Microbial transformation of aniline derivatives: regioselective biotransformation and detoxification of 2-phenylenediamine by Bacillus cereus strain PDa-1.
A bacterial isolate, strain PDa-1, grew well on basal medium supplemented with 2-phenylenediamine, sucrose, and ammonium nitrate and completely transformed 2-phenylenediamine. The isolate was identified as Bacillus cereus. The product formed from 2-phenylenediamine was identified by EI-MS and NMR as 2-aminoacetanilide; whole cells converted 2-phenylenediamine to the product with a 76% molar yield. Whole cells also showed a broad substrate specificity toward 20 of 26 tested arylamines with substituent groups of various size and positions. Especially 2-aminobenzoic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, and 2-aminofluorene were converted completely to the corresponding product with an aminoacetyl group. Cell extracts of strain PDa-1 had a high arylamine N-acetyltransferase activity. The partially purified enzyme converted 2-phenylenediamine to 2-aminoacetanilide. Strain PDa-1 constitutively expressed the enzyme in the absence of 2-phenylenediamine. Effects of 2-phenylenediamine and 2-aminoacetanilide on growth indicated that this enzyme probably plays a role in the detoxification of toxic arylamines in this strain.
Takenaka
Shinji
S
Department of Biofunctional Chemistry, Faculty of Agriculture, Kobe University, 1-1 Rokkodai, Kobe 657-8501, Japan.
Mulyono
Sasano
Yasuhiro
Y
Takahashi
Yuka
Y
Murakami
Shuichiro
S
Aoki
Kenji
K
D000814:Aniline Compounds / Q000378:metabolism*; D001191:Arylamine N-Acetyltransferase / Q000032:analysis / Q000378:metabolism*; D001409:Bacillus cereus / Q000145:classification / Q000235:genetics / Q000378:metabolism*; D001673:Biodegradation, Environmental; D001711:Biotransformation; D049109:Cell Proliferation; D010655:Phenylenediamines / Q000302:isolation & purification / Q000378:metabolism*; D013045:Species Specificity
D000814:Aniline Compounds; D010655:Phenylenediamines; D001191:Arylamine N-Acetyltransferase