γ-fluorinated analogues of glutamic acid and glutamine

Amino Acids

Volumn 24, Issue 3, 2003, Pages 245-261

  Dave, R ^a   Badet, B ^b   Meffre, Patrick ^a  

^a PSL RESEARCH UNIVERSITY   (France)

^b INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

, Diflu orinated glutamic acid; Fluorinated glutamic acid; Fluorinated glutamine; 4 Fluoroglutamic acid; 4 Fluoroglutamine; 4 Fluoromethotrexate; Glutamine; Glutamine dependent amidotransferase

Indexed keywords

4 FLUOROGLUTAMIC ACID; 4 FLUOROGLUTAMINE; 4,4 DIFLUOROGLUTAMIC ACID; GLUTAMIC ACID DERIVATIVE; GLUTAMINE; UNCLASSIFIED DRUG;

ALDOL REACTION; AMINO ACID SYNTHESIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; FLUORINATION; METHODOLOGY; MICHAEL ADDITION; OPTICAL ROTATION; PRIORITY JOURNAL; REACTION ANALYSIS; REFORMATSKY REACTION; REVIEW; STEREOISOMERISM;

FLUORINE; GLUTAMIC ACID; GLUTAMINE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0038070590     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-002-0410-9     Document Type: Review

References (59)

1. Alekseeva LV, Lundin BN, Burde NL (1967) Synthesis and investigation of compounds with potential biological activity I. Synthesis of 4-fluoroglutamic acid. Zh Obshch Khim 37: 1754-1755
2. Ardawi MSM, Newsholme EA (1983) Glutamine metabolism in lymphocyte of the rat. Biochem J 212: 835-842
3. Avent AG, Bowler AN, Doyle PM, Marchand CM, Young DW (1992) Stereospecific synthesis of 4-fluoroglutamic acids. Tetrahedron Lett 33: 1509-1512
4. Bergmann ED, Chun-Hsu L (1973) Organic fluorine compounds; Part XLVI. γ-Fluoroglutamic acid and fluorofolic acid. Synthesis: 44-46
5. Bergmann ED, Cohen S, Shani A (1963) Organic fluorine compounds. Part XXX. Experiments in the fluoroglutaric acid series. Israel J Chem 1: 79-85
6. Blaskovich MA, Evindar G, Rose NGW, Wilkinson S, Luo Y, Lajoie GA (1998) Stereoselective synthesis of threo and erythro β-hydroxy and β-disubstituted-β-hydroxy α-amino acids. J Org Chem 63: 3631-3646
7. Bory S, Dubois J, Gaudry M, Marquet A (1984) Resolution of γ-methyl and γ-fluoroglutamic acids. Lack of stereospecificity of leucine aminopeptidase with L-leucyl-L-erythro-γ-substituted glutamates. J Chem Soc Perkin Trans 1: 475-480
8. Buchanan RL, Dean FH, Pattison FLM (1962) γ-Fluoroglutamic acid. Can J Chem 40: 1571-1575
9. Castell LM, Newsholme EA (2001) The relation between glutamine and the immunodepression observed in exercise. Amino Acids 20: 49-61
10. Ding Y, Wang J, Abboud K, Xu Y, Dolbier W, Richards N (2001) Synthesis of L-4,4-difluoroglutamic acid via nucleophilic addition to a chiral aldehyde. J Org Chem 66: 6381-6188
11. Drsata J, Netopilova M, Tolman V (1999) Stereoisomers of 4-fluoroglutamic acid: influence on Escherichia coli glutamate decarboxylase. Pharmazie 54: 713-714
12. Drsata J, Netopilova M, Tolman V (2000) Influence of stereoisomers of 4-fluoroglutamate on rat brain glutamate decarboxylase. J Enzyme Inhibition 15: 273-282
13. Dubois J, Gaudry M, Bory S, Azerad R, Marquet A (1983) Vitamin K-dependent carboxylation. Study of the hydrogen abstraction stereochemistry with γ-fluoroglutamic acid-containing peptides. J Biol Chem 258: 7897-7899
14. Garner P, Park J (1992) 1,1-Dimethylethyl (S)- or (R)-4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate: a useful serinal derivative. Org Synth 70: 18-28
15. Hart B, Haile W, Licato N, Bolanowska W, McGuire J, Coward J (1996) Synthesis and biological activity of folic acid and methotrexate analogues containing L-threo-(2S,4S)-4-fluoroglutamic acid and DL-3,3-difluoroglutamic acid. J Med Chem 39: 56-65
16. Haufe G, Kroger S (1996) Syntheses of γ-fluoro-α-amino acids. Amino Acids 11: 409-424
17. Hudlicky M (1960) The synthesis of γ-fluoroglutamic acid. Tetrahedron Lett 1: 21-22
18. Hudlicky M (1961) Organic compounds of fluorine. II. Fluorinated amino acids. Coll Czech Chem Commun 26: 1414-1421
19. Hudlicky M (1991) Stereospecific synthesis of (+)-L-erythro-4-fluoroglutamic acid. Tema con variazioni. J Fluorine Chem 54: 194
20. Hudlicky M (1992) Chemistry of organic fluorine compounds, 2nd edn. Ellis Horwood Ltd., Chichester
21. Hudlicky M (1993) Stereospecific synthesis of all four stereoisomers of 4-fluoroglutamic acid. J Fluorine Chem 60: 193-210
22. Hudlicky M, Merola J (1990) New stereospecific syntheses and X-ray diffraction structures of (-)-D-erythro- and (+)-L-threo-4-fluoroglutamic acid. Tetrahedron Lett 31: 7403-7406
23. Hudlicky M, Merola J (1991) Corrigendum. Tetrahedron Lett 32: 3134
24. Kaneko T, Lee YK, Hanafusa T (1962) Syntheses of γ-hydroxyglutamic acid. Bull Chem Soc Jpn 35: 875-878
25. Kitagawa O, Hashimoto A, Kobayashi Y, Taguchi T (1990) Michael addition of 2,2-difluoroketene silyl acetal. Preparation of 4,4-difluoroglutamic acid and 5,5-difluorolysine. Chem Lett 1307-1310
26. Kobayashi Y, Taguchi T, Kitagawa O, Hashimoto T, Miura A (1991) Preparation of 2,2-difluorocarboxylic acid derivatives. JP03027325
27. Kokuryo Y, Nakatani T, Kobayashi K, Tamura Y, Kawada K, Ohtani M (1996) Practical synthesis of L-erythro- and L-threo-4-fluoroglutamic acids using aminoacylase. Tetrahedron: Asymmetry 7: 3545-3551
28. Konas DW, Coward JK (1999) Synthesis of L-4,4-difluoroglutamic acid via electrophilic difluorination of a lactam. Org Lett 1: 2105-2107
29. Konas DW, Coward JK (2001) Electrophilic fluorination of pyroglutamic acid derivatives: Application of substrate-dependent reactivity and diastereoselectivity to the synthesis of optically active 4-fluoroglutamic acids. J Org Chem 66: 8831-8842
30. Kukhar VP, Soloshonok VA (1995) Fluorine-containing amino acids. Synthesis and properties. John Wiley and Sons, Chichester
31. Licato NJ, Coward JK, Nimec Z, Galivan J, Bolanowska WE, McGuire JJ (1990) N-[N-(4-deoxy-4-amino-10-methylpteroyl)-4-fluoroglutamyl]-γ -glutamate, an unusual substrate for folylpoly-γglutamate synthetase and γ-glutamyl hydrolase. J Med Chem 33: 1022-1027
32. Massiere F, Badet-Denisot M-A (1998) The mechanism of glutamine-dependent amidotransferases. Cell Mol Life Sci 54: 205-222
33. Maurs M, Ducrocq C, Righini-Tapie A, Azerad R (1985) Gas chromatographic resolution of substituted glutamic acid enantiomers. J Chromatogr 325: 444-449
34. Meffre P, Dave R, Leroy J, Badet B (2001) A concise synthesis of L-4,4-difluoroglutamine. Tetrahedron Lett 42: 8625-8627
35. Meffre P, Dave R, Leroy J, Badet B (2002) Corrigendum to "A concise synthesis of L-4,4-difluoroglutamine" Tetrahedron Lett 43: 6279
36. Meffre P, Durand P, Branquet E, Le Goffic F (1994) A straightforward synthesis of N-Boc-L-serinal and N-Boc-L-threoninal acetonides. Synth Commun 24: 2147-2152
37. Ohta T, Hosoi A, Nozoe S (1988) Stereoselective hydroxylation of N-carbamoyl-L-pyroglutamate. Synthesis of (-)-Bulgecinine. Tetrahedron Lett 29: 329-332
38. Picketing L, Malhi BS, Coe PL, Walker RT (1994) The synthesis of 4′-t-butylcarbamyl- and 4′-p-toluenesulphonamidyl-2′,3′-dideoxypyrimidi ne nucleoside analogues. Nucleosides Nucleotides 13: 1493-1506
39. Piper JR, Montgomery JA (1977) Preparation of 6-(bromomethyl)-2,4-pteridinediamine hydrobromide and its use in improved syntheses of methotrexate and related compounds. J Org Chem 42: 208-211
40. Sutherland A, Willis CL (2000) Synthesis of fluorinated amino acids. Nat Prod Rep 17: 621-631
41. Teplyakov A, Leriche C, Obmolova G, Badet B, Badet-Denisot M-A (2002) From Lobry de Bruyn to enzyme-catalyzed ammonia channelling: molecular studies of D-glucosamine-6P synthase. Nat Prod Rep 19: 60-69
42. Tolman V (1964) Monofluorinated analogues of amino acids. Tetrahedron Lett 5: 1967-1969
43. Tolman V (1993) Chemistry of 4-fluoroglutamic acid. Part 1. A critical survey of its syntheses: an attempt to optimize reaction conditions for large-scale preparation. J Fluorine Chem 60: 179-183
44. Tolman V (1996) Syntheses of fluorinated amino acids from the classical to the modern concept. Amino Acids 11: 15-36
45. Tolman V, Sedmera P (2000) Chemistry of 4-fluoroglutamic acid. Part 3. Preparation of the diastereomers of 4-fluoroglutamine and 4-fluoroisoglutamine. An enzymatic access to the antipodes of 4-amino-2-fluorobutyric acid. J Fluorine Chem 101: 5-10
46. Tolman V, Simek P (2000) Chemistry of 4-fluoroglutamic acid. Part 4. Resolution of the racemic erythro and threo forms through their diastereomeric salts. J Fluorine Chem 101: 11-14
47. Tolman V, Spronglova P (1983) Synthesis of 2-fluoropropenoic acid derivatives. Collect Czech Chem Commun 48: 319-326
48. Tolman V, Veres K (1964) Synthese und einige reaktionen des 2-fluor-3-hydroxypropionsäure-äthylesters. Collect Czech Chem Commun 29: 234-238
49. Tolman V, Veres K (1966) Potential antimetabolites derived from 4-fluoroglutamic acid. Tetrahedron Lett 7: 3909-3912
50. Tolman V, Veres K (1967) Synthesis of certain monofluorinated aliphatic amino acids. Coll Czech Chem Commun 32: 4460-4469
51. Tolman V, Vlasakova V, Zivny K (1984) Simple method for the separation of diastereomers of 4-fluoroglutamic acid by gas-liquid chromatography. J Chromatogr 315: 421-424
52. Tolman V, Vlasakova V, Zivny K (1985) Preparative separation of 4-fluoroglutamic acid stereoisomers. J Fluorine Chem 29: 138
53. Tolman V, Vlasakova V, Nemecek J (1993) Chemistry of 4-fluoroglutamic acid. Part 2. Separation of the diastereomers on a large scale. Preparation of cis- and trans-4-fluoro-5-pyrrolidone-2-carboxylic acids (4-fluoropyroglutamic acids). J Fluorine Chem 60: 185-191
54. Tsukamoto T, Coward J (1996) Facile synthesis of DL-difluoroornithine, DL-4,4-difluoroglutamine, and γ-DL-4,4-difluoroglutamyl-containing peptides: Regiospecific addition of nucleophiles to N-Cbz-di-tert-butyl-DL-4,4-difluoroglutamate. J Org Chem 61: 2497-2500
55. Tsukamoto T, Kitazume T, McGuire J, Coward J (1996) Synthesis and biological evaluation of DL-4,4-difluoroglutamic acid and DL-γ,γ-difluoromethotrexate. J Med Chem 39: 66-72
56. Tsushima T, Kawada K, Ishihara S, Uchida N, Shiratori O, Higaki J, Hirata M (1988) Fluorine-containing amino acids and their derivatives. 7. Synthesis and antitumor activity of α- and γ-substituted methotrexate analogs. Tetrahedron 44: 5375-5387
57. Unkeless JC, Goldman P (1970) Fluorinated γ-aminobutyric acid. Enzymatic synthesis and biological activity of a potentially useful analogue. Mol Pharmacol 6: 46-53
58. Unkeless JC, Goldman P (1971) The diastereomers of γ-fluoroglutamate: Complementary structural analogues. Mol Pharmacol 7: 293-300
59. Welch JT (1991) Selective fluorination in organic and bioorganic chemistry, 199th National Meeting of the American Chemical Society, Boston, Masachusetts, 1990, American Chemical Society, Washington, DC