Direct enzymatic route for the preparation of novel enantiomerically enriched hydroxylated β-amino ester stereoisomers

Molecules

Volumn 15, Issue 6, 2010, Pages 3998-4010

  Forró, Eniko ^a   Schönstein, László ^a   Kiss, Loránd ^a   Vega Peñaloza, Alberto ^b   Juaristi, Eusebio ^b   Fülöp, Ferenc ^a,c  

^a UNIVERSITY OF SZEGED   (Hungary)

^b DEPARTAMENTO DE FÍSICA   (Mexico)

^c UNIVERSITY OF SZEGED   (Hungary)

Author keywords

Amino ester; Enantioselective; Enzyme; Hydrolysis; Hydroxylation; Organic solvent; Stereoisomer

Indexed keywords

AMINO ACID; ESTER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS, CYCLIC; ESTERS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77954305251     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15063998     Document Type: Article

References (34)

1. Fülöp, F. The chemistry of 2-aminocycloalkanecarboxylic acids. Chem. Rev. 2001, 101, 2181-2204.
2. Kiss, L.; Forró, E.; Fülöp, F. Amino Acids, Peptides and Proteins in Organic Chemistry; Hughes, A. B., Ed.; Wiley-VCH: Weinheim, Germany, 2009; Volume 1, pp. 367-409.
3. Zegarac, M.; Mestrovic, E.; Hulita, N. K.; Filic, D.; Dumic, M.; Grunenberg, A.; Keil, B.; Ceric, H. Solid state forms of (-)-(1R, 2S)-2-amino-4-methylenecyclopentanecarboxylic acid. PCT Int. Appl. WO 2005100302 A1, 2005.
4. Hameršak, Z.; Roje, M.; Avdagić, A.; Šunjić, V. Quinine-mediated parallel kinetic resolution of racemic cyclic anhydride: Stereoselective synthesis, relative and absolute configuration of novel alicyclic β-amino acids. Tetrahedron Asymmetr. 2007, 18, 635-644.
5. Steer, D. L.; Lew, R. A.; Perlmutter, P.; Smith, A. I.; Aguilar, M. I. β-Amino Acids. Versatile peptidomimetics. Curr. Med. Chem. 2002, 9, 811-822.
6. Martinek, T. A.; Mándity, I. M.; Fülöp, L.; Tóth, G. K.; Vass, E.; Hollósi, M.; Forró, E.; Fülöp, F. Effects of the alternating backbone configuration on the secondary structure and self-assembly of β-peptides. J. Am. Chem. Soc. 2006, 128, 13539-13544.
7. Price, J. L.; Horne, W. S.; Gellman, S. H. Discrete heterogeneous quaternary structure formed by./β-peptide foldamers and.-peptides. J. Am. Chem. Soc. 2007, 129, 6376-6377.
8. Mándity, I. M.; Wéber, E.; Martinek, T. A.; Olajos, G.; Tóth, G. K.; Vass, E.; Fülöp, F. Design of peptidic foldamer helices: A stereochemical patterning approach. Angew. Chem. Int. Ed. 2009, 48, 2171-2175.
9. Fernández, D.; Torres, E.; Avilés, F. X.; Ortuòo, R. M.; Vendrell, J. Cyclobutane-containing peptides: Evaluation as novel metallocarboxypeptidase inhibitors and modelling of their mode of action. Bioorg. Med. Chem. 2009, 17, 3824-3828.
10. Kapferer, P.; Vasella, A. Electrophilic bromination of N-acylated cyclohex-3-en-1-amines: Synthesis of 7-azanorbornanes. Helv. Chim. Acta 2004, 87, 2764-2789.
11. Carter, P. H. Process for preparation of diprotected 3-(4-fluorobenzyl)- 1-(2, 5-diaminocyclohexyl) piperidine via reductive amination. U. S. Pat. Appl. 2005/277, 666, 2005;
12. [Chem. Abstr. 2005, 144, 51452].
13. Fülöp, F.; Miklós, F.; Forró, E. Diexo-3-aminonorbornane-2-carboxylic acid as highly applicable chiral source for the enantioselective synthesis of heterocycles. Synlett 2008, 1687-1689.
14. Kiss, L.; Nonn, M.; Forró, E.; Sillanpää, R.; Fülöp, F. Synthesis of novel isoxazoline-fused cispentacin stereoisomers. Tetrahedron Lett. 2009, 50, 2605-2608.
15. Gedey, S.; Van der Eycken, J.; Fülöp, F. Synthesis of alicyclic β-lactams via the Ugi reaction on a solid support. Lett. Org. Chem. 2004, 1, 215-217.
16. Kanizsai, I.; Gyónfalvi, S.; Szakonyi Z.; Sillanpää, R.; Fülöp, F. Synthesis of bi-and tricyclic β-lactam libraries in aqueous medium. Green Chem. 2007, 9, 357-360.
17. Kiss, L.; Forró, E.; Sillanpää, R.; Fülöp, F. Diastereo-and enantioselective synthesis of orthogonally protected 2, 4-diaminocyclopentanecarboxylates: a flip from β-amino-to β, γ diaminocarboxylates. J. Org. Chem. 2007, 72, 8786-8790.
18. Juaristi, E.; Soloshonok, V. A. Enantioselective synthesis of β-amino acids, 2nd ed.; Wiley-Interscience: New York, NY, USA, 2005.
19. Mowery, B. P.; Lee, S. E.; Kissounko, D. A.; Epand, R. F.; Epand, R. M.; Weisblum, B.; Stahl, S. S.; Gellman, S. H. Mimicry of antimicrobial host-defense peptides by random copolymers. J. Am. Chem. Soc. 2007, 129, 15474-15476.
20. Juaristi, E.; Lopez-Ruiz, H. Recent advances in the enantioselective synthesis of beta-amino acids. Med. Chem. 1999, 6, 983-1004.
21. Palkó, M.; Kiss, L.; Fülöp, F. Syntheses of hydroxylated cyclic β-amino acids and derivatives. Curr. Med. Chem. 2005, 12, 3063-3083.
22. Kingston D. G. I.; Newman D. J. Taxoids: Cancer-fighting compounds from nature. Curr. Opin. Drug Disc. Dev. 2007, 10, 130-144.
23. Bunnage, M. E.; Ganesh, T.; Masesane, I. B.; Orton, D.; Steel, P. G. Asymmetric Synthesis of the Putative Structure of (-)-Oryzoxymycin. Org. Lett. 2003, 5, 239-242.
24. Ichikawa, Y.; Ohbayashi, M.; Hirata, K.; Nishizawa, R.; Isobe, M. Synthesis of Blastidic acid and Cytosinine, two components of Blasticidin S. Synlett 2001, 1763-1766.
25. Kiss, L.; Forró, E.; Fülöp, F. A new strategy for the regio-and stereoselective hydroxylation of trans-2-aminocyclohexenecarboxylic acid. Tetrahedron Lett. 2006, 47, 2855-2858.
26. Kiss, L.; Forró, E.; Sillanpää, R.; Fülöp, F. Novel functionalized cispentacin derivatives. Synthesis of 1, 2, 3-triazole-substituted 2-aminocyclopentanecarboxylate stereoisomers. Tetrahedron Asymmetr. 2008, 19, 2856-2860.
27. Benedek, G.; Palkó, M.; Wéber; E.; Martinek, T. A.; Forró, E.; Fülöp, F. Efficient synthesis of 3, 4-and 4, 5-dihydroxy-2-aminocyclohexanecarboxylic acid enantiomers. Tetrahedron Asymmetr. 2009, 20, 2220-2225.
28. Kiss, L.; Fulop, F. Selective Syntheses of Functionalized Cyclic β-Amino Acids via Transformation of the Ring C-C Double Bonds. Synlett 2010, 1302-1314.
29. Forro E.; Fulop F. The first direct enzymatic hydrolysis of alicyclic β-amino esters:-a route to enantiopure cis and trans β-amino acids. Chem. Eur. J. 2007, 13, 6397-6401.
30. Tasnadi G.; Forro E.; Fulop F. An efficient new enzymatic method for the preparation of β-aryl-β-amino acid enantiomers. Tetrahedron Asymmetr. 2008, 19, 2072-2077.
31. Tasnadi G.; Forro E.; Fulop F. Burkholderia cepacia lipase is an excellent enzyme for the enantioselective hydrolysis of β-heteroaryl- β-amino esters. Tetrahedron Asymmetr. 2009, 15, 1771-1777.
32. Tasnadi G.; Forro E.; Fulop F. An improved enzymatic method for the preparation of valuable β-arylalkyl-substituted β-amino acid enantiomers. Org. Biomol. Chem. 2010, 8, 886-895.
33. Fulop, F.; Palko, M.; Forro, E.; Dervarics, M.; Martinek, T. A.; Sillanpaa, R. Facile regio-and diastereoselective syntheses of hydroxylated 2-aminocyclohexanecarboxylic acids. Eur. J. Org. Chem. 2005, 3214-3220.
34. Forro, E. New gas chromatographic method for the enantioseparation of β-amino acids by a quick double-derivatization technique. J. Chromatogr. A 2009, 1216, 1025-1029.