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2013 | 94 | 4 |

Tytuł artykułu

Microbial biotransformation of two phosphonoacetic acid derivatives bearing two stereomeric centres

Treść / Zawartość

Warianty tytułu

Języki publikacji

EN

Abstrakty

EN
Three strains of microorganisms: Bacillus subtilis, Serratia liquefaciens and Escherichia coli were tested as whole-cell biocatalysts for the kinetic resolution of isomers of two new phosphonoacetic acid derivatives. Used compounds possess two chiral centres – one at the carbon adjacent to both functional groups and the other at the phosphorus. Biocatalytic hydrolysis of 2-butyryloxy-2-(butoxyetoxyphosphinyl)acetic acid and 2-butyryloxy-2-(isobutoxyetoxyphosphinyl) acetic acid with whole cells of Bacillus subtilis produced corresponding hydroxyphosphonates with diastereoselectivity ranging from 50 to 60%.

Wydawca

-

Rocznik

Tom

94

Numer

4

Opis fizyczny

p.425-431,fig.,ref.

Twórcy

  • Department of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Technology, Wroclaw, Poland
autor
  • Department of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Technology, Wroclaw, Poland

Bibliografia

  • Caplan N.A., Pogson Ch.I., Hayes D.J., Blackburn G.M. (2000) The synthesis of novel bisphosphonates as inhibitors ofphosphoglycerate kinase (3-PGK). J. Chem. Soc., PerkinTrans. 1: 421-437.
  • Kategaonkar A.H., Pokalwar R.U., Sonar S.S., Gawali V.U. (2010) Synthesis, in vitro antibacterial and antifungal evaluationsof new α-hydroxyphosphonate and new α-acetoxyphosphonatederivatives of tetrazolo [1, 5-a] quinoline.Eur. J. Med. Chem. 45: 1128-1132.
  • Klimek-Ochab M., Żymańczyk-Duda E., Brzezińska-Rodak M., Majewska P., Lejczak B. (2008) ETective fungal catalyzed synthesis of P-chiral organophosphorus compounds. Tetrahedron: Asymm. 19: 450-453.
  • Kolodiazhnyi O.I. (2005) Asymmetric synthesis of hydroxyphosphonates. Tetrahedron: Asymm. 16: 3295-3340.
  • Kolodiazhnyi O.I. (2012) Recent developments in the asymmetric synthesis of P-chiral phosphorus compounds. Tetrahedron: Asymm. 23: 1-46.
  • Kosolapoff G.M. (1951) Preparation of Some Mixed Dialkyl Phosphites. J. Am. Chem. Soc. 73: 4989.
  • Magee W.C., Evans D.H. (2012) The antiviral activity and mechanism of action of (S)-[3-hydroxy-2-(phosphonomethoxy) propyl] (HPMP) nucleosides. Antivir. Res. 96: 169-180.
  • Majewska P., Kafarski P., Lejczak B., Bryndal I., Lis T. (2006) An approach to the synthesis and assignment of the absolute configuration of all enantiomers of ethyl hydroxy(phenyl) methane(P-phenyl)phosphinate. Tetrahedron: Asymm.17: 2697-2701.
  • Majewska P., Kafarski P., Lejczak B. (2006) Simple and effective method for the deracemization of ethyl 1-hydroxyphosphinate using biocatalysts with lipolytic activity. Tetrahedron: Asymm. 17: 2870-2875.
  • Majewska P., Doskocz M., Lejczak B., Kafarski P. (2009) Enzymatic resolution of a–hydroxyphosphinates with two stereogenic centers and determination of absolute configuration of obtained stereoisomers. Tetrahedron: Asymm. 20: 1568-1574.
  • Malinowska B., Majewska P., Szatkowski P., Kafarski P., Lejczak B. (2011) Kinetic resolution of (±)-diethyl- and dibenzyl hydroxy(phenyl) methanephosphonates and their acyl derivatives with lipases. Biocatal. Biotrans. 29: 271-277.
  • Nesterov V.V., Kolodiazhnyi O.I. (2006) New method for the asymmetric hydroboration of ketophosphonates and the synthesis of phospho-carnitine. Tetrahedron: Asymm. 17: 1023-1026.
  • Pawar V.D., Bettigeri S., Weng S.-S., Kao J.-Q., Chen C.-T. (2006) Highly Enantioselective Aerobic Oxidation of r- Hydroxyphosphonates Catalyzed by Chiral Vanadyl(V)Methoxides Bearing N-Salicylidene-r-aminocarboxylates.J. Am. Chem. Soc. 128: 6308-6309.
  • Plażuk D., Zakrzewski J., Rybarczyk-Pirek A. (2006) Resolution and absolute configuration of dimethyl hydroxy-(ferrocenylmethyl)phosphonate. Tetrahedron: Asymm. 17:1975-1978.
  • Skwarczyński M., Lejczak B., Kafarski P. (1999) Enantioselective Hydrolysis of 1-Butyryloxyalkylphosphonates by Lipolytic Microorganisms: Pseudomonas fluorescens and Penicillium citrinum. Chirality 11: 109-114.

Typ dokumentu

Bibliografia

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