A new approach to the efficient method for the asymmetric synthesis of (S)-O-, M-, P-fluorophenylalanines and their 2-methyl-substituted analogs

Synthetic Communications

Volumn 41, Issue 4, 2011, Pages 493-506

  Saghiyan, Ashot S ^a   Petrosyan, Satenik G ^a   Manasyan, Luiza L ^a   Dadayan, Slavik A ^a   Geolchanyan, Arpine V ^a   Panosyan, Henry A ^b   Maleev, Victor I ^c   Khrustalev, Victor N ^c  

^a YEREVAN STATE UNIVERSITY   (Armenia)

^b Molecular Structure Research Center Yerevan   (Armenia)

^c A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

Asymmetric synthesis; c alkylation; chiral NiII complex; fluorophenylalanine

Indexed keywords

4 FLUOROPHENYLALANINE; ALANINE; GLYCINE; SCHIFF BASE;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; STEREOCHEMISTRY;

EID: 79551670551     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911003587531     Document Type: Article

References (19)

1. (a) Wildes, R. A.; Pitman, M. G.; Schaefer, N. Comparison of isomers of fluorophenyla-lanine as inhibitors of ion transport across barley roots. Austral. J. Plant Physiol. 1975, 2, 659-661;
2. (b) Wheatley, D. N.; Henderson, J. Y. p-Fluorophenylalanine and "division-related proteins." Nature 1974, 247, 281-283;
3. (c) Gillam, S. S.; Woo, S. L. C.; Woolf, L. I. The isolation and properties of phenylalanine hydroxylase from rat liver. Biochem. J. 1974, 139, 731-739;
4. (d) Poillon, W. N. Noncovalent inhibitors of sickle hemoglobin gelation: Effects of aryl-substituted alanines. Biochemistry 1982, 21, 1400-1406.
5. Bikshapathy, E.; Sitaram, N.; Nagaranj, R. Effect of Introducing p-fluorophenylalanine and multiple tryptophan residues in a 13-residue antibacterial peptide. Protein Peptide Lett. 1999, 6, 67-71.
6. (a) Gullbo, J.; Lindhagen, E.; Bashir-Hassan, S.; Tullberg, M.; Ehrsson, H.; Lewensohn, R.; Nygren, P.; Torre, M.; Luthman, K.; Larsson, R. Antitumor efficacy and acute toxicity of the novel dipeptide melphalanyl-p-L- fluorophenylalanine ethyl ester (J1) in vivo. Invest. New Drugs 2004, 22, 411-420;
7. (b) Gullbo, J.; Wallinder, C; Tullberg, M.; Lovborg, H.; Ehrsson, H.; Lewensohn, R.; Nygren, P.; Luthman, K.; Larsson, R. Antitumor activity of the novel melphalan containing tripeptide J3 (l-prolyl-l-melphalanyl-p-l- fluorophenylalanine ethyl ester): Comparison with its m-l-sarcolysin analogue P2. Mol. Cancer Ther. 2003, 2, 1331-1339.
8. Lourens, D. R.; Benett, P. N. Clinical Pharmacology; Medicina: Moscow, 1993.
9. Soloshonok, V. A.; Belokon, Y. N.; Kukhar, V. P.; Chernoglazova, N. I.; Saporovskaya, M. B.; Bakhmutov, V. I.; Kolycheva, M. T.; Belikov, V. M. Asymmetric synthesis of heteroorganic analogs of natural compounds: A convenient preparative method for the synthesis of enantiomerically pure (S)-(-)-o-, m-, and p-fluorophenylalanines and their 2-methylsubstituted analogs. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya 1990, 7, 1630-1636.
10. (a) Belokon, Y. N. Chiral complexes of Ni(II), Cu(II), and Cu(I) as reagents, catalysts and receptors for asymmetric synthesis and chiral recognition of amino acids. Pure Appl. Chem. 1992, 64, 1917-1924;
11. (b) Soloshonok, V. A.; Ohkura, H.; Sorochinsky, A.; Voloshin, N.; Markovsky, A.; Belik, M.; Yamazaki, T. Convenient, large-scale asymmetric synthesis of b-aryl-substituted a,a-difluoro-b-amino acids. Tetrahedron Lett. 2002, 43, 5445-5448.
12. (a) Belokon, Y. N.; Maleev, V. I.; Saporovskaya, M. B.; Bakhmutov, V. I.; Timofeeva, T. V.; Batsanov, A. S.; Struchkov, Y. T. Ni(II) complexes of Schiff s base of glycine and alanine with (S)-N-(a-naphtyl)proline derivatives for asymmetric synthesis of amino acids. Koordinats. Khim. 1988,11, 1565-1575;
13. (b) Popkov, A.; Gree, A.; Nadvorn?k, M.; Lycka. A. Chiral nucleophilic glycine and alanine synthons: Nickel (II) complexes of Schiff bases of (S)-N-(2,4,6-trimethylbenzyl)proline (2-benzoylphenyl)amide and glycine or alanine. Trans. Metal Chem. 2002, 27, 884-887;
14. (c) Belokon', Y. N.; Maleev, V. I.; Petrrosyan, A. A.; Savel'eva, T. F.; Ikonnikov, N. S.; Peregudov, A. S.; Khrustalev, V. N.; Saghiyan, A. S. Halo-substituted (S)-N-(2-benzoylphenyl)-1-benzylpyrolidine-2-carboxamides as new chiral auxiliaries for the asymmetric synthesis of (S)-a-amino acids. Russ. Chem. Bull. Int. Ed. 2002, 51, 1593-1599.
15. II complexes of Schiff s bases of glycine and alanine for efficient asymmetric synthesis of a-amino acids. Tetrahedron: Asymmetry 2006, 17, 455-467.
16. Saghiyan, A. S.; Manasyan, L. L.; Dadayan, S. A.; Petrosyan, S. G.; Petrosyan, A. A.; Maleev, V. I.; Khrustalev, V. N. Novel modified chiral Ni complexes with the Schiff bases of (E)- and (Z)-2-aminobut-2-enoic acids. Russ. Chem. Bull. Internat. Ed. 2006, 55, 442-450.
17. (a) Belokon, Y. N.; Bulychev, A.; Vitt, S.; Struchkov, Y.; Batsanov, A.; Timofeeva, T.; Tsyrypkin, V.; Ryzhov, M.; Lysova, L.; Bakhmutov, V.; Belikov, V. General method of diastereo- and enantioselective synthesis of b-hydroxy-a-amino acids by condensation of aldehydes and ketones with glycine. J. Am. Chem. Soc. 1985, 107, 4252-4259;
18. (b) Belokon, Y. N.; Saghyan, A. S.; Djamgaryan, S. M.; Bakhmutov, V. I.; Vitt, S. V.; Batsanov, A. S.; Struchkov, Y. T.; Belikov, V. M. General method of the asymmetric synthesis of anti-diastereoisomers of b-substituted L-2-aminobutanoic acids via chiral Ni(II) Schiff's base complexes of dehydroaminobutanoic acid. X-ray crystal and molecular structure of the nickel(II) complex of the Schiff's base from [(benzylprolyl)amino]benzophe-none and dehydroaminobutanoic acid. J. Chem. Soc. Perkin Trans. 1 1990, 2301-2310;
19. (c) Saghyan, A. S.; Geolchanyan, A. V.; Petrosyan, S. G.; Ghochikyan, T. V.; Haroutunyan, V. S.; Avetisyan, A. A.; Belokon, Y. N.; Fisher, F. Asymmetric synthesis of b-heterocycle substituted L-a-amino acids. Tetrahedron: Asymmetry 2004, 15, 705-711.