Syntheses of fluorinated amino acids: From the classical to the modern concept

Amino Acids

Volumn 11, Issue 1, 1996, Pages 15-36

  Tolman, V ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

Amino acids; Fluoro analogues; Synthesis

Indexed keywords

AMINO ACID; AMINO ACID DERIVATIVE; HYDANTOIN;

ALKYLATION; AMINO ACID SYNTHESIS; ARTICLE; FLUORINATION; PRIORITY JOURNAL;

EID: 0029775909     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF00805718     Document Type: Article

References (89)

1. 18F]6-fluorodopa with fluorine-18 acetylhypofluorite. J Nucl Med 27: 1462-1466
2. Bennett EL, Niemann C (1950) Preparation and resolution of the three isomeric nuclear substituted monofluoro-DL-phenylalanines. J Am Chem Soc 72: 1800-1803
3. Bergmann ED, Chun-Hsu L (1973) Organic fluorine compounds. XLVI. γ-Fluoroglutamic acid and fluorofolic acid. Synthesis: 44-46
4. Bey P, Schirlin D (1978) General approach to the synthesis of α-difluoromethylamines as potential enzyme-activated irreversible inhibitors. Tetrahedron Lett: 5225-5228
5. Bey P, Vevert JP (1978) New approach to the synthesis of α-halogenomethyl-α-amino acids. Tetrahedron Lett: 1215-1218
6. Bey P, Vevert JP, Van Dorsselaer V, Kolb M (1979) Direct synthesis of α-haloaenomethyl-α-amino acids from the parent α-amino acids. J Org Chem 44: 2732-2742
7. Bey P, Ducep JB, Schirlin D (1984) Alkylation of malonates or Schiff base anions with dichlorofluoromethane as a route to α-chlorofluoromethyl or α-fluoromethyl α-amino acids. Tetrahedron Lett 25: 5657-5660
8. Blažvić N, Zymalkowski F (1975) Stereoselective synthesses of diastereomeric DL-3-(p-fluorophenyl) serines and -isoserines. Arch Pharm 308: 541-9
9. 18F-Fluoroalkylation of H-acidic compounds. J Labelled Comp Radiopharm 25: 201-216
10. Brace NO (1967) α-Aminoalkanoic and alkenoic acids with perfluoroalkyl terminal segments. J Org Chem 32: 430-434
11. Cavalleri B, Bellasio E, Testa E (1966a) Fluorinated organic compounds with potential biological activity. I. Fluorinated derivatives of pimelic acid. Gazz Chim Ital 96: 227-252
12. Cavalleri B, Bellasio E, Testa E (1966b) Findings on fluorinated organic compounds with potential biological activity. II. Fluorinated derivatives of α-amino and α,α′-diaminopimelic acids. Gazz Chim Ital 96: 253-263
13. Chirakal R, Brown KL, Firnau G, Garnett ES, Hughes DW, Sayer BG, Smith RW (1987) Synthesis of 2- and 3-fluorotyrosine with dilute fluorine gas. J Fluorine Chem 37: 267-278
14. Christensen HN, Oxender DL (1963) The acid strength of the amino group as a factor in the transport of amino acids. Biochem Biophys Acta 74: 386-391
15. 18F]fluorophenylalanines for probing protein synthesis. Nuclearmedizin [Suppl] 22: 600-602
16. Curtley PE, Hirschmann RF (1983) Fluorinated cyclic hexapeptide somatostatin analogs. US Pat 4 427 611; Chem Abstr (1984) 100: 192286a
17. Curtley PE, Hirschmann RF (1983) Fluorinated cyclic hexapeptide somatostatin analogs. US Pat 4 427 611; Chem Abstr (1984) 100: 192286a
18. Dannley RL, Taborsky RG (1957) Synthesis of DL-S-trifluoromethylhomocysteine (trifluoromethylmethionine). J Org Chem 22: 1275-1276
19. Dolling VH, Douglas AW, Grabowski EJJ, Schoenewaldt EF, Sohar P, Sletzinger M (1978) Synthesis and resolution of 3-fluoro-DL-alanine-2-d A selective deuteration via reductive amination with sodium borodeuteride. J Org Chem 43: 1634-1640
20. Filler R, Novar H (1960) Fluorinated aromatic amino acids. I. o-,m- and p-Trifluoromethylphenylalanines. J Org Chem 25: 733-736
21. Filler R, Ayyangar NR, Gustowski W, Kang HH (1969) New reactions of polyfluoroaromatic compounds. Pentafluorophenylalanine and tetrafluorotyrosine. J Org Chem 34: 534-538
22. Firnau G, Chirakal R, Sood S, Garnett ES (1980) Aromatic fluorination with xenon difluoride: L-3,4-dihydroxy-6-fluorophenylalanine. Can J Chem 58: 1449-1450
23. 18F]fluoro-L-dopa. J Nucl Med 25: 1228-1233
24. 2 in anhydrous hydrogen fluoride. J Labelled Comp Radiopharm 23: 1106-1110
25. Garrett GS, Emge TJ, Lee SC, Fisher EM, Dyehouse K, McIver JM (1991) Synthesis of the monofluoro ketone peptide isosters. J Org Chem 56: 4823-4826
26. Gershon H, McNeil MW, Bergmann ED (1973) Amino acid analogs. II. 3-Fluoroamino acids. I. Chain length three to seven carbon atoms. J Med Chem 16: 1407-1409
27. Hagemann JJM, Wanner MJ, Koomen GJ, Pandit UK (1977) Potential carcinostatics. Synthesis and biological properties of d- and 1-β,β-difluoroaspartic acid and β,β-difluoroasparagine. J Med Chem 20: 1677-1679
28. Hanuš J, Tolman V, Vereš K (1973) Synthesis of 2,6-diaminopimelic acid and its 4-substituted derivatives. Coll Czech Chem Commun 38: 1212
29. Hebel D, Kirk KL, Cohen LA, Labroo VM (1990) First direct fluorination of tyrosine-containing biologically active peptides. Tetrahedron Lett 31: 619-622
30. Heinzer F, Martin P (1981) Eine neue Synthese von DL-Armentomycin und verwandten 2-Amino-4-Polyhalogenobuttersäuren. Helv Chim Acta 64: 1379-1386
31. Hoshi H, Aburaki S, Imura S, Yamasaki T, Naito T, Kawaguchi H (1990) Amikacin analogs with a fluorinated amino acid side chain. J Antibiotics 43: 858-872
32. Houston ME jr, Honek JF (1989) Facile synthesis of fluorinated methionines. J Chem Soc Chem Commun: 761-762
33. Hudlický M (1960) Synthesis of γ-fluoroglutamic acid. Tetrahedron Lett: 21-24
34. Hudlický M (1961) Organic compounds of fluorine. II. Fluorinated amino acids. Collect Czech Chem Commun 26: 1414-1421
35. Hudlický M (1993) Stereospecific syntheses of all four stereoisomers of 4-fluoroglutamic acid. J Fluorine Chem 60: 193-210
36. Hudlický M, Merola JS (1990) New stereospecific syntheses and X-ray diffraction structures of (-)-D-erythro- and (+)-L-threo-4-fluoroglutamic acid. Tetrahedron Lett 31: 7403-7406
37. Jansen AF, Wang PMC, Lemire AE (1983) Fluorination of methionine and methionylglycine derivatives with xenon difluoride. J Fluorine Chem 22: 557-559
38. Kamandi E, Frahm AW, Zymalkowski F (1975) Synthesis of β-phenylisoserines by ammonolysis of β-phenylglycidates. II. Arch Pharm 308: 135-141
39. Kollonitsch J (1977) Substitutive fluorination of organic compounds. US Pat 4 030 994: Chem Abstr (1977) 87: 83904t
40. Kollonitsch J (1977) Substitutive fluorination of organic compounds. US Pat 4 030 994: Chem Abstr (1977) 87: 83904t
41. Kollonitsch J, Barash L, Douldoras GA (1970) Photofluorination with fluoroxytrifluoromethane, a general method for the synthesis of organic fluorine compounds. Direct fluorination of bioactive molecules. J Am Chem Soc 92: 7494-7495
42. Kollonitsch J, Marburg S, Perkins LM (1975) Selective fluorination of hydroxy amines and hydroxy amino acids with sulfur tetrafluoride in liquid hydrogen fluoride. J Org Chem 40: 3808-3809
43. Kollonitsch J, Barash L (1976) Organofluorine syntheses via photofluorination: 3-fluoro-D-alanine and 2-deutero analogue, antibacterials related to the bacterial cell wall. J Am Chem Soc 98: 5591-5593
44. Kollonitsch J, Marburg S, Perkins LM (1976) Fluorodesulfurization. A new reaction for the formation of carbon-fluorine bonds. J Org Chem 41: 3107-3111
45. Kollonitsch J, Marburg S, Perkins LM (1979) Fluorodehydroxylation, a novel method for synthesis of fluoroamines and fluoroamino acids. J Org Chem 44: 771-777
46. Kuo D, Rando RR (1981) Irreversible inhibition of Glutamate decarboxylase by α-(fluoromethyl)glutamic acid. Biochemistry 20: 506-511
47. Lazar J, Sheppard WA (1968) Fluorinated analogs of leucine, methionine, and valine. J Med Chem 11: 138-140
48. Lettré H, Wölcke U (1967) Fluor-Derivate biogener aliphatischer Aminosäuren. Justus Liebigs Ann Chem 708: 75-85
49. Loncrini DF, Walborsky HM (1964) The synthesis of 2-amino-3-trifluoromethylbutyric acid. J Med Chem 7: 369
50. Lontz JF, Raasch MS (1953) α-Amino-α-fluoroalkyl or cycloalkyl carboxylic acids. US Pat 2 662 915; Chem Abstr (1954) 48: 12795a
51. Lontz JF, Raasch MS (1953) α-Amino-α-fluoroalkyl or cycloalkyl carboxylic acids. US Pat 2 662 915; Chem Abstr (1954) 48: 12795a
52. Luxen A, Barrio JR, Bida GT, Satyamurthy N (1986) Regioselective radiofluorodemercuration. A simple, high yield synthesis of 6-[F-18]fluorodopa. J Labelled Comp Radiopharm 23: 1066-1067
53. Luxen A, Barrio JR (1988) Fluorination of substituted veratroles via regioselective mercuration. Tetrahedron Lett 29: 1501-1504
54. Maki Y, Inukai K (1976) Synthesis of fluorine-containing DL-alanine derivatives. J Synth Org Chem Jpn 34: 722-725: Chem Abstr (1977) 87: 68600x
55. Maki Y, Inukai K (1976) Synthesis of fluorine-containing DL-alanine derivatives. J Synth Org Chem Jpn 34: 722-725: Chem Abstr (1977) 87: 68600x
56. Muller N (1987) Synthesis of 5,5,5-trifluoro-DL-isoleucine and 5,5,5-trifluoro-DL-alloisoleucine. J Fluorine Chem 36: 163-170
57. Ojima I, Hirai K, Fujita M, Fuchikami T (1985) New synthetic route to N-acyl α-amino acids via amidocarbonylation by means of homogenous binary catalyst systems. J Organomet Chem 279: 203-214
58. Ojima I, Kato K, Nakahashi K, Fuchikami T, Fujita M (1989) New and effective routes to fluoro analogues of aliphatic and aromatic amino acids. J Org Chem 54: 4511-4522
59. Prudchenko AT (1970) Fluorinated phenylalanines. Izv Sib Otd Akad Nauk SSSR, Ser Khim Nauk 14: 95-100; Chem Abstr (1971) 75: 6265k
60. Prudchenko AT (1970) Fluorinated phenylalanines. Izv Sib Otd Akad Nauk SSSR, Ser Khim Nauk 14: 95-100; Chem Abstr (1971) 75: 6265k
61. Raasch MS (1958) 5-Fluoronorvaline and 6-fluoronorleucine. J Org Chem 23: 1567-1568
62. Reider PJ, Conn RSE, Davis P, Grenda VJ, Zambito AJ, Grabowski EJJ (1987) Synthesis of (R)-serine-2-d and its conversion to the broad spectrum antibiotic Fludalanine. J Org Chem 52: 3326-3334
63. Rennert OM, Anker HS (1963) On the incorporation of 5,5,5-trifluoroleucine into proteins of E. coli. Biochemistry 2: 471-476
64. Sagami Chem Res Ctr (1981a) 2-Trifluoromethylpropanal. Jpn Kokai 81,161,340; Chem Abstr (1982) 96: 180787a
65. Sagami Chem Res Ctr (1981a) 2-Trifluoromethylpropanal. Jpn Kokai 81,161,340; Chem Abstr (1982) 96: 180787a
66. Sagami Chem Res Ctr (1981b) Trifluoromethylvaline. Jpn Kokai 81,164,151; Chem Abstr (1982) 96: 181623f
67. Sagami Chem Res Ctr (1981b) Trifluoromethylvaline. Jpn Kokai 81,164,151; Chem Abstr (1982) 96: 181623f
68. Schiemann G, Roselius W (1932) Über aromatische Fluorverbindungen. XII. [Fluorophenyl]-alanin. Chem Ber 65: 1439-1442
69. Schiemann G, Winkelmüller W (1932) Über ein erstes Fluortyrosin und Fluorthyronin, sowie kernfluorierte β-Phenyl-äthylamine. III. Mitteilung über fluorierte Aminosäuren und ihre Abkömmlinge. J Prakt Chem 135: 101-127
70. Schirlin D, Ducep JB, Baltzer S, Bey P, Piriou F, Wagner J, Hornsperger JM, Heydt JG, Jung MJ, Danzin C, Weiss R, Fischer J, Mitschier A, De Cian A (1992) Synthesis and inhibitory properties of α-(chlorofluoromethyl)-α-amino acids, a novel class of irreversible inactivators of decarboxylases. J Chem Soc Perkin Trans I: 1053-1064
71. Sewald N, Burger K (1995) Synthesis of β-fluorine-containing amino acids. In: Kukhar' VP, Soloshonok VA (eds) Fluorine-containing amino acids. Synthesis and properties. Wiley & Sons, Chichester, pp 163-171 and 188-200
72. Shirota FN, Nagasawa HT, Elberling JA (1977) Potential inhibitors of collagen biosynthesis. 5,5-Difluoro-DL-lysine and 5,5-dimethyl-DL-lysine and their activation by lysyl-tRNA ligase. J Med Chem 20: 1623-1627
73. Shishkin GV, Mamaev VP (1965) Synthesis of β-(pentafluorophenyl)alanine. Izv Akad Nauk SSSR, Ser Khim: 934; Chem Abstr (1965) 63: 5734g
74. Shishkin GV, Mamaev VP (1965) Synthesis of β-(pentafluorophenyl)alanine. Izv Akad Nauk SSSR, Ser Khim: 934; Chem Abstr (1965) 63: 5734g
75. Shishkin GV, Mamaev VP (1966) Synthesis of β-pentafluorophenylalanine. Zh Obsch Khim 36: 660-664; Chem Abstr (1966) 65: 9010h
76. Shishkin GV, Mamaev VP (1966) Synthesis of β-pentafluorophenylalanine. Zh Obsch Khim 36: 660-664; Chem Abstr (1966) 65: 9010h
77. Soloshonok VA, Kukhar' VP, Pustovit Y, Nazaretian V (1992) A new and convenient synthesis of S-trifluoromethyl-containing amino acids. Synlett: 657-658
78. Taguchi T, Tomizawa G, Nakajima M, Kobayashi Y (1985) 1-Phenylsulphonyl-3,3,3-trifluoropropene. I. The Michael-type addition reaction. Chem Pharm Bull 33: 4077-4080
79. Tolman V, Vereš K (1967) Synthesis of certain monofluorinated aliphatic amino acids. Collect Czech Chem Commun 32: 4460-4469
80. Tolman V, Beneš J (1976) Monofluorinated analogues of some aliphatic basic amino acids. J Fluorine Chem 7: 397-407
81. Tsushima T, Nishikawa J, Sato T, Tanida H, Tori K, Tsuji T, Misaki S, Suefuji M (1980) Stereoselective synthesis of eryrthro-3-fluorophenylalanine. Tetrahedron Lett 21: 3593-3594
82. Tsushima T, Kawada K, Nishikawa J, Sato T, Tori K, Tsuji T (1984) Fluorine-containing amino acids and their derivatives. III. Stereoselective synthesis and unusual conformation features of threo- and erythro-3-fluorophenylalanine. J Org Chem 49: 1163-1169
83. Tsushima T, Kawada K, Shiratori O, Uchida N (1985) Fluorine-containing amino acids and their derivatives. V. Synthesis of novel fluorinated analogues of the antitumor agent, methotrexate. Heterocycles 23: 45-49
84. Tsushima T, Kawada K (1988) Fluorine-containing amino acids and their derivatives. VI. An efficient synthesis of β-fluorinated alanines via fluorohalomethylation of aminomalonates. Tetrahedron Lett 26: 2445-2448
85. Tsushima T, Kawada K, Ishihara S, Uchida N, Shiratori O, Higaki J, Hirata M (1988) Fluorine-containing amino acids and their derivatives. VII. Synthesis and antitumor activity of α- and β-substituted methotrexate analogs. Tetrahedron 44: 5375-5387
86. Tsushima T, Ishihara S, Fujita Y (1990) Fluorine-containing amino acids and their derivatives. IX. Synthesis and biological activities of difluoromethylhomocysteine. Tetrahedron Lett 31: 3017-3018
87. Walborsky HM, Baum ME, Loncrini DF (1955) The syntheses of ω-trifluoromethyl amino acids. II. Their microbiological activities. J Am Chem Soc 77: 3637-3640
88. Walborsky HM, Baum ME (1956) Chemical effects of the trifluoromethyl group. III. Synthesis of 2-amino-4,4,4-trifluorobutyric acid. J Org Chem 21: 538-539
89. Walborsky HM, Baum ME (1958) Chemical effects of the trifluoromethyl group. V. Reactions of ethyl β-trifluoromethylglycidate; the synthesis of 2-amino-3-hydroxy-4,4,4-trifluorobutyric acid. J Am Chem Soc 80: 187-192