Structures and Properties of a Diastereoisomeric Molecular Compound of (2S,3S)- and (2R,3S)-N-Acetyl-2-amino-3-methylpentanoic Acids

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概要

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• An X-ray crystal structural analysis revealed that (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid (N-acetyl-L-isoleucine; Ac-L-Ile) and (2R,3S)-N-acetyl-2-amino-3-methylpentanoic acid (N-acetyl-D-alloisoleucine; Ac-D-aIle) formed a molecular compound containing one Ac-L-Ile molecule and one Ac-D-aIle molecule as an unsymmetrical unit. This molecular compound is packed with strong hydrogen bonds forming homogeneous chains consisting of Ac-L-Ile molecules or Ac-D-aIle molecules and weak hydrogen bonds connecting these homogeneous chains in a fashion similar to that observed for Ac-L-Ile and Ac-D-aIle. Recrystallization of an approximately 1:1 mixture of Ac-L-Ile and Ac-D-aIle from water gave an equimolar molecular compound due to its lower solubility than that of Ac-D-aIle or especially Ac-L-Ile. The results suggest that the equimolar mixture of Ac-L-Ile and Ac-D-aIle could be obtained from an Ac-L-Ile-excess mixture by recystallization from water.

• 社団法人 日本農芸化学会の論文
• 2009-10-23

著者

• Yajima Tatsuo

  Fac. Of Chemistry Materials And Bioengineering Kansai Univ.

• Yajima Tatsuo

  Faculty Of Chemistry Materials And Bioengineering Kansai University

• Shiraiwa Tadashi

  Faculty Of Chemistry Materials And Bioengineering Kansai University

• KIMURA Makiko

  Faculty of Chemistry, Materials and Bioengineering, Kansai University

• NAKAKOJI Mami

  Faculty of Chemistry, Materials and Bioengineering, Kansai University

• HORIKAWA Takao

  Faculty of Chemistry, Materials and Bioengineering, Kansai University

• TOKUYAMA Yurie

  Faculty of Chemistry, Materials and Bioengineering, Kansai University

• Nakakoji Mami

  Faculty Of Chemistry Materials And Bioengineering Kansai University

• Horikawa Takao

  Faculty Of Chemistry Materials And Bioengineering Kansai University

• Tokuyama Yurie

  Faculty Of Chemistry Materials And Bioengineering Kansai University

• Kimura Makiko

  Faculty Of Chemistry Materials And Bioengineering Kansai University

関連論文

• Optical Resolution by Preferential Crystallization of (RS)-2-Amino-3-(2-carboxyethylthi0) propanoic Acid
• Optical Resolution by Preferential Crystallization of(RS)-α-Amino-γ-butyrolactone Hydrochloride
• Optical Resolution by Preferential Crystallization of (RS)-Bromosuccinic Acid
• Preparation of Optically Active 2-Aminobutanoic Acid via Optical Resolution by Replacing Crystallization
• 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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