Nitroxyl peptides as catalysts of enantioselective oxidations(423 views 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
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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Nitroxyl peptides as catalysts of enantioselective oxidations
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.
Nitroxyl peptides as catalysts of enantioselective oxidations
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Nitroxyl peptides as catalysts of enantioselective oxidations
2 Records (2 escludendo Abstract e Conferenze). Impact factor totale: 3.931 (3.931 escludendo Abstract e Conferenze). Impact factor a 5 anni totale: 4.39 (4.39 escludendo Abstract e Conferenze).
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