Open AccessJournal Article
Synthesis, characterization, and solution conformational analysis of C alpha-methyl-, C alpha-benzylglycine [(alpha Me)Phe] model peptides.
Claudio Toniolo,Fernando Formaggio,Marco Crisma,Gian Maria Bonora,Pegoraro S,Polinelli S,Wilhelmus H. J. Boesten,Hans E. Schoemaker,Quirinus B. Broxterman,Johan Kamphuis +9 more
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TL;DR: The results of the solution conformational analysis support the view that the (alpha Me)Phe residue is a stronger beta-turn and helix promoter than the unmethylated Phe analog.
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Abstract: We have synthesized, by solution methods, and fully characterized a variety of (alpha Me)Phe derivatives and model peptides (to the pentapeptide level). The results of the solution conformational analysis, performed by using infrared absorption and 1H nuclear magnetic resonance, support the view that the (alpha Me)Phe residue is a stronger beta-turn and helix promoter than the unmethylated Phe analog. A comparison is also made with the conclusions extracted from published work on peptides rich in other C alpha-alkylglycyl residues.
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Citations
Structures of peptides from alpha-amino acids methylated at the alpha-carbon.
Claudio Toniolo,Marco Crisma,Fernando Formaggio,G. Valle,Giorgio Cavicchioni,Gilles Precigoux,André Aubry,Johan Kamphuis +7 more
Abstract: The structural preferences of peptides (and depsipeptides) from the achiral MeAib and Hib residues, and the chiral Iva, (alpha Me) Val, (alpha Me) Leu, and (alpha Me) Phe residues, as determined by conformational energy computations, x-ray diffraction analyses, and 1H-nmr and spectroscopic studies, are reviewed and compared with literature data on Aib-containing peptides. The results obtained indicate that helical structures are preferentially adopted by peptides rich in these alpha-amino acids methylated at the alpha-carbon. Intriguing experimental findings on the impact of the chirality of Iva, (alpha Me) Val, and (alpha Me) Phe residues on helix screw sense are illustrated.
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High-performance liquid chromatographic separation of the enantiomers of unusual α-amino acid analogues
Antal Péter,Edit Olajos,Richard Casimir,Dirk Tourwé,Quirinus B. Broxterman,Bernard Kaptein,Daniel W. Armstrong +6 more
TL;DR: Of the two indirect methods, GITC derivatization seemed more effective than FDAA derivatized, while the teicoplanin-based Chirobiotic T column was efficient in the separation of ring- and alpha-methyl-substituted phenylalanine analogues, but was ineffective for the amides of these analogues.
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Bioactive and model peptides characterized by the helicogenic (αMe)Phe residue
Claudio Toniolo,Fernando Formaggio,Marco Crisma,Giovanni Valle,Wilhelmus H. J. Boesten,Hans E. Schoemaker,Johan Kamphuis,Piero Andrea Temussi,Elmer L. Becker,Gilles Precigoux +9 more
TL;DR: The hypersweet super-aspartame analogue p CN-C6H4-NHCO-L-Asp-L-(αMe)Phe-OME 1, the first D-chemotactic peptide being found more active than its L-diastereomer, is synthesized and fully characterized.
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