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