Nitroxyl peptides as catalysts of enantioselective oxidations
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Nitroxyl peptides as catalysts of enantioselective oxidations (186 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


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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 (169 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).







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