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Article Dans Une Revue Amino Acids Année : 2003

γ-Fluorinated analogues of glutamic acid and glutamine

Résumé

γ-Fluorinated analogues of glutamic acid and glutamine are compounds of biological interest. Syntheses of such compounds are extensively reviewed in this article. 4-Fluoroglutamic acid was prepared as a mixture of racemic diastereomers by Michael reaction, inverse-Michael reaction or by electrophilic / nucleophilic fluorination. Optically enriched 4-fluoroglutamic acids were obtained by several resolution techniques as well as by asymmetric methodologies using the chiral pool. 4-Fluoroglutamine was prepared as a mixture of stereoisomers as well as in racemic erythro and threo forms from the corresponding 4-fluoroglutamic acids using aminolysis and conventional protection and deprotection strategies. Racemic 4,4-difluoroglutamic acid was synthesized by a nitroaldol reaction and its L-enantiomer obtained via three different asymmetric routes. Racemic 4,4-difluoroglutamic acid was converted into the corresponding 4,4-difluoroglutamine using a protection / aminolysis / deprotection sequence while N-Boc-L-4,4-difluoroglutamine was prepared directly from (R)-Garner's aldehyde using a Reformatsky reaction as the key step.
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Dates et versions

hal-02002676 , version 1 (11-02-2019)

Identifiants

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R. Dave, B. Badet, Patrick Meffre. γ-Fluorinated analogues of glutamic acid and glutamine. Amino Acids, 2003, 24 (3), pp.245-261. ⟨10.1007/s00726-002-0410-9⟩. ⟨hal-02002676⟩
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