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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
http://hdl.handle.net/10069/40319
http://hdl.handle.net/10069/40319fc3440e2-af26-4510-b937-6e0f99b0d236
名前 / ファイル | ライセンス | アクション |
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ChemSelect5_10882.pdf (776.6 kB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2020-12-16 | |||||
タイトル | ||||||
タイトル | 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 | |||||
言語 | ||||||
言語 | eng | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | amino acid | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | conformation | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | helix | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | peptide | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | trifluoromethy | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者 |
Ueda, Atsushi
× Ueda, Atsushi× Ikeda, Misuzu× Kasae, Takuya× Doi, Mitsunobu× Demizu, Yosuke× Oba, Makoto× Tanaka, Masakazu |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | 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. |
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書誌情報 |
ChemistrySelect 巻 5, 号 35, p. 10882-10886, 発行日 2020-09-15 |
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出版者 | ||||||
出版者 | Wiley-VCH GmbH | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 23656549 | |||||
EISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 23656549 | |||||
DOI | ||||||
関連タイプ | isVersionOf | |||||
識別子タイプ | DOI | |||||
関連識別子 | 10.1002/slct.202002888 | |||||
権利 | ||||||
権利情報 | c 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. | |||||
著者版フラグ | ||||||
出版タイプ | AM | |||||
出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||
引用 | ||||||
内容記述タイプ | Other | |||||
内容記述 | ChemistrySelect, 5(35), pp.10882-10886; 2020 |