Nitroxyl peptides as catalysts of enantioselective oxidations
CNR Ibb | back to homepage
▲NavBar
Ricerca avanzata▼
Contiene: [X]      Estesa     Autori: [X]  Tipo di lavoro: [X]   Data iniziale: Data finale: [X]      Sede: Affiliazione IBB     
    
[Pulisci modulo]


Nitroxyl peptides as catalysts of enantioselective oxidations (190 visite)

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

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.
Nessun risultato.
Nessun risultato.

Ricerca avanzata▼
Contiene: [X]      Estesa     Autori: [X]  Tipo di lavoro: [X]   Data iniziale: Data finale: [X]      Sede: Affiliazione IBB     
    
[Pulisci modulo]
Vai a fine pagina   Versione per copia e incolla facile   Esporta tutto in BibTeX   Esporta tutto in EndNote


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 (172 visite)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2001; 7(1): 15-26.
Impact Factor: 1.451
Dettagli    Esporta in BibTeX    Esporta in EndNote



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).







    Esporta in BibTeX    Esporta in EndNote