Synthetic strategy for side chain mono-N-alkylation of Fmoc-amino acids promoted by molecular sieves (502 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2011 Oct; 41(4): 981-990.
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Paper type: Journal Article,
Impact factor: 3.248, 5-year impact factor: 3.138
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-83255189527&partnerID=40&md5=bdef1a057f6cb9eeca5ece371ebd2f21
Keywords: Molecular Sieves, N-Alkylated Amino Acids, N-Alkylation, Peptidomimetics, Alkylate Amino Acid, Halogenoalkane, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta 1 Heptenyl N, Beta 2 Nitrobenzensulfonyl Levo 2, 3 Diaminopropionic Acid, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta 2 Phenylethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta 3 Phenylpropyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta Benzyl N, Beta Methylthrityl Levo 2, Beta Tert Butoxycarbonyl Levo 2, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta Diphenylmethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta Ethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta Methyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta Naphthylmethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta Propyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta Tert Butylacetyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Delta Benzyl N, Delta 2 Nitrobenzensulfonyl Levo Ornithine, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon 2 Phenylethyl N, Epsilon 2 Nitrobenzensulfonyl Levo Lysine, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon 3 Phenylethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon Benzyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon Diphenylmethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon Ethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon Methyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon Naphthylmethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon Propyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon Tert Butylacetyl N, N Alpha [9 Fluorenylmethoxycarbonyl] N Beta Benzyl N, 4 Diemthyl 2, 6 Dioxocycloex 1 Ylidene) 3 Methylbutyl Levo 2, Unclassified Drug, Amino Acid Sequence, Article, Chemical Structure, Mass Spectrometry, Nuclear Magnetic Resonance Spectroscopy, Particle Size, Priority Journal, Protein Synthesis,
Affiliations:
*** IBB - CNR ***
Institute of Biostructures and Bioimages, National Research Council, 80138 Naples, Italy
References:
Andersen, T.F., Stromgaard, K., Synthesis of polyamines and polyamine toxins (2004) An improved alkylation procedure. Tetrahedron Lett, 45, pp. 7929-793
Biron, E., Kessler, H., Convenient synthesis of N-methylamino acids compatible with Fmoc solid-phase peptide synthesis (2005) J Org Chem, 70, pp. 5183-5189
Biron, E., Chatterjee, J., Kessler, H., N-methylation of peptides on solid support (2006) J Pept Sci, 12, pp. 213-219
Cho, J.H., Kim, B.M., LiOH-mediated N-monoalkylation of a-amino acid esters and a dipeptide ester using activated alkyl bromides (2002) Tetrahedron Lett, 43, pp. 1273-1276
Dankwardt, S.M., Smith, D.B., Porco, J.A., Nguyen, C.H., Solid phase synthesis of N-alkyl sulfonamides (1997) Synlett, 25, pp. 854-856
De Gioia, M.L., Leggio, A., Liguori, A., N-methylation of peptides on selected positions during the elongation of the peptide chain in solution phase (2005) J Org Chem, 70, pp. 3892-3897
De Luca, S., Della Moglie, R., De Capua, A., Morelli, G., New synthetic strategy for o-NBS protected amino acids and their use in synthesis of mono-benzylated peptides (2005) Tetrahedron Lett, 46, pp. 6637-6640
Demmer, O., Dijkgraaf, I., Schottelius, M., Wester, H.J., Kessler, H., Introduction of functional groups into peptides via N-alkylation (2008) Org Lett, 10, pp. 2015-2018
Fukuyama, T., Cheung, M., Jow, C.K., Hidai, Y., Kan, T., 2,4- Dinitrobenzenesulfonamides: A simple and practical method for the preparation of a variety of secondary amines and diamines (1997) Tetrahedron Lett, 38, pp. 583-584
Gante, J., Peptidomimetics-tailored enzyme inhibitors (1994) Angew Chem Int Ed Eng, 33, pp. 1699-1720
Gazal, S., Gellerman, G., Gilon, C., Novel Gly building units for backbone cyclization: Synthesis and incorporation into model peptides (2003) Peptides, 24, pp. 1847-1852
Greene, T.W., Wuts, P.G.M., (2007) Protective Groups in Organic Synthesis, , 4th edn. Wiley, New York
Hahn, F., Schepers, U., Versatile procedure for asymmetric and orthogonal protection of symmetric polyamines and its advantages for solid phase synthesis (2008) J Comb Chem, 10, pp. 267-273
Hanessian, S., McNaughton-Smith, G., Lombart, H.G., Lubell, W.D., Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics (1997) Tetrahedron, 53, pp. 12789-12854
Hasegawa, M., Ono, F., Kanemasa, S., Molecular sieves 4A work to mediate the catalytic metal enolization of nucleophile precursors: Application to catalyzed enantioselective Michael addition reactions (2008) Tetrahedron Lett, 49, pp. 5220-5223
Huang, Z.P., Su, X.Y., Du, J.T., Zhao, Y.F., Li, Y.M., Facile synthesis of Ne-(benzyl, methyl)-lysine as a building block for site-specifically lysine monomethylated peptides (2006) Tetrahedron Lett, 47, pp. 5997-5999
Isidro-Llobet, A., Alverez, M., Albericio, F., Amino acidprotecting groups (2009) Chem Rev, 109, pp. 2455-2504
Kaiser, E., Colescott, R.L., Bossinger, C.D., Cook, P.I., Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides (1970) Anal Biochem, 34, pp. 595-598
Miller, S.C., Scanlan, T.S., ONBS-SPPS: A new method for solidphase peptide synthesis (1998) J Am Chem Soc, 120, pp. 2690-2691
Olsen, C.A., Franzyk, H., Jaroszewski, J.W., N-alkylation and indirect formation of amino functionalities in solid-phase synthesis (2005) Synthesis, 16, pp. 2631-2653
Reichwein, J.F., Liskamp, R.M.J., Site-specific N-alkylation of peptides on the solid phase (1998) Tetrahedron Lett, 39, pp. 1243-1246
Rew, Y., Goodman, M., Solid-phase synthesis of amine-bridged cyclic enkephalin analogues via on-resin cyclization utilizing the Fukuyama-Mitsunobu reaction (2002) J Org Chem, 67, pp. 8820-8826
Sasaki, Y., Coy, D.H., Solid phase synthesis of peptides containing the CH2NH peptide bond isostere (1987) Peptides, 8, pp. 119-121
Stodulski, M., Mlynarski, J., Synthesis of N-alkyl-N-methyl amino acids. Scope and limitations of base-induced N-alkylation of Cbz-amino acids (2008) Tetrahedron Asymmetr, 19, pp. 970-975
Toshiyuki, K., Fukuyama, T., Ns strategies: A highly versatile synthetic method for amines (2004) Chem Commun, pp. 353-359
Yang, L., Chiu, K., Solid phase synthesis of Fmoc N-methyl amino acids: Application of the Fukuyama amine synthesis (1997) Tetrahedron Lett, 38, pp. 7307-7310
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2011 Oct; 41(4): 981-990.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 3.248, 5-year impact factor: 3.138
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-83255189527&partnerID=40&md5=bdef1a057f6cb9eeca5ece371ebd2f21
Keywords: Molecular Sieves, N-Alkylated Amino Acids, N-Alkylation, Peptidomimetics, Alkylate Amino Acid, Halogenoalkane, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta 1 Heptenyl N, Beta 2 Nitrobenzensulfonyl Levo 2, 3 Diaminopropionic Acid, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta 2 Phenylethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta 3 Phenylpropyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta Benzyl N, Beta Methylthrityl Levo 2, Beta Tert Butoxycarbonyl Levo 2, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta Diphenylmethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta Ethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta Methyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta Naphthylmethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta Propyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Beta Tert Butylacetyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Delta Benzyl N, Delta 2 Nitrobenzensulfonyl Levo Ornithine, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon 2 Phenylethyl N, Epsilon 2 Nitrobenzensulfonyl Levo Lysine, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon 3 Phenylethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon Benzyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon Diphenylmethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon Ethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon Methyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon Naphthylmethyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon Propyl N, N Alpha (9 Fluorenylmethoxycarbonyl) N Epsilon Tert Butylacetyl N, N Alpha [9 Fluorenylmethoxycarbonyl] N Beta Benzyl N, 4 Diemthyl 2, 6 Dioxocycloex 1 Ylidene) 3 Methylbutyl Levo 2, Unclassified Drug, Amino Acid Sequence, Article, Chemical Structure, Mass Spectrometry, Nuclear Magnetic Resonance Spectroscopy, Particle Size, Priority Journal, Protein Synthesis,
Affiliations:
*** IBB - CNR ***
Institute of Biostructures and Bioimages, National Research Council, 80138 Naples, Italy
References:
Andersen, T.F., Stromgaard, K., Synthesis of polyamines and polyamine toxins (2004) An improved alkylation procedure. Tetrahedron Lett, 45, pp. 7929-793
Biron, E., Kessler, H., Convenient synthesis of N-methylamino acids compatible with Fmoc solid-phase peptide synthesis (2005) J Org Chem, 70, pp. 5183-5189
Biron, E., Chatterjee, J., Kessler, H., N-methylation of peptides on solid support (2006) J Pept Sci, 12, pp. 213-219
Cho, J.H., Kim, B.M., LiOH-mediated N-monoalkylation of a-amino acid esters and a dipeptide ester using activated alkyl bromides (2002) Tetrahedron Lett, 43, pp. 1273-1276
Dankwardt, S.M., Smith, D.B., Porco, J.A., Nguyen, C.H., Solid phase synthesis of N-alkyl sulfonamides (1997) Synlett, 25, pp. 854-856
De Gioia, M.L., Leggio, A., Liguori, A., N-methylation of peptides on selected positions during the elongation of the peptide chain in solution phase (2005) J Org Chem, 70, pp. 3892-3897
De Luca, S., Della Moglie, R., De Capua, A., Morelli, G., New synthetic strategy for o-NBS protected amino acids and their use in synthesis of mono-benzylated peptides (2005) Tetrahedron Lett, 46, pp. 6637-6640
Demmer, O., Dijkgraaf, I., Schottelius, M., Wester, H.J., Kessler, H., Introduction of functional groups into peptides via N-alkylation (2008) Org Lett, 10, pp. 2015-2018
Fukuyama, T., Cheung, M., Jow, C.K., Hidai, Y., Kan, T., 2,4- Dinitrobenzenesulfonamides: A simple and practical method for the preparation of a variety of secondary amines and diamines (1997) Tetrahedron Lett, 38, pp. 583-584
Gante, J., Peptidomimetics-tailored enzyme inhibitors (1994) Angew Chem Int Ed Eng, 33, pp. 1699-1720
Gazal, S., Gellerman, G., Gilon, C., Novel Gly building units for backbone cyclization: Synthesis and incorporation into model peptides (2003) Peptides, 24, pp. 1847-1852
Greene, T.W., Wuts, P.G.M., (2007) Protective Groups in Organic Synthesis, , 4th edn. Wiley, New York
Hahn, F., Schepers, U., Versatile procedure for asymmetric and orthogonal protection of symmetric polyamines and its advantages for solid phase synthesis (2008) J Comb Chem, 10, pp. 267-273
Hanessian, S., McNaughton-Smith, G., Lombart, H.G., Lubell, W.D., Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics (1997) Tetrahedron, 53, pp. 12789-12854
Hasegawa, M., Ono, F., Kanemasa, S., Molecular sieves 4A work to mediate the catalytic metal enolization of nucleophile precursors: Application to catalyzed enantioselective Michael addition reactions (2008) Tetrahedron Lett, 49, pp. 5220-5223
Huang, Z.P., Su, X.Y., Du, J.T., Zhao, Y.F., Li, Y.M., Facile synthesis of Ne-(benzyl, methyl)-lysine as a building block for site-specifically lysine monomethylated peptides (2006) Tetrahedron Lett, 47, pp. 5997-5999
Isidro-Llobet, A., Alverez, M., Albericio, F., Amino acidprotecting groups (2009) Chem Rev, 109, pp. 2455-2504
Kaiser, E., Colescott, R.L., Bossinger, C.D., Cook, P.I., Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides (1970) Anal Biochem, 34, pp. 595-598
Miller, S.C., Scanlan, T.S., ONBS-SPPS: A new method for solidphase peptide synthesis (1998) J Am Chem Soc, 120, pp. 2690-2691
Olsen, C.A., Franzyk, H., Jaroszewski, J.W., N-alkylation and indirect formation of amino functionalities in solid-phase synthesis (2005) Synthesis, 16, pp. 2631-2653
Reichwein, J.F., Liskamp, R.M.J., Site-specific N-alkylation of peptides on the solid phase (1998) Tetrahedron Lett, 39, pp. 1243-1246
Rew, Y., Goodman, M., Solid-phase synthesis of amine-bridged cyclic enkephalin analogues via on-resin cyclization utilizing the Fukuyama-Mitsunobu reaction (2002) J Org Chem, 67, pp. 8820-8826
Sasaki, Y., Coy, D.H., Solid phase synthesis of peptides containing the CH2NH peptide bond isostere (1987) Peptides, 8, pp. 119-121
Stodulski, M., Mlynarski, J., Synthesis of N-alkyl-N-methyl amino acids. Scope and limitations of base-induced N-alkylation of Cbz-amino acids (2008) Tetrahedron Asymmetr, 19, pp. 970-975
Toshiyuki, K., Fukuyama, T., Ns strategies: A highly versatile synthetic method for amines (2004) Chem Commun, pp. 353-359
Yang, L., Chiu, K., Solid phase synthesis of Fmoc N-methyl amino acids: Application of the Fukuyama amine synthesis (1997) Tetrahedron Lett, 38, pp. 7307-7310
Synthetic strategy for side chain mono-N-alkylation of Fmoc-amino acids promoted by molecular sieves
A new synthetic strategy to alkylate amino groups under mild conditions has been developed. It utilizes only 4 angstrom molecular sieves as base in order to promote the N-alkylation reaction, in presence of the appropriate alkyl halide. The methodology was validated by the simple and efficient side-chain N-alkylation of o-Ns-protected Fmoc-amino acid. One of them was introduced as building block into a peptide sequence, thus allowing the preparation of site-specific alkylated peptide molecules.
A new synthetic strategy to alkylate amino groups under mild conditions has been developed. It utilizes only 4 angstrom molecular sieves as base in order to promote the N-alkylation reaction, in presence of the appropriate alkyl halide. The methodology was validated by the simple and efficient side-chain N-alkylation of o-Ns-protected Fmoc-amino acid. One of them was introduced as building block into a peptide sequence, thus allowing the preparation of site-specific alkylated peptide molecules.
Synthetic strategy for side chain mono-N-alkylation of Fmoc-amino acids promoted by molecular sieves
Synthetic strategy for side chain mono-N-alkylation of Fmoc-amino acids promoted by molecular sieves
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Sinopoli A, Giuffrida A, Tomasello MF, Giuffrida ML, Leone M, Attanasio F, Caraci F, De Bona P, Naletova I, Saviano M, Copani A, Pappalardo G, Rizzarelli E
* Ac-LPFFD-Th: A Trehalose-Conjugated Peptidomimetic as a Strong Suppressor of Amyloid-beta Oligomer Formation and Cytotoxicity (453 views)
Chembiochem (ISSN: 1439-4227, 1439-7633, 1439-4227linking), 2016 Aug 17; 17(16): 1541-1549.
Impact Factor: 2.847
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Calce E, De Luca S
* Microwave heating in peptide side chain modification via cysteine alkylation (332 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2016 Jun 28; 48: 2267-2271.
Impact Factor: 3.173
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Celentano V, Diana D, Di Salvo C, De Rosa L, Romanelli A, Fattorusso R, D'Andrea LD
* 1, 2, 3-Triazole Bridge as Conformational Constrain in beta-Hairpin Peptides: Analysis of Hydrogen-Bonded Positions (442 views)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2016 Apr 11; 22(16): 5534-5537.
Impact Factor: 5.317
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Calce E, Leone M, Mercurio FA, Monfregola L, De Luca S
* Solid-Phase S-Alkylation Promoted by Molecular Sieves (270 views)
Org Lett (ISSN: 1523-7060, 1523-7052, 1523-7052electronic), 2015 Nov 20; 17(22): 5646-5649.
Impact Factor: 6.732
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Comegna D, de Paola I, Saviano M, Del Gatto A, Zaccaro L
* Straightforward entry to s-glycosylated fmoc-amino acids and their application to solid phase synthesis of glycopeptides and glycopeptidomimetics (490 views)
Org Lett (ISSN: 1523-7060, 1523-7052, 1523-7052electronic), 2015; 17(3): 640-643.
Impact Factor: 6.732
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Scognamiglio PL, Morelli G, Marasco D
* Synthetic and structural routes for the rational conversion of peptides into small molecules (472 views)
Methods Mol Biol (ISSN: 1064-3745, 1940-6029electronic, 1064-3745linking), 2015; 1268: 159-193.
Impact Factor: 3.221
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Calce E, Leone M, Monfregola L, De Luca S
* Lipidated Peptides Via Post-Synthetic Thioalkylation Promoted By Molecular Sieves (479 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2014; 46(8): 1899-1905.
Impact Factor: 3.293
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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 (468 views)
Org Lett (ISSN: 1523-7060, 1523-7052, 1523-7052electronic), 2012 Apr 6; 14(7): 1664-1667.
Impact Factor: 6.142
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Cirillo G, Colangelo AM, Bianco MR, Cavaliere C, Zaccaro L, Sarmientos P, Alberghina L, Papa M
* BB14, a Nerve Growth Factor (NGF)-like peptide shown to be effective in reducing reactive astrogliosis and restoring synaptic homeostasis in a rat model of peripheral nerve injury (402 views)
Biotechnology Advances (ISSN: 0734-9750), 2012 Jan; 30(1): 223-232.
Impact Factor: 9.599
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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 (489 views)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2002; 8(1): [d]84-93.
Impact Factor: 4.238
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19 Records (19 excluding Abstracts).
Total impact factor: 92.857 (92.857 excluding Abstracts).
Total 5 year impact factor: 77.576 (77.576 excluding Abstracts).
Total impact factor: 92.857 (92.857 excluding Abstracts).
Total 5 year impact factor: 77.576 (77.576 excluding Abstracts).
502 views. Last view on Tuesday 14 March 2023, 15:51:33
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