Document Detail

Gamma-fluorinated analogues of glutamic acid and glutamine.
MedLine Citation:
PMID:  12707806     Owner:  NLM     Status:  MEDLINE    
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.
R Dave; B Badet; P Meffre
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Review    
Journal Detail:
Title:  Amino acids     Volume:  24     ISSN:  0939-4451     ISO Abbreviation:  Amino Acids     Publication Date:  2003 Apr 
Date Detail:
Created Date:  2003-04-22     Completed Date:  2004-03-09     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9200312     Medline TA:  Amino Acids     Country:  Austria    
Other Details:
Languages:  eng     Pagination:  245-61     Citation Subset:  IM    
UMR 7573-C.N.R.S., ENSCP, 11 rue Pierre et Marie Curie, F-75231 Paris Cedex 05, France.
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MeSH Terms
Fluorine / chemistry*
Glutamic Acid / analogs & derivatives,  chemical synthesis*,  chemistry
Glutamine / analogs & derivatives,  chemical synthesis*,  chemistry
Models, Chemical
Molecular Structure
Reg. No./Substance:
56-85-9/Glutamine; 56-86-0/Glutamic Acid; 7782-41-4/Fluorine

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