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Synthesis of both enantiomers of cyclic methionine analogue: (R)- and (S)-3-aminotetrahydrothiophene-3-carboxylic acids
http://hdl.handle.net/10069/32538
http://hdl.handle.net/10069/32538a57378d0-b863-47e3-9c47-b0119922a63b
名前 / ファイル | ライセンス | アクション |
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TetAsy24_464.pdf (167.6 kB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2013-06-28 | |||||
タイトル | ||||||
タイトル | Synthesis of both enantiomers of cyclic methionine analogue: (R)- and (S)-3-aminotetrahydrothiophene-3-carboxylic acids | |||||
言語 | ||||||
言語 | eng | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | cyclic α,α-disubstituted α-amino acid | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | methionine analogue | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | optical resolution | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | chiral amino acid | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | unnatural amino acid | |||||
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 |
Oba, Makoto
× Oba, Makoto× Shimabukuro, Atsushi× Ono, Miyako× Doi, Mitsunobu× Tanaka, Masakazu |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | A method of synthesizing an optically active cyclic methionine analogue, 3-aminotetrahydrothiophene-3-carboxylic acid (At5c), is described. A Bucherer-Bergs reaction of 4,5-dihydro-3(2H)-thiophenone and the subsequent alkaline hydrolysis of a hydantoin, followed by Cbz protection of the amine, afforded racemic Cbz-At5c (±)-3 in excellent yield. Diastereomeric esters derived from Cbz-At5c (±)-3 and (R)-BINOL could be separated by column chromatography to give both diastereomers with >99% de. X-ray crystallographic analysis revealed the absolute configuration of the synthesized amino acid derived from the less polar diastereomeric ester to be (S). | |||||
書誌情報 |
Tetrahedron: Asymmetry 巻 24, 号 8, p. 464-467, 発行日 2013-04-30 |
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出版者 | ||||||
出版者 | Elsevier Limited | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 09574166 | |||||
DOI | ||||||
関連タイプ | isVersionOf | |||||
識別子タイプ | DOI | |||||
関連識別子 | 10.1016/j.tetasy.2013.03.010 | |||||
権利 | ||||||
権利情報 | © 2013 Elsevier Ltd. All rights reserved. | |||||
権利 | ||||||
権利情報 | NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron: Asymmetry. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron: Asymmetry, 24, 8(2013) | |||||
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 | Tetrahedron: Asymmetry, 24(8), pp.464-467; 2013 |