Nitroxyl peptides as catalysts of enantioselective oxidations (316 visite)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2002; 8(1): [d]84-93.
Tipo di articolo: Journal Article,
Impact factor: 4.238, Impact factor a 5 anni: 5.608
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0037016790&partnerID=40&md5=eb49bc7b5dd6b6ec669b6959031ef518
Parole chiave: 1 Aminocyclohexanecarboxylic Acid, 1-Aminocyclohexanecarboxylic Acid, 2 Amino 2 Methylpropionic Acid, 6 Tetramethylpiperidine N Oxide 4 Amino 4 Carboxylic Acid, 6-Tetramethylpiperidine-N-Oxide-4-Amino-4-Carboxylic Acid, Acetophenone, Acetophenone Derivative, Amine Oxide, Amino Acid, C(alpha) Methyl Valine, C(alpha)-Methyl Valine, Cyclohexanecarboxylic Acid Derivative, Drug Derivative, Nitrogen Oxide, Nitroxyl, Oligopeptide, Phenethyl Alcohol, Article, Catalysis, Chemical Structure, Chemistry, Infrared Spectrophotometry, Infrared Spectroscopy, Nuclear Magnetic Resonance, Oxidation Reduction Reaction, Physical Chemistry, Protein Conformation, Spin Labeling, Stereoisomerism, Synthesis, X Ray Diffraction, Aminoisobutyric Acids, Cyclic N-Oxides, Models, Molecular, Molecular Structure, Biomolecular, Oxidation-Reduction, Phenylethyl Alcohol, Fourier Transform Infrared, X-Ray Diffraction, Asymmetric Catalysis, Conformation Analysis, Peptidomimetics, Hydrogen Bonds, Terminal Blocking Groups, 1 Phenylethanol, Alpha Amino Acid, Cyclic N Oxides, Carboxy Terminal Sequence, Diastereoisomer, Enantioselectivity, C (alpha) Methyl Valine, C (alpha) -Methyl Valine,
Affiliazioni:
*** IBB - CNR ***
Department of Organic Chemistry, University of Padova, CNR Centre CSB, Italy.
Department of Physical Chemistry, University of Padova, 35131 Padova, Italy
DSM Research, Organic Chemistry and Biotechnology Section, P. O. Box 18, 6160 MD Geleen, Netherlands
DSM Food Specialties, Nutritional Ingredients, P. O. Box 1, 2600 Delft, Netherlands
Department of Environmental Sciences, 2nd University of Naples, 81100 Caserta, Italy
Biocrystallography Research Centre, CNR Department of Chemistry, University of Naples Federico II, 80134 Naples, Italy
Riferimenti:
Venkatachalam, C.M., (1968) Biopolymers, 6, pp. 1425-143
Toniolo, C., (1980) Crit. Rev. Biochem., 9, pp. 1-44
Rose, G.D., Gierasch, L.M., Smith, J.A., (1985) Adv. Protein Chem., 37, pp. 1-109
Toniolo, C., Benedetti, E., (1991) Trends Biochem. Sci., 16, pp. 350-353
Karle, I.L., Balaram, P., (1990) Biochemistry, 29, pp. 6747-6756
Toniolo, C., Crisma, M., Formaggio, F., (1998) Biopolymers, 47, pp. 153-158
Toniolo, C., Valente, E., Formaggio, F., Crisma, M., Pilloni, G., Corvaja, C., Toffoletti, A., Flippen-Anderson, J.L., (1995) J. Pept. Sci., 1, pp. 45-57
Monaco, V., Formaggio, F., Crisma, M., Toniolo, C., Hanson, P., Millhauser, G., George, C., Flippen-Anderson, J.L., (1999) Bioorg. Med. Chem., 7, pp. 119-131
Toniolo, C., Formaggio, F., Crisma, M., Mazaleyrat, J.P., Wakselman, M., George, C., Deschamps, J.R., Palleschi, A., (1999) Chem. Eur. J., 5, pp. 2254-2264
Pispisa, B., Mazzuca, C., Palleschi, A., Stella, L., Venanzi, M., Formaggio, F., Polese, A., Toniolo, C., (2000) Biopolymers, 55, pp. 425-435
Valle, G., Crisma, M., Toniolo, C., Polinelli, S., Boesten, W.H.J., Schoemaker, H.E., Meijer, E.M., Kamphuis, J., (1991) Int. J. Pept. Protein Res., 37, pp. 521-527
Formaggio, F., Pantano, M., Valle, G., Crisma, M., Bonora, G.M., Mammi, S., Peggion, E., Kamphuis, J., (1993) Macromolecules, 26, pp. 1848-1852
Polese, A., Formaggio, F., Crisma, M., Valle, G., Toniolo, C., Bonora, G.M., Broxterman, Q.B., Kamphuis, J., (1996) Chem. Eur. J., 2, pp. 1104-1111
Toniolo, C., Polese, A., Formaggio, F., Crisma, M., Kamphuis, J., (1996) J. Am. Chem. Soc., 118, pp. 2744-2745
Kruizinga, W.H., Bolster, J., Kellogg, R.M., Kamphuis, J., Boesten, W.H.J., Meijer, E.M., Schoemaker, H.E., (1988) J. Org. Chem., 53, pp. 1826-1827
Sonke, T., Kaptein, B., Boesten, W.H.J., Broxterman, Q.B., Schoemaker, H.E., Kamphuis, J., Formaggio, F., Rutjes, F.P.J.T., (1999) Stereselective Biocatalysis, pp. 23-58. , (Ed.: R. N. Patel), Dekker, New York
Carpino, L.A., Mansour, E.S.M.E., Sadat-Aalaee, D., (1991) J. Org. Chem., 56, pp. 2611-2614
Marchetto, R., Schreier, S., Nakaie, C.R., (1993) J. Am. Chem. Soc., 115, pp. 11042-11043
Nakaie, C.R., Schreier, S., Paiva, A.C.M., (1983) Biochim. Biophys. Acta, 742, pp. 63-71
Dulog, L., Wang, W., (1992) Liebigs Ann. Chem., pp. 301-303
Carpino, L.A., (1993) J. Am. Chem. Soc., 115, pp. 4397-4398
Bonora, G.M., Mapelli, C., Toniolo, C., Wilkening, R.R., Stevens, E.S., (1984) Int. J. Biol. Macromol., 6, pp. 179-188
Palumbo, M., Da Rin, S., Bonora, G.M., Toniolo, C., (1976) Makromol. Chem., 177, pp. 1477-1492
Valle, G., Bonora, G.M., Toniolo, C., (1984) Can. J. Chem., 62, pp. 2661-2666
Chakrabarti, P., Dunitz, J.D., (1982) Helv. Chim. Acta, 65, pp. 1555-1562
Benedetti, E., (1982) Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins, 6, pp. 105-184. , (Ed.: B. Weinstein). Dekker, New York
Ashida, T., Tsunogae, Y., Tanaka, I., Yamane, T., (1987) Acta Crystallogr. Sect. B, 43, pp. 212-218
Crisma, M., Monaco, V., Formaggio, F., Toniolo, C., George, C., Flippen-Anderson, J.L., (1997) Lett. Pept. Sci., 4, pp. 213-218
(1970) Biochemistry, 9, pp. 3471-3479
Ramakrishnan, C., Prasad, N., (1971) Int. J. Protein Res., 3, pp. 209-231
Taylor, R., Kennard, O., Versichel, W., (1984) Acta Crystallogr. Sect. B, 40, pp. 280-288
Görbitz, C.H., (1989) Acta Crystallogr. Sect. B, 45, pp. 390-395
Cremer, D., Pople, J.A., (1975) J. Am. Chem. Soc., 97, pp. 1354-1358
Anelli, P.L., Biffi, C., Montanari, F., Quici, S., (1987) J. Org. Chem., 52, pp. 2559-2562
Bobbit, J.M., Flores, M.C.L., (1988) Heterocycles, 27, pp. 509-533
Rychnovski, S.D., Vaidyanathan, R., Beauchamp, T., Lin, R., Farmer, P.J., (1999) J. Org. Chem., 64, pp. 6745-6749
Ma, Z., Huang, Q., Bobbitt, J.M., (1993) J. Org. Chem., 58, pp. 4837-4843
Rychnovski, S.D., Mc Lernon, T.L., Rajapakse, H., (1996) J. Org. Chem., 61, pp. 1194-1195
Naik, N., Braslau, R., (1998) Tetrahedron, 54, pp. 667-696
Rychnovski, S.D., Beauchamp, T., Vaidyanathan, R., Kwan, T., (1998) J. Org. Chem., 63, pp. 6363-6374
Kashiwagi, Y., Yanagisawa, Y., Kurashima, F., Anzai, J., Osa, T., Bobbitt, J.M., (1996) Chem. Commun., pp. 2745-2746
Kashiwagi, Y., Kurashima, F., Kikuchi, C., Anzai, J., Osa, T., Bobbitt, J.M., (1999) Tetrahedron Lett., 40, pp. 6469-6472
Kashiwagi, Y., Uchiyama, K., Kurashima, F., Kikuchi, C., Anzai, J., (1999) Chem. Pharm. Bull., 47, pp. 1051-1052
Belgsir, E.M., Schäfer, H.J., (1999) Chem. Commun., pp. 435-436
Kuroboshi, M., Yoshihisa, H., Cortona, M.N., Kawakami, Y., Gao, Z., Tanaka, H., (2000) Tetrahedron Lett., 41, pp. 8131-8135
Tanaka, H., Kawakami, Y., Goto, K., Kuroboshi, M., (2001) Tetrahedron Lett., 42, pp. 445-448
Inoguchi, T., Matsumoto, S., Torii, S., (1991) J. Org. Chem., 56, pp. 2416-2421
Hunter, C.A., Lawson, K.R., Perkins, J., Urch, C.J., (2001) Perkin 2, pp. 651-669
Moitessier, N., Maigret, B., Chrétien, F., Chapleur, Y., (2000) Eur. J. Org. Chem., pp. 995-1005
Sheldrick, G.M., (1997) SHELXS 97, Program for the Solution of Crystal Structures, , University of Göttingen, Göttingen, Germany
Kagan, H.B., Fiaud, J.C., (1988) Top. Stereochem., 18, pp. 249-330
Némethy, G., Pottle, M.S., Scheraga, H.A., (1983) J. Phys. Chem., 87, pp. 1833-1887
(2000) InsightII and Discover User's Guides, , Molecular Simulations, San Diego, CA
Lifson, S., Hagler, A.T., Dauber, P.J., (1979) J. Am. Chem. Soc., 101, pp. 5111-5121
Hagler, A.T., Lifson, S., Dauber, P.J., (1979) J. Am. Chem. Soc., 101, pp. 5122-5130
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2002; 8(1): [d]84-93.
Tipo di articolo: Journal Article,
Impact factor: 4.238, Impact factor a 5 anni: 5.608
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0037016790&partnerID=40&md5=eb49bc7b5dd6b6ec669b6959031ef518
Parole chiave: 1 Aminocyclohexanecarboxylic Acid, 1-Aminocyclohexanecarboxylic Acid, 2 Amino 2 Methylpropionic Acid, 6 Tetramethylpiperidine N Oxide 4 Amino 4 Carboxylic Acid, 6-Tetramethylpiperidine-N-Oxide-4-Amino-4-Carboxylic Acid, Acetophenone, Acetophenone Derivative, Amine Oxide, Amino Acid, C(alpha) Methyl Valine, C(alpha)-Methyl Valine, Cyclohexanecarboxylic Acid Derivative, Drug Derivative, Nitrogen Oxide, Nitroxyl, Oligopeptide, Phenethyl Alcohol, Article, Catalysis, Chemical Structure, Chemistry, Infrared Spectrophotometry, Infrared Spectroscopy, Nuclear Magnetic Resonance, Oxidation Reduction Reaction, Physical Chemistry, Protein Conformation, Spin Labeling, Stereoisomerism, Synthesis, X Ray Diffraction, Aminoisobutyric Acids, Cyclic N-Oxides, Models, Molecular, Molecular Structure, Biomolecular, Oxidation-Reduction, Phenylethyl Alcohol, Fourier Transform Infrared, X-Ray Diffraction, Asymmetric Catalysis, Conformation Analysis, Peptidomimetics, Hydrogen Bonds, Terminal Blocking Groups, 1 Phenylethanol, Alpha Amino Acid, Cyclic N Oxides, Carboxy Terminal Sequence, Diastereoisomer, Enantioselectivity, C (alpha) Methyl Valine, C (alpha) -Methyl Valine,
Affiliazioni:
*** IBB - CNR ***
Department of Organic Chemistry, University of Padova, CNR Centre CSB, Italy.
Department of Physical Chemistry, University of Padova, 35131 Padova, Italy
DSM Research, Organic Chemistry and Biotechnology Section, P. O. Box 18, 6160 MD Geleen, Netherlands
DSM Food Specialties, Nutritional Ingredients, P. O. Box 1, 2600 Delft, Netherlands
Department of Environmental Sciences, 2nd University of Naples, 81100 Caserta, Italy
Biocrystallography Research Centre, CNR Department of Chemistry, University of Naples Federico II, 80134 Naples, Italy
Riferimenti:
Venkatachalam, C.M., (1968) Biopolymers, 6, pp. 1425-143
Toniolo, C., (1980) Crit. Rev. Biochem., 9, pp. 1-44
Rose, G.D., Gierasch, L.M., Smith, J.A., (1985) Adv. Protein Chem., 37, pp. 1-109
Toniolo, C., Benedetti, E., (1991) Trends Biochem. Sci., 16, pp. 350-353
Karle, I.L., Balaram, P., (1990) Biochemistry, 29, pp. 6747-6756
Toniolo, C., Crisma, M., Formaggio, F., (1998) Biopolymers, 47, pp. 153-158
Toniolo, C., Valente, E., Formaggio, F., Crisma, M., Pilloni, G., Corvaja, C., Toffoletti, A., Flippen-Anderson, J.L., (1995) J. Pept. Sci., 1, pp. 45-57
Monaco, V., Formaggio, F., Crisma, M., Toniolo, C., Hanson, P., Millhauser, G., George, C., Flippen-Anderson, J.L., (1999) Bioorg. Med. Chem., 7, pp. 119-131
Toniolo, C., Formaggio, F., Crisma, M., Mazaleyrat, J.P., Wakselman, M., George, C., Deschamps, J.R., Palleschi, A., (1999) Chem. Eur. J., 5, pp. 2254-2264
Pispisa, B., Mazzuca, C., Palleschi, A., Stella, L., Venanzi, M., Formaggio, F., Polese, A., Toniolo, C., (2000) Biopolymers, 55, pp. 425-435
Valle, G., Crisma, M., Toniolo, C., Polinelli, S., Boesten, W.H.J., Schoemaker, H.E., Meijer, E.M., Kamphuis, J., (1991) Int. J. Pept. Protein Res., 37, pp. 521-527
Formaggio, F., Pantano, M., Valle, G., Crisma, M., Bonora, G.M., Mammi, S., Peggion, E., Kamphuis, J., (1993) Macromolecules, 26, pp. 1848-1852
Polese, A., Formaggio, F., Crisma, M., Valle, G., Toniolo, C., Bonora, G.M., Broxterman, Q.B., Kamphuis, J., (1996) Chem. Eur. J., 2, pp. 1104-1111
Toniolo, C., Polese, A., Formaggio, F., Crisma, M., Kamphuis, J., (1996) J. Am. Chem. Soc., 118, pp. 2744-2745
Kruizinga, W.H., Bolster, J., Kellogg, R.M., Kamphuis, J., Boesten, W.H.J., Meijer, E.M., Schoemaker, H.E., (1988) J. Org. Chem., 53, pp. 1826-1827
Sonke, T., Kaptein, B., Boesten, W.H.J., Broxterman, Q.B., Schoemaker, H.E., Kamphuis, J., Formaggio, F., Rutjes, F.P.J.T., (1999) Stereselective Biocatalysis, pp. 23-58. , (Ed.: R. N. Patel), Dekker, New York
Carpino, L.A., Mansour, E.S.M.E., Sadat-Aalaee, D., (1991) J. Org. Chem., 56, pp. 2611-2614
Marchetto, R., Schreier, S., Nakaie, C.R., (1993) J. Am. Chem. Soc., 115, pp. 11042-11043
Nakaie, C.R., Schreier, S., Paiva, A.C.M., (1983) Biochim. Biophys. Acta, 742, pp. 63-71
Dulog, L., Wang, W., (1992) Liebigs Ann. Chem., pp. 301-303
Carpino, L.A., (1993) J. Am. Chem. Soc., 115, pp. 4397-4398
Bonora, G.M., Mapelli, C., Toniolo, C., Wilkening, R.R., Stevens, E.S., (1984) Int. J. Biol. Macromol., 6, pp. 179-188
Palumbo, M., Da Rin, S., Bonora, G.M., Toniolo, C., (1976) Makromol. Chem., 177, pp. 1477-1492
Valle, G., Bonora, G.M., Toniolo, C., (1984) Can. J. Chem., 62, pp. 2661-2666
Chakrabarti, P., Dunitz, J.D., (1982) Helv. Chim. Acta, 65, pp. 1555-1562
Benedetti, E., (1982) Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins, 6, pp. 105-184. , (Ed.: B. Weinstein). Dekker, New York
Ashida, T., Tsunogae, Y., Tanaka, I., Yamane, T., (1987) Acta Crystallogr. Sect. B, 43, pp. 212-218
Crisma, M., Monaco, V., Formaggio, F., Toniolo, C., George, C., Flippen-Anderson, J.L., (1997) Lett. Pept. Sci., 4, pp. 213-218
(1970) Biochemistry, 9, pp. 3471-3479
Ramakrishnan, C., Prasad, N., (1971) Int. J. Protein Res., 3, pp. 209-231
Taylor, R., Kennard, O., Versichel, W., (1984) Acta Crystallogr. Sect. B, 40, pp. 280-288
Görbitz, C.H., (1989) Acta Crystallogr. Sect. B, 45, pp. 390-395
Cremer, D., Pople, J.A., (1975) J. Am. Chem. Soc., 97, pp. 1354-1358
Anelli, P.L., Biffi, C., Montanari, F., Quici, S., (1987) J. Org. Chem., 52, pp. 2559-2562
Bobbit, J.M., Flores, M.C.L., (1988) Heterocycles, 27, pp. 509-533
Rychnovski, S.D., Vaidyanathan, R., Beauchamp, T., Lin, R., Farmer, P.J., (1999) J. Org. Chem., 64, pp. 6745-6749
Ma, Z., Huang, Q., Bobbitt, J.M., (1993) J. Org. Chem., 58, pp. 4837-4843
Rychnovski, S.D., Mc Lernon, T.L., Rajapakse, H., (1996) J. Org. Chem., 61, pp. 1194-1195
Naik, N., Braslau, R., (1998) Tetrahedron, 54, pp. 667-696
Rychnovski, S.D., Beauchamp, T., Vaidyanathan, R., Kwan, T., (1998) J. Org. Chem., 63, pp. 6363-6374
Kashiwagi, Y., Yanagisawa, Y., Kurashima, F., Anzai, J., Osa, T., Bobbitt, J.M., (1996) Chem. Commun., pp. 2745-2746
Kashiwagi, Y., Kurashima, F., Kikuchi, C., Anzai, J., Osa, T., Bobbitt, J.M., (1999) Tetrahedron Lett., 40, pp. 6469-6472
Kashiwagi, Y., Uchiyama, K., Kurashima, F., Kikuchi, C., Anzai, J., (1999) Chem. Pharm. Bull., 47, pp. 1051-1052
Belgsir, E.M., Schäfer, H.J., (1999) Chem. Commun., pp. 435-436
Kuroboshi, M., Yoshihisa, H., Cortona, M.N., Kawakami, Y., Gao, Z., Tanaka, H., (2000) Tetrahedron Lett., 41, pp. 8131-8135
Tanaka, H., Kawakami, Y., Goto, K., Kuroboshi, M., (2001) Tetrahedron Lett., 42, pp. 445-448
Inoguchi, T., Matsumoto, S., Torii, S., (1991) J. Org. Chem., 56, pp. 2416-2421
Hunter, C.A., Lawson, K.R., Perkins, J., Urch, C.J., (2001) Perkin 2, pp. 651-669
Moitessier, N., Maigret, B., Chrétien, F., Chapleur, Y., (2000) Eur. J. Org. Chem., pp. 995-1005
Sheldrick, G.M., (1997) SHELXS 97, Program for the Solution of Crystal Structures, , University of Göttingen, Göttingen, Germany
Kagan, H.B., Fiaud, J.C., (1988) Top. Stereochem., 18, pp. 249-330
Némethy, G., Pottle, M.S., Scheraga, H.A., (1983) J. Phys. Chem., 87, pp. 1833-1887
(2000) InsightII and Discover User's Guides, , Molecular Simulations, San Diego, CA
Lifson, S., Hagler, A.T., Dauber, P.J., (1979) J. Am. Chem. Soc., 101, pp. 5111-5121
Hagler, A.T., Lifson, S., Dauber, P.J., (1979) J. Am. Chem. Soc., 101, pp. 5122-5130
The achiral, nitroxyl-containing alpha-amino acid TOAC (TOAC = 2,2,6,6-tetramethylpiperidine-1-oxyl-4-amino-4-carboxylic acid), in combination with the chiral alpha-amino acid C(alpha)-methyl valine [(alphaMe)Val], was used to prepare short peptides (from di- to hexa-) that induced the enantioselective oxidation of racemic 1-phenylethanol to acetophenone. The best catalyst was an N(alpha)-acylated dipeptide alkylamide with the -TOAC-(alphaMe)Val- sequence folded in a stable, intramolecularly hydrogen-bonded beta-turn conformation with large, lipophilic (hydrophobic) N- and C-terminal blocking groups. We rationalized our findings by proposing models for the diastereomeric intermediates between (R)-[and (S)]-1-phenylethanol and the catalyst Fmoc-TOAC-L-(alphaMe)Val-NHiPr, based on the X-ray diffraction structure of the latter.
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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 (275 visite)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2001; 7(1): 15-26.
Impact Factor: 1.451
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1 Records (1 escludendo Abstract e Conferenze).
Impact factor totale: 1.451 (1.451 escludendo Abstract e Conferenze).
Impact factor a 5 anni totale: 1.715 (1.715 escludendo Abstract e Conferenze).
Impact factor totale: 1.451 (1.451 escludendo Abstract e Conferenze).
Impact factor a 5 anni totale: 1.715 (1.715 escludendo Abstract e Conferenze).
Esporta in BibTeX Esporta in EndNote
Ultima modifica di Marco Comerci in data Wednesday 26 March 2014, 9:29:57
316 visite. Ultima visita in data Friday 26 June 2020, 17:13:13
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