Nitroxyl peptides as catalysts of enantioselective oxidations (Articolo in rivista)

Type

• Prodotto della ricerca (Classe)
• Articolo in rivista (Classe)

Label

• Nitroxyl peptides as catalysts of enantioselective oxidations (Articolo in rivista) (literal)

Anno

• 2002-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1002/1521-3765(20020104)8:1<84::AID-CHEM84>3.0.CO;2-N (literal)

Alternative label

• Formaggio F., Bonchio M., Crisma M., Peggion C., Mezzato S., Polese A., Barazza A., Antonello S., Maran F., Broxterman Q.B., Kaptein B., Kamphuis J., Vitale R.M., Saviano M., Benedetti E., Toniolo C. (2002)
  Nitroxyl peptides as catalysts of enantioselective oxidations
  in Chemistry (Weinh., Print)
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Formaggio F., Bonchio M., Crisma M., Peggion C., Mezzato S., Polese A., Barazza A., Antonello S., Maran F., Broxterman Q.B., Kaptein B., Kamphuis J., Vitale R.M., Saviano M., Benedetti E., Toniolo C. (literal)

Pagina inizio

• 84 (literal)

Pagina fine

• 93 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#altreInformazioni

• Citazioni WOS: 32 Impact Factor 2002: 4.238 Coautore (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 8 (literal)

Rivista

• Chemistry (Rivista)

Note

• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• Univ Padua, Dept Organ Chem, CNR, Ctr CSB, I-35131 Padua, Italy; Univ Padua, CNR, Ctr CMRO, Dept Organ Chem, I-35131 Padua, Italy; Univ Padua, Dept Phys Chem, I-35131 Padua, Italy; DSM Research, Organ Chem & Biotechnol Sect, NL-6160 MD Geleen, Netherlands; DSM Food Specialties, Nutrit Ingredients, NL-2600 Delft, Netherlands; 2nd Univ Naples, Dept Environm Sci, I-81100 Caserta, Italy; Univ Naples Federico II, Dept Chem, CNR, Biocrystallog Res Ctr, I-80134 Naples, Italy; (literal)

Titolo

• Nitroxyl peptides as catalysts of enantioselective oxidations (literal)

Abstract

• 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-(alpha Me)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. (literal)

Prodotto di

• Istituto di chimica biomolecolare (ICB) (Istituto)
• Institute on membrane technology (ITM) (Istituto)

Autore CNR

• MARCO CRISMA (Unità di personale interno)
• MICHELE SAVIANO (Persona)
• MARCELLA BONCHIO (Persona)

Incoming links:

Prodotto

• Institute on membrane technology (ITM) (Istituto)
• Istituto di chimica biomolecolare (ICB) (Istituto)

Autore CNR di

• MARCO CRISMA (Unità di personale interno)
• MICHELE SAVIANO (Persona)
• MARCELLA BONCHIO (Persona)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Chemistry (Rivista)