RT journal article
T1 Study of the role played by NfsA, NfsB nitroreductase and NemA flavin reductase from Escherichia coli in the conversion of ethyl 2-(2′-nitrophenoxy)acetate to 4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one (D-DIBOA), a benzohydroxamic acid with interesting biological properties
A1 Le Borgne, Sylvie
A1 Valle Gallardo, Antonio
A1 Bolívar Pérez, Jorge
A1 Cabrera Revuelta, Gema
A1 Cantero Moreno, Domingo
A2 Bioquímica y Biología MolecularMicrobiología, Medicina Preventiva, Salud Pública
A2 Ingeniería Química y Tecnología de Alimentos
K1 Biotransformation
K1 Escherichia coli
K1 Benzohydroxamic acids
K1 Nitroreductases NfsA and NfsB
K1 Flavin reductase NemA
K1 D-DIBOA
AB Benzohydroxamic acids, such as 4-hydroxy-(2H)- 1,4-benzoxazin-3(4H)-one (D-DIBOA), exhibit interesting herbicidal, fungicidal and bactericidal properties. Recently, the chemical synthesis of D-DIBOA has been simplified to only two steps. In a previous paper, we demonstrated that the second step could be replaced by a biotransformation using Escherichia coli to reduce the nitro group of the precursor, ethyl 2-(2′-nitrophenoxy)acetate and obtain D-DIBOA. TheNfsA and NfsB nitroreductases and the NemA xenobiotic reductase of E. coli have the capacity to reduce one or twonitro groups from a wide variety of nitroaromatic compounds, which are similar to the precursor. By this reason, we hypothesised that these three enzymes could be involved in this biotransformation. We have analysed the biotransformation yield (BY) of mutant strains in which one, two or three of these genes were knocked out, showing that only in the double nfsA/nfsB and in the triple nfsA/nfsB/nemA mutants, the BY was 0%. These results suggested that NfsA and NfsB are responsible for the biotransformation in the tested conditions. To confirm this, the nfsA and nfsB open reading frames were cloned into the pBAD expression vector and transformed into the nfsA and nfsB single mutants, respectively. In both cases, the biotransformation capacity of the strains was recovered (6.09±0.06% as in the wild-type strain) and incremented considerably when NfsA and NfsB were overexpressed (40.33%±9.42% and 59.68%±2.0% respectively).
PB Springer
YR 2012
FD 2012-01
LK http://hdl.handle.net/10498/20376
UL http://hdl.handle.net/10498/20376
LA eng
DS Repositorio Institucional de la Universidad de Cádiz
RD 12-nov-2026