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Practical synthesis of L-erythro- and L-threo-4-fluoroglutamic acids using aminoacylase

✍ Scribed by Yoshitsugu Kokuryo; Takuji Nakatani; Kobee Kobayashi; Yoshinori Tamura; Kenji Kawada; Mitsuaki Ohtani

Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
403 KB
Volume
7
Category
Article
ISSN
0957-4166

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✦ Synopsis

Enantiomerically pure L-erythroand L-threo-4-fluoroglutamic acids la and lb 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 T-carboxyl group as a methyl ester was found to be crucial for this enzymatic reaction.

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