Synthesis of new δ-(polyfluoroalkyl)-oδ-hydroxy-α-amino acids

European Journal of Organic Chemistry

Volumn , Issue 29, 2009, Pages 5012-5019

  Tolmacheva, Nataliya A ^a   Gerus, Igor I ^a   Dolovanyuk, Violetta G ^a   Kondratov, Ivan S ^a   Haufe, Günter ^b  

^a INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

2 Pyrones; Amino acids; Fluorine; Hydrogenation; Polyfluoroalkyl groups; Ring opening

Indexed keywords

EID: 70349765817     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900684     Document Type: Article

References (19)

1. a) J.-P. Bégué, D. Bonnet-Delpon, J. Fluorine Chem. 2006,127, 992-1012;
2. b) J.-P. Bégué, D. Bonnet-Delpon, Bioorganic and Médicinal Chemistry of Fluorine, John Wiley & Sons, Inc., Hoboken, New Jersey, 2008, p. 365;
3. c) Fluorine and Health - Molecular Imaging, Biomedical Materials and Pharmaceuticals (Eds.: A. Tressaud, G. Haufe), Elsevier, Amsterdam, 2008, pp. 553-778.
4. Fluorine-Containing Amino Acids, Synthesis and Properties (Eds.: V. P. Kukhar', V. A. Soloshonok), Wiley, Chichester, 1995.
5. For some recent reviews on the synthesis of fluorinated amino acids, see: a) A. Sutherland, C. L. Willis, Nat. Prod Rep 2000, 17, 621-631;
6. b) X.-L. Oju, W-D. Meng, F.-L. Qing, Tetrahedron 2004, 60, 6711-6745;
7. c) R. Smits, C. D. Cadicamo, K. Burger, B. Koksch, Chem. Soc. Rev. 2008, 37, 1727-1739.
8. For some applications of 5-hydroxyvaleric acid for biochemical investigations, see: a) J. Pietzsch, Biochem. Biophys. Res. Commun. 2000, 270, 852-857;
9. b) H. Luesch, D. Hoffmann, J. M. Hevel, J. E. Becker, T. Golakoti, R. E. Moore, J. Org Chem. 2003, 68, 83-91.
10. 3CHNH moiety as a bioisoster for the CONH group, see: a) M. Molteni, C. Pesenti, M. Sani, A. Volonterio, M. Zanda, J. Fluorine Chem. 2004, 125, 1735-1743;
11. b) S. Bigotti, S.V. Meffle, A. Volonterio, M. Zanda, J. Fluorine Chem. 2008, 129, 767-774 and references cited therein.
12. J.-P. Bégué, D. Bonnet-Delpon, in Biomedical Frontiers of Fluorine Chemistry (Eds.: I. Ojima, J. McCarthy, J. T. Welch), ACS Symposium Series 639, ACS, Washington, DC, 1996, pp. 59-73.
13. J. P. Alexander, T. J. Ryan, D. P. Bailou, J. K. Coward, Biochemistry 2008, 47, 1228-1239.
14. T. Tsukamoto, T. Kitazume, J. J. McGuire, J. K. Coward, J. Med Chem. 1996, 39, 66-72 and references cited therein.
15. I.I. Gerus, N. A. Tolmachova, S. I. Vdovenko, R. Fröhlich, G. Haufe, Synthesis 2005, 1269-1278.
16. N. A. Tolmachova, I. I. Gerus, S. I. Vdovenko, M. Essers, R. Fröhlich, G. Haufe, Eur. J. Org Chem. 2006, 4704-4709.
17. A. P. Nin, R. M. de Lederkremer, O. Varela, Tetrahedron 1996, 52, 12911-12918.
18. J. Weiss, T. Weiss, Handbook of Ion Chromatography, 3rd ed., Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2004.
19. G. M. Sheldrick, SHELXTL PLUS, PC version, A system of computer programs for the determination of crystal structure from X-ray diffraction data, Rev. 5.1., 1998.