Nitroxyl peptides as catalysts of enantioselective oxidations (583 views)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2002; 8(1): [d]84-93.
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Paper type: Journal Article,
Impact factor: 4.238, 5-year impact factor: 5.608
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0037016790&partnerID=40&md5=eb49bc7b5dd6b6ec669b6959031ef518
Keywords: 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,
Affiliations:
*** 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
References:
Not available.
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2002; 8(1): [d]84-93.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 4.238, 5-year impact factor: 5.608
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0037016790&partnerID=40&md5=eb49bc7b5dd6b6ec669b6959031ef518
Keywords: 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,
Affiliations:
*** 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
References:
Not available.
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.
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
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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 (655 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2001; 7(1): 15-26.
Impact Factor: 1.451
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* Crystal-state conformation of Cα, α-dialkylated peptides containing chiral β-homo-residues (655 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2001; 7(1): 15-26.
Impact Factor: 1.451
View Export to BibTeX Export to EndNote
1 Records (1 excluding Abstracts).
Total impact factor: 1.451 (1.451 excluding Abstracts).
Total 5 year impact factor: 1.715 (1.715 excluding Abstracts).
Total impact factor: 1.451 (1.451 excluding Abstracts).
Total 5 year impact factor: 1.715 (1.715 excluding Abstracts).
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