Junho 2015 vol. 1 num. 3 - Congresso Brasileiro de Engenharia Química em Iniciação Científica

Artigo Completo - Open Access.

Idioma principal

PRODUÇÃO DE COMPOSTOS a-HIDROXIFOSFONATOS OPTICAMENTE ATIVOS UTILIZANDO CÉLULAS ÍNTEGRAS DE MICRORGANISMOS

SATO, L. M. ; KITAMURA, T. N. ; FARDELONE, L. C. ; RODRIGUES, J. A. R. ; MORAN, P. J. S. ;

Artigo Completo:

As reduções enantiosseletivas dos cetofosfonatos 1a-c por Lactobacillus brevis CCT 3745 forneceram (S)-(-)-((4-clorofenil)(hidroxi)metil) fosfonato de dimetila (S)-(-)-2a, (S)-(-)-((4-metoxifenil)(hidroxi)metil)fosfonato de dimetila (S)-(-)-2b, (S)-(-)-((3,4-dimetoxifenil)(hidroxi)metil)fosfonato de dimetila (S)-(-)-2c e com o uso de Candida albicans CCT 5847 forneceram (R)-(+)-((4-clorofenil)(hidroxi)metil)fosfonato de dimetila (R)-(+)-2a, (R)-(+)-((4-metoxifenil) (hidroxi)metil) fosfonato de dimetila (R)-(+)-2b e (R)-(+)-((3,4-dimetoxifenil) (hidroxi)metil)fosfonato de dimetila (R)-(+)-2c com rendimentos entre 78-90%. Os (S)-(-)- e (R)-(+)-a-hidroxifosfonatos 2a-c são importantes intermediários para síntese de produtos de química fina, agroquímicos e fármacos.

Artigo Completo:

Download (PDF)

Palavras-chave: ,

Palavras-chave: ,

DOI: 10.5151/chemeng-cobeqic2015-369-33978-263717

Referências bibliográficas
  • [1] ALEIXO L. M.; CARVALHO, M.; MORAN, P. J. S. AND RODRIGUES, J. A. R.. Hidride transfer versus electron transfer in the Baker''s yeast reduction of -haloacetophenones. Bioorganic Andamp; Medicinal Chemistry Letters, v. 3, p. 1637-1642, 1993.
  • [2] ALEGRE-REQUENA, J. V., MARQUÉS-LÓPEZ, E., MIGUEL, P. J. S., HERRERA, R. P.. Organocatalytic enantioselective hydrophosphonylation of aldehydes. Org. Biomol. Chem., v. 12, p. 1258-1264, 2014.
  • [3] BARRON, L. D.. Molecular light scattering and optical activity. Cambridge University Press, 2a edição, 2009.
  • [4] BRZEZIŃSKA-RODAK, M., KLIMEK-OCHAB, M.; ŻYMAŃCZYK-DUDA, E.; KAFARSKI, P.. Biocatalytic resolution of enantiomeric mixtures of 1-aminoethanephosphonic acid. Molecules, v. 16, p. 5896-5904, 2011.
  • [5] CAZETTA, T.; MORAN, P. J. S.; RODRIGUES, J. A. R.. Highly enantioselective deracemization of 1-phenyl-1,2-ethanediol and its derivatives by stereoinversion using Candida albicans in a one-pot process. J. Mol. Cat. B: Enzymatic, v. 109, p. 178-183, 2014.
  • [6] DAKE, S. A.; RAUT, D. S.; KHARAT, K.R.; MHASKE, R. S.; DESHMUKH, S. U.; PAWAR, R. P.. Ionic liquid promoted synthesis, antibacterial and in vitro antiproliferative activity of novel α-aminophosphonate derivatives. Bioorg. Med. Chem. Lett., v. 21, p. 2527-2532, 2011.
  • [7] DEMMER, C. S.; KROGSGAARD-LARSEN, N.; BUNCH, L.. Review on Modern Advances of Chemical Methods for the Introduction of a Phosphonic Acid Group. Chem. Rev., v. 111, p. 7981-8006, 2011.
  • [8] FARDELONE, L. C.; RODRIGUES, J. A. R.; MORAN, P. J. S.. Chiral Pharmaceutical Intermediaries Obtained by Reduction of 2-Halo-1-(4-substituted phenyl)-ethanones Mediated by Geotrichum candidum CCT 1205 and Rhodotorula glutinis CCT 2182. Enzyme Res., 2011:976368, 2011.
  • [9] GREMBECKA, J.; MUCHA, A.; CIERPICKI, T.; KAFARSKI, P.. The most potente organophosphorus inhibitors of leucine aminopeptidase. Structure-based design, chemistry, and activity. J. Med. Chem., v. 46, p. 2641-2655, 2003.
  • [10] KAFARSKI, P.; LEJCZAK., B.. Application of bacteria and fungi as biocatalysts for the preparation of optically active hydroxyphosphonates. J. Mol.Catal. B: Enzym., v. 29, p. 99-104, 2004.
  • [11] KRAICHEVA, I.; BOGOMILOVA, A.; TSACHEVA, I.; MOMEKOV, G.; TROEV, K.. Synthesis, NMR charakterysation and in vitro antitumor evaluation of new aminophosphonic acid diesters. Eur. J. Med. Chem., p. 44, p. 3363-3367, 2009.
  • [12] KROUTIL, W.; MANG, H.; KLAUS, E. FABER, K. KROUTIL, W.; MANG, H.; KLAUS, E. FABER, K.. Recent advances in the biocatalytic reduction and oxidation of sec-alcohol. Cur. Op. Chem. Biol., v. 8, p. 120-126, 2004.
  • [13] LIN SUN, L.; GUO, Q.-P.; LI, X.; ZHANG, L.; LI, Y.-Y.; DA, C.-S.. C2-Symmetric homobimetallic zinc complexes as chiral catalysts for the highly enantioselective hydrophosphonylation of aldehydes. Asian J. Org. Chem., v. 2, p. 1031-1035, 20
  • [14] MAJEWSKA, P.; KAFARSKI, P.; LEJCZAK, B.. Lipase-catalysed resolution of 1-hydroxyethane-P- phenylphosphinates. Pol. J. Chem., v. 79, p. 561-566, 2005.
  • [15] MOORE, J. D.; FINNEY, N. S.. A Simple and advantageous protocol for the oxidation of alcohols with o-iodoxybenzoic acid (IBX). Org. Lett., v. 4, p. 3001-3004, 2002.
  • [16] MOORE, M. L; DREYER, G. B.. Substrate-based inhibitors of HIV-1 protease. Perspect. Drug Discovery Des., v. 1, p. 85-108, 1993.
  • [17] OLSZEWSKI, T. K.. Asymmetric synthesis of a-hydroxymethylphosphonates and phosphonic acids via hydrophosphonylation of aldehydes with chiral H-phosphonate. Tetrahedron: Asymmetry, v. 26, p 393-399, 2015.
  • [18] RODRIGUES, J. A. R.; MORAN, P. J. S.; CONCEIÇÃO, G. J. A.; FARDELONE, L. C.. Recent advances in the biocatalytic asymmetric reductions of acetophenones and ,-unsuturated carbonyl compounds. Food. Technol. Biotechnol., v. 42, p. 295-303, 2004.
  • [19] VAHDAT, S. M.; BAHARFAR, R.; TAJBAKHSH, M.; HEYDARI, A.; BAGBANIAN, S. M.; KHAKSAR, S.. Organocatalytic synthesis of α-hydroxy and α-aminophosphonates. Tetrahedron Lett., v. 49, p. 6501-6504, 2008.
Como citar:

SATO, L. M.; KITAMURA, T. N.; FARDELONE, L. C.; RODRIGUES, J. A. R.; MORAN, P. J. S.; "PRODUÇÃO DE COMPOSTOS a-HIDROXIFOSFONATOS OPTICAMENTE ATIVOS UTILIZANDO CÉLULAS ÍNTEGRAS DE MICRORGANISMOS", p. 1059-1064 . In: Anais do XI Congresso Brasileiro de Engenharia Química em Iniciação Científica [=Blucher Chemical Engineering Proceedings, v. 1, n.3]. ISSN Impresso: 2446-8711. São Paulo: Blucher, 2015.
ISSN 2359-1757, DOI 10.5151/chemeng-cobeqic2015-369-33978-263717

últimos 30 dias | último ano | desde a publicação


downloads


visualizações


indexações