- Practical synthesis of L-erythro- and L-threo-4-fluoroglutamic acids using aminoacylase
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Enantiomerically pure L-erythro- and L-threo-4-fluoroglutamic acids 1a and 1b were conveniently prepared. The key steps in this synthesis relied upon separation of diastereomers of N-chloroacetyl-4-fluoroglutamic acid 5-methyl ester 7 by recrystallization and enzymatic resolution of enantiomers of the resulting 7(a+c) and 7(b+d) by aminoacylase. Protection of the γ-carboxyl group as a methyl ester was found to be crucial for this enzymatic reaction.
- Kokuryo, Yoshitsugu,Nakatani, Takuji,Kobayashi, Kobee,Tamura, Yoshinori,Kawada, Kenji,Ohtani, Mitsuaki
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- [F-18]-labeled L-glutamic acid, [F-18]-labeled L-glutamine, derivatives thereof and use thereof and processes for their preparation
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The compounds and the synthesis of [F-18]-labeled L-glutamic acid, [F-18]-labeled L-glutamate, their derivatives as set forth in formula (I) and their uses are described.
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Page/Page column 37; 38
(2016/08/03)
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- [F-18]-LABELED L-GLUTAMIC ACID, [F-18]-LABELED L-GLUTAMINE, DERIVATIVES THEREOF AND USE THEREOF AND PROCESSES FOR THEIR PREPARATION
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The compounds and the synthesis of [F-18]-labeled L-glutamic acid, [F-18]-labeled L-glutamate, their derivatives as set forth in formula (I) and their uses are described.
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Paragraph 0890
(2016/12/01)
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- [F-18]-LABELED L-GLUTAMIC ACID, [F-18]-LABELED L-GLUTAMINE, DERIVATIVES THEREOF AND USE THEREOF AND PROCESSES FOR THEIR PREPARATION
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The compounds and the synthesis of [F-18]-labeled L-glutamic acid, [F-18]-labeled L-glutamate, their derivatives as set forth in formula (I) and their uses are described.
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- New stereospecific syntheses and x-ray diffraction structures of (-)-D-erythro- And (+)-L-threo-4-fluoroglutamic acid
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Stereospecific syntheses of (+)-L-threo and (-)-D-erythro-4-fluoroglutamic acid are based on the hydrolysis of methyl 1-acetyl-4-fluoro-L-pyrrolidin-5-one-2-carboxylate, prepared from trans- and cis-4-hydroxyprolines, respectively.
- Hudlicky, Milos,Merola, Joseph S.
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p. 7403 - 7406
(2007/10/02)
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- Resolution of γ-Methyl and γ-Fluoroglutamic Acids. Lack of Stereospecificity of Leucine Aminopeptidase with L-Leucyl-L-erythro-γ-substituted Glutamates
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The hydrolysis of L-leucyl-γ-substituted D,L-glutamates by leucine aminopeptidase, from porcine kidney, is stereospecific with threo-γ-methyl and threo-γ-fluoroglutamate containing dipeptides whereas there is a lack of stereospecificity with erythro-isomers.The optical purities of L-threo- and L-erythro-glutamate isomers thus obtained have been monitored by gas chromatography, high pressure liquid chromatography, or nuclear magnetic resonance.The optical rotations of optically pure L-isomers have been measured and the discrepancies with former publications are discussed.
- Bory, Sonia,Dubois, Joelle,Gaudry, Michel,Marquet, Andree,Lacombe, Liliane,Weinstein, Shulamith
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p. 475 - 480
(2007/10/02)
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