Optical resolution of DL-valine, DL-leucine, and DL-isoleucine by formation of adduct with L-phenylalanine.

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概要

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• An alkaline solution containing L-phenylalanine (L-Phe) and one of DL-valine, DL-leucine, and DL-isoleucine is allowed to selectively form a precipitate composed of L-Phe and the aliphatic D-amino acid by adjusting the pH of initial solution to around 5.5 with hydrochloric acid. <SUP>1</SUP>H NMR spectra in deuterium oxide, elemental analyses, and infrared spectra of the precipitates indicate that they are adducts of the aliphatic D-amino acid and L-Phe in the molar ratio of 1:1. The free aliphatic DL-amino acids with high optical purity (84–100%) may be recovered from the adducts in 49–63% yield. An attempt was made to obtain both the aliphatic D- and DL-amino acids by using an aqueous solution containig the aliphatic DL-amino acid and L-Phe as an initial solution. The aliphatic L-amino acids obtained had optical purity of 47–85%.

• 公益社団法人 日本化学会の論文

著者

• KUROKAWA Hidemoto

  Faculty of Engineering and High Technology Research Center, Kansai University

• Shiraiwa Tadashi

  Faculty Of Chemistry Materials And Bioengineering Kansai University

• Sakaguchi Keiji

  Faculty of Engineering, Kansai University

• Ikawa Akihiko

  Faculty of Engineering, Kansai University

関連論文

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• Optical Resolution by Preferential Crystallization of(RS)-α-Amino-γ-butyrolactone Hydrochloride
• Optical Resolution by Preferential Crystallization of (RS)-Bromosuccinic Acid
• Structures and Properties of a Diastereoisomeric Molecular Compound of (2S,3S)- and (2R,3S)-N-Acetyl-2-amino-3-methylpentanoic Acids
• Preparation of Optically Active Allothreonine by Separating from a Diastereoisomeric Mixture with Threonine
• Asymmetric transformation of (RS)-cysteine via formation of (RS)-4-thiazolidinecarboxylic acids.
• Optical resolution by preferential crystallization of DL-thiazolidine-4-carboxylic acid.
• Asymmetric Transformation of (RS)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic Acid via Salt Formation with (1S)-10-Camphorsulfonic Acid.
• Asymmetric transformation of (RS)-2-phenylglycine via formation of salt with(1S)-10-camphorsulfonic acid.
• Facile Production of D-Histidine by Asymmetric Transformation of L-Histidine.
• Racemic structure and optical resolution by preferential crystallization of (.+-.)-organic ammonium hydrogen malates.
• Asymmetric Transformations of Proline and 2-Piperidinecarboxylic acid via Formation of Salts with Optically Active Tartaric Acid.
• Optical resolution of DL-valine, DL-leucine, and DL-isoleucine by formation of adduct with L-phenylalanine.
• Racemic structures and optical resolutions by preferential crystallization of organic ammonium salts of N-formyl-DL-phenylalanine.
• Optical resolution by replacing crystallization of ammonium salts of N-acetyl-DL-2-aminobutanoic acid, N-acetyl-DL-norvaline, and N-acetyl-DL-norleucine.
• Racemic structures and optical resolution by preferential crystallization of organic ammonium salts of (.+-.)-mandelic acid.
• Racemic structure and optical resolution by preferential crystallization of DL-cysteine salts of substituted benzenesulfonic acids.
• Optical resolution of (.+-.)-phenylsuccinic acid by using (-)-proline as resolving agent.
• Racemic structure and optical resolution by preferential crystallization of organic ammonium salts of N-formyl-DL-tyrosine.
• Optical resolution by preferential crystallization of 1,1,3,3-tetramethylbutylammonium salt of N-formyl-DL-.ALPHA.-phenylglycine.
• Optical resolution by replacing crystallization of DL-threonine.

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