics and kinetics of PNA-DNA quadruplex-forming chimeras (2005) Journal of the American Chemical Society, 127 (46), pp. 16215-16223. , DOI 10.1021/ja0545923
Rocchi, R., Borin, G., Marchiori, F., Moroder, L., Peggion, E., Scoffone, E., Crescenzi, V., Quadrifoglio, F., Interaction of S-protein with S-peptide and with synthetic S-peptide analogs (1972) A Spectroscopic and Calorimetric Investigation. Biochemistry, 11, pp. 50-57
Roviello, G.N., Moccia, M., Sapio, R., Valente, M., Bucci, E.M., Castiglione, M., Pedone, C., Musumeci, D., Synthesis, characterization and hybridization studies of new nucleo-gamma-peptides based on diaminobutyric acid (2006) Journal of Peptide Science, 12 (12), pp. 829-835. , DOI 10.1002/psc.819
Roviello, G.N., Musumeci, D., Moccia, M., Castiglione, M., Sapio, R., Valente, M., Bucci, E.M., Pedone, C., DabPNA: Design, synthesis, and DNA binding studies (2007) Nucleosides, Nucleotides and Nucleic Acids, 26 (10-12), pp. 1307-1310. , DOI 10.1080/15257770701530640, PII 788145344
Roviello, G.N., Benedetti, E., Pedone, C., Bucci, E.M., Nucleobasecontaining peptides: An overview of their characteristic features and applications (2010) Amino Acids, 39, pp. 45-57
Sforza, S., Galaverna, G., Dossena, A., Corradini, R., Marchelli, R., Role of chirality and optical purity in nucleic acid recognition by PNA and PNA analogs (2002) Chirality, 14 (7), pp. 591-598. , DOI 10.1002/chir.10087
Van Der Laan, A.C., Van Amsterdam, I., Tesser, G.I., Van Boom, J.H., Kuyl-Yeheskiely, E., Synthesis of chirally pure ornithine based PNA analogues (1998) Nucleosides and Nucleotides, 17 (1-3), pp. 219-231
Zatsepin, T.S., Romanova, E.A., Stetsenko, D.A., Gait, M.J., Oretskaya, T.S., Synthesis of 2-modified oligonucleotides containing aldehyde or ethylenediamine groups (2003) Nucleosides, Nucleotides and Nucleic Acids, 22 (5-8), pp. 1383-1385. , DOI 10.1081/NCN-120022971
Synthesis of a diaminopropanoic acid-based nucleoamino acid and assembly of cationic nucleopeptides for biomedical applications
In this work, we report a synthetic approach to a Fmoc-protected nucleoamino acid, based on L-diaminopropanoic acid, carrying the DNA nucleobase on the alphaamino group by means of an amide bond, suitable for the solid-phase synthesis of novel nucleopeptides of potential interest in biomedicine. After ESI-MS and NMR characterization this building block was used for the assembly of a thymine-functionalized nucleopeptide, composed of nucleobase-containing L-diaminopropanoic acid moieties and underivatized L-lysine residues alternated in the backbone. Circular dichroism studies performed on the cationic nucleopeptide and adenine-containing DNA and RNA molecules suggested that the thymine-containing peptide is able to interact with both DNA and RNA. In particular, a significant conformational variation in the RNA structure was suggested by CD studies. Human serum stability assays were also conducted on the cationic nucleopeptide, which was found to be highly resistant to enzymatic degradation. © Springer-Verlag 2012.
In this work, we report a synthetic approach to a Fmoc-protected nucleoamino acid, based on L-diaminopropanoic acid, carrying the DNA nucleobase on the alphaamino group by means of an amide bond, suitable for the solid-phase synthesis of novel nucleopeptides of potential interest in biomedicine. After ESI-MS and NMR characterization this building block was used for the assembly of a thymine-functionalized nucleopeptide, composed of nucleobase-containing L-diaminopropanoic acid moieties and underivatized L-lysine residues alternated in the backbone. Circular dichroism studies performed on the cationic nucleopeptide and adenine-containing DNA and RNA molecules suggested that the thymine-containing peptide is able to interact with both DNA and RNA. In particular, a significant conformational variation in the RNA structure was suggested by CD studies. Human serum stability assays were also conducted on the cationic nucleopeptide, which was found to be highly resistant to enzymatic degradation. © Springer-Verlag 2012.
Synthesis of a diaminopropanoic acid-based nucleoamino acid and assembly of cationic nucleopeptides for biomedical applications
Synthesis of a diaminopropanoic acid-based nucleoamino acid and assembly of cationic nucleopeptides for biomedical applications
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Impact Factor: 0
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Roviello GN, Musumeci D
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Impact Factor: 3.108
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Roviello GN, Vicidomini C, Di Gaetano S, Capasso D, Musumeci D, Roviello V
* Solid phase synthesis and RNA-binding activity of an arginine-containing nucleopeptide (402 views)
Rsc Adv (ISSN: 2046-2069), 2016; 6(17): 14140-14148.
Impact Factor: 3.108
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Roviello GN, Musumeci D, Roviello V, Pirtskhalava M, Egoyan A, Mirtskhulava M
* Natural and artificial binders of polyriboadenylic acid and their effect on RNA structure (380 views)
Beilstein J Nanotech (ISSN: 2190-4286), 2015; 6(1): 1338-1347.
Impact Factor: 2.778
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Roviello GN, Musumeci D, D'Alessandro C, Pedone C
* Binding ability of a thymine-functionalized oligolysine towards nucleic acids (347 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 0968-0896linking), 2014 Feb 1; 22(3): 997-1002.
Impact Factor: 2.793
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Roviello GN, Musumeci D, D'Alessandro C, Pedone C
* Synthesis of a thymine-functionalized nucleoamino acid for the solid phase assembly of cationic nucleopeptides (486 views)
Amino Acids (ISSN: 1438-2199, 0939-4451, 1438-2199electronic), 2013 Oct; 45(4): 779-784.
Impact Factor: 3.653
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Roviello GN, Roviello G, Musumeci D, Bucci EM, Pedone C
* Dakin-West reaction on 1-thyminyl acetic acid for the synthesis of 1, 3-bis(1-thyminyl)-2-propanone, a heteroaromatic compound with nucleopeptide-binding properties (439 views)
Amino Acids (ISSN: 1438-2199, 0939-4451, 1438-2199electronic), 2012 Oct; 43(4): 1615-1623.
Impact Factor: 3.914
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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 (538 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2011 Oct; 41(4): 981-990.
Impact Factor: 3.248
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Roviello GN, Musumeci D, Bucci EM, Pedone C
* Synthesis and characterization of a novel ester-based nucleoamino acid for the assembly of aromatic nucleopeptides for biomedical applications (531 views)
Int J Pharm (ISSN: 0378-5173, 1873-3476), 2011 Sep 30; 415(1-2): 206-210.
Impact Factor: 3.35
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Roviello GN, Di Gaetano S, Capasso D, Franco S, Crescenzo C, Bucci EM, Pedone C
* RNA-binding and viral reverse transcriptase inhibitory activity of a novel cationic diamino acid-based peptide (610 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2011 Apr 14; 54(7): 2095-2101.
Impact Factor: 5.248
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Roviello GN, Musumeci D, Bucci EM, Pedone C
* Evidences for supramolecular organization of nucleopeptides: Synthesis, spectroscopic and biological studies of a novel dithymine l-serine tetrapeptide (578 views)
Mol Biosyst (ISSN: 1742-206x, 1742-2051, 1742-2051electronic), 2011 Apr; 7(4): 1073-1080.
Impact Factor: 3.534
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Roviello GN, Crescenzo C, Capasso D, Di Gaetano S, Franco S, Bucci EM, Pedone C
* Synthesis of a novel Fmoc-protected nucleoaminoacid for the solid phase assembly of 4-piperidyl glycine/L-arginine-containing nucleopeptides and preliminary RNA interaction studies (464 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 Sep; 39(3): 795-800.
Impact Factor: 4.106
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Roviello GN, Benedetti E, Pedone C, Bucci EM
* Nucleobase-containing peptides: An overview of their characteristic features and applications (753 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 Jun; 39(1): 45-57.
Impact Factor: 4.106
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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 (804 views)
Amino Acids (ISSN: 1438-2199, 0939-4451, 1438-2199electronic), 2010 May; 38(5): 1301-1309.
Impact Factor: 4.106
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Roviello GN, Di Gaetano S, Capasso D, Cesarani A, Bucci EM, Pedone C
* Synthesis, spectroscopic studies and biological activity of a novel nucleopeptide with Moloney murine leukemia virus reverse transcriptase inhibitory activity (443 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 May; 38(5): 1489-1496.
Impact Factor: 4.106
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Roviello GN, Musumeci D, Pedone C, Bucci EM
* Synthesis, Characterization And Hybridization Studies Of An Alternate Nucleo-Epsilon/Gamma-Peptide: Complexes Formation With Natural Nucleic Acids (494 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2010 Jan; 38(1): 103-111.
Impact Factor: 4.106
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Roviello GN, Musumeci D, Castiglione M, Bucci EM, Pedone C, Benedetti E
* Solid Phase Synthesis And Rna-Binding Studies Of A Serum-Resistant Nucleo-Epsilon-Peptide (435 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2009 Mar; 15(3): 155-160.
Impact Factor: 1.807
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Roviello GN, Musumeci D, Moccia M, Castiglione M, Sapio R, Valente M, Bucci EM, Perretta G, Pedone C
* Dabpna: Design, Synthesis And Nucleic Acids Binding Studies (430 views)
Nucleosides Nucleotides Nucleic Acids (ISSN: 1525-7770), 2007; 26(10-12): 1307-1310.
Impact Factor: 0.723
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Cucinotta V, Giuffrida A, Grasso G, Maccarrone G, Messina M, Vecchio G
* High selectivity in new chiral separations of dansyl amino acids by cyclodextrin derivatives in electrokinetic chromatography (290 views)
J Chromatogr A (ISSN: 0021-9673, 0021-9673linking), 2007; 1155(2): 172-179.
Impact Factor: 3.641
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Roviello GN, Moccia M, Sapio R, Valente M, Bucci EM, Castiglione M, Pedone C, Perretta G, Benedetti E, Musumeci D
* Synthesis, Characterization And Hybridization Studies Of New Nucleo-Gamma-Peptides Based On Diaminobutyric Acid (493 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2006 Dec; 12(12): 829-835.
Impact Factor: 1.801
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Dalla Bona A, Formaggio F, Peggion C, Kaptein B, Broxterman Quirinus B, Galdiero S, Galdiero M, Vitiello M, Benedetti E, Toniolo C
* Synthesis, conformation, and bioactivity of novel analogues of the antiviral lipopeptide halovir (501 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2006 Dec; 12(12): 748-757.
Impact Factor: 1.801
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Isernia C, Bucci E, Leone M, Zaccaro L, Di Lello P, Digilio G, Esposito S, Saviano M, Di Blasio B, Pedone C, Pedone PV, Fattorusso R
* NMR structure of the single QALGGH zinc finger domain from the Arabidopsis thaliana SUPERMAN protein (430 views)
Chembiochem (ISSN: 1439-4227, 1439-7633, 1439-7633electronic), 2003 Mar 3; 4(2-3): 171-180.
Impact Factor: 3.992
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Formaggio F, Bonchio M, Crisma M, Peggion C, Mezzato S, Polese A, Barazza A, Antonello S, Maran F, Broxterman QB, Kaptein B, Kamphuis J, Vitale RM, Saviano M, Benedetti E, Toniolo C
* Nitroxyl peptides as catalysts of enantioselective oxidations (498 views)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2002; 8(1): [d]84-93.
Impact Factor: 4.238
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29 Records (29 excluding Abstracts).
Total impact factor: 102.704 (102.704 excluding Abstracts).
Total 5 year impact factor: 100.565 (100.565 excluding Abstracts).
Total impact factor: 102.704 (102.704 excluding Abstracts).
Total 5 year impact factor: 100.565 (100.565 excluding Abstracts).
444 views. Last view on Thursday 09 March 2023, 21:57:14
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