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Synthesis of Chiral α-Trifluoromethyl α,α-Disubstituted α-Amino Acids and Conformational Analysis of L-Leu-Based Peptides with (R)- or (S)-α-Trifluoromethylalanine


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Title: Synthesis of Chiral α-Trifluoromethyl α,α-Disubstituted α-Amino Acids and Conformational Analysis of L-Leu-Based Peptides with (R)- or (S)-α-Trifluoromethylalanine
Authors: Ueda, Atsushi / Ikeda, Misuzu / Kasae, Takuya / Doi, Mitsunobu / Demizu, Yosuke / Oba, Makoto / Tanaka, Masakazu
Issue Date: 15-Sep-2020
Publisher: Wiley-VCH GmbH
Citation: ChemistrySelect, 5(35), pp.10882-10886; 2020
Abstract: Various racemic α-trifluoromethyl α,α-disubstituted α-amino acids were synthesized by the reaction of methyl 3,3,3-trifluoropyruvate imines with Grignard reagents. The optical resolution of racemates using (R)-1,1’-bi-2-naphthol {(R)-BINOL} esters gave optically active α-trifluoromethylated α,α-disubstituted α-amino acids, such as α-trifluoromethylalanine (αCF3Ala), α-trifluoromethylleucine (αCF3Leu), and α-trifluoromethylphenylalanine (αCF3Phe). The optically active (R)- or (S)-αCF3Ala was incorporated into the L-Leu-based pentapeptides, and their preferred conformation in solution and in the crystal state was studied by Fourier transform infrared (FT-IR) absorption, nuclear Overhauser effect spectroscopy (NOESY) NMR, and circular dichroism (CD) spectra, as well as X-ray crystallographic analysis. Both L–Leu-based peptides with (R)- or (S)-αCF3Ala formed right-handed 310-helical structures. Both peptide-backbones at the N-terminal residues 1-3 were very similar, but the φ and ψ torsion angles of residues 4 and 5 between peptides with (R)- or (S)- αCF3Ala were different.
Keywords: amino acid / conformation / helix / peptide / trifluoromethy
URI: http://hdl.handle.net/10069/40319
ISSN: 23656549
DOI: 10.1002/slct.202002888
Rights: © 2020 Wiley-VCH GmbH. This is the peer reviewed version of the following article: ChemistrySelect, 5(35), pp.10882-10886; 2020 which has been published in final form at https://doi.org/10.1002/slct.202002888. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/40319

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