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Merck

Gamma-fluorinated analogues of glutamic acid and glutamine.

Amino acids (2003-04-23)
R Dave, B Badet, P Meffre
ABSTRACT

Gamma-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.

MATERIALS
Product Number
Brand
Product Description

Supelco
L-Glutamic acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Supelco
L-Glutamic acid, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
L-Glutamic acid, BioUltra, ≥99.5% (NT)
Sigma-Aldrich
L-Glutamic acid, FCC
Sigma-Aldrich
(R)-(+)-3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, 95%
Sigma-Aldrich
L-Glutamic acid, from non-animal source, meets EP testing specifications, suitable for cell culture, 98.5-100.5%
Sigma-Aldrich
L-Glutamic acid, ReagentPlus®, ≥99% (HPLC)
Glutamic acid, European Pharmacopoeia (EP) Reference Standard