Abstract

The enzymes involved in the microbial metabolism of many important phosphorus- or sulfur-containing xenobiotics, including organophosphate insecticides and precursors to organosulfate and organosulfonate detergents and dyestuffs have been characterized. In several instances their genes have been cloned and analysed. For phosphonate xenobiotics, the enzyme system responsible for the cleavage of the carbon-phosphorus bond has not yet been observed in vitro, though much is understood on a genetic level about phosphonate degradation. Phosphonate metabolism is regulated as part of the Pho regulon, under phosphate starvation control. For organophosphorothionate pesticides the situation is not so clear, and the mode of regulation appears to depend on whether the compounds are utilized to provide phosphorus, carbon or sulfur for cell growth. The same is true for organosulfonate metabolism, where different (and differently regulated) enzymatic pathways are involved in the utilization of sulfonates as carbon and as sulfur sources, respectively. Observations at the protein level in a number of bacteria suggest that a regulatory system is present which responds to sulfate limitation and controls the synthesis of proteins involved in providing sulfur to the cell and which may reveal analogies between the regulation of phosphorus and sulfur metabolism.

References

1

Hutzinger
O.
Veerkamp
W.
(
1981
)
Xenobiotic compounds with pollution potential
In:
Microbial Degradation of Xenobiotics and Recalcitrant Compounds
Leisinger
T.
Hütter
R.
Cook
A.M.
Nüesch
J.
, Eds) pp
3
45
Academic Press
,
London
.

2

Leisinger
T.
(
1983
)
Microorganisms and xenobiotic compounds
Experientia
,
39
,
1183
1191
.

3

Dalton
H.
Stirling
D.I.
(
1982
)
Cometabolism. Phil. Trans. Roy. Soc. Land. B
,
297
,
481
496
.

4

Janke
D.
Fritsche
W.
(
1985
)
Nature and significance of microbial cometabolism of xenobiotics
J. Basic Microbiol.
,
25
,
603
619
.

5

Neidhardt
F.C.
(
1987
)
Multigene systems and regulons
In:
Fscherichia coli and Salmonella typhimurium. Cellular and Molecular Biology
Neidhardt
F.C.
Ingraham
J.L.
Magasanik
B.
Low
K.B.
Schaechter
M.
Umbarger
H.E.
, Eds) pp
1313
1317
American Society for Microbiology
,
Washington, D.C
.

6

Magasanik
B.
Neidhardt
F.C.
(
1987
)
Regulation of carbon and nitrogen utilization
, 5th edn.In:
Escherichia coli and Salmonella typhimurium
Neidhardt
F.C.
Ingraham
J.L.
Magasanik
B.
Low
K.B.
Schaechter
M.
Umbarger
H.E.
, Eds) In Cellular and Molecular Biology, pp
1318
1325
American Society for Microbiology
,
Washington, D.C
.

7

MacGregor
C.H.
Wolff
J.A.
Arora
S.K.
Hylemon
P.B.
Phibbs
P.V.
Jr.
(
1992
)
Catabolite repression control in Pseudomonas aeruginosa
, In:
Pseudomonas
Galli
E.
Silver
S.
Witholt
B.
, Eds) In Molecular Biology and Biotechnology, pp
198
206
American Society of Microbiology
,
Washington, D.C
.

8

Cashel
M.
Rudd
K.E.
(
1987
)
The stringent response
, 5th edn.In:
Escherichia coli and Salmonella typhimurium
Neidhardt
F.C.
Ingraham
J.L.
Magasanik
B.
Low
K.B.
Schaechter
M.
Umbarger
H.E.
, Eds) In Cellular and Molecular Biology, pp
1410
1483
American Society for Microbiology
,
Washington, D.C
.

9

Lopez
J.M.
Dromerick
A.
Freese
E.
(
1981
)
Response of GTP concentration to nutritional changes and its significance for B. subtilis sporulation
J. Bacteriol.
,
146
,
605
613
.

10

Wanner
B.L.
(
1993
)
Gene regulation by phosphate in enteric bacteria
J. Cell. Biochem.
,
51
,
47
54
.

11

Kertesz
M.A.
Leisinger
T.
Cook
A.M.
(
1993
)
Proteins induced by sulfate limitation in Escherichia coli, Pseudomonas putida, or Staphylococcus aureus
J. Bacteriol.
,
175
,
1187
1190
.

12

Stock
J.B.
Ninfa
A.J.
Stock
A.M.
(
1989
)
Protein phosphorylation and regulation of adaptive reponses in bacteria
Microbiol. Rev.
,
53
,
450
490
.

13

Wanner
B.L.
(
1992
)
Is cross-regulation by phosphorylation of two-component response regulator proteins important in bacteria
J. Bacterial.
,
174
,
2053
2058
.

14

Hecker
M.
Völker
U.
(
1990
)
General stress proteins in Bacillus subtilis
FEMS Microbial. Ecol.
,
74
,
197
214
.

15

Deretic
V.
Konyecsni
W.M.
Mohr
C.D.
Martin
D.W.
Hibler
N.S.
(
1989
)
Common denominators of promoter control in Pseudomonas and other bacteria
Bio/Technology
,
7
,
1249
1254
.

16

Ghisalba
O.
Küenzi
M.
Tombo
G.M.R.
Schär
H.-P.
(
1987
)
Microbial degradation and utilization of selected organophosphorus compounds - strategies and applications
Chimia
,
41
,
206
215
.

17

Drake
G.L.
Calmari
T.A.
(
1983
)
Industrial uses of phosphonates
In:
The Role of Phosphonates in Living Systems
Hilderbrand
R.L.
, Ed) pp
171
194
CRC Press
,
Boca Raton, FL
.

18

Horiguchi
M.
(
1984
)
Chemistry of phosphonic and phosphinic acids
In:
Biochemistry of Natural C-P Compounds
Hori
T.
Horiguchi
M.
Hayashi
A.
, Eds) pp
8
22
Maruzen
,
Kyoto
.

19

Grossbard
E.
Atkinson
D.
(
1985
)
The herbicide glyphosate
Butterworths
,
London
.

20

Steinrücken
H.C.
Amrhein
N.
(
1980
)
The herbicide glyphosate is a potent inhibitor of 5-enolpyruvylshikimic acid-3-phosphate synthase
Biochem. Biophys. Res. Commun.
,
94
,
1207
1212
.

21

Balthazor
T.M.
Hallas
L.E.
(
1986
)
Glyphosate-degrading microorganisms from industrial activated sludge
Appl. Environ. Microbial.
,
51
,
432
434
.

22

Quinn
J.P.
Peden
J.M.M.
Dick
R.E.
(
1989
)
Carbon-phosphorus bond cleavage by Gram-positive and Gram-negative soil bacteria
Appl. Microbial. Biotechnol.
,
31
,
283
287
.

23

Moore
I.K.
Braymer
H.D.
Larson
A.D.
(
1983
)
Isolation of a Pseudomonas sp. which utilizes the phosphonate herbicide glyphosate
Appl. Environ. Microbial.
,
46
,
316
320
.

24

Talbot
H.W.
Johnson
L.M.
Munnecke
D.M.
(
1984
)
Glyphosate utilization by Pseudomonas sp. and Alcaligenes sp. isolated from environmental sources
Curr. Microbial.
,
10
,
255
259
.

25

Jacob
G.S.
Kimack
N.M.
Kishore
G.M.
Hallas
L.E.
Garbow
J.R.
Schaefer
J.
(
1988
)
Metabolism of glyphosate in Pseudomonas sp. strain
Lbr. Appl. Environ. Microbial.
,
54
,
2953
2958
.

26

Pipke
R.
Amrhein
N.
Jacob
G.S.
Kishore
G.M.
Schaefer
J.
(
1987
)
Metabolism of glyphosate in an Arthrobacter sp. GLP-1.
Eur. J. Biochem.
,
165
,
267
273
.

27

Liu
C.M.
Mclean
P.A.
Sookdeo
C.C.
Cannon
F.C.
(
1991
)
Degradation of the herbicide glyphosate by members of the family Rhizohiaceae
Appl. Environ. Microbial.
,
57
,
1799
1804
.

28

Wackett
L.P.
Shames
S.L.
Venditti
C.P.
Walsh
C.T.
(
1987
)
Bacterial carbon-phosphorus lyase: products, rates and regulation of phosphonic and phosphinic acid metabolism
J. Bacteriol.
,
169
,
710
717
.

29

Jacob
G.S.
Schaefer
J.
Stejskal
E.O.
McKay
R.A.
(
1985
)
Solid-state NMR determination of glyphosate metabolism in a Pseudomonas sp.
J. Biol. Chem.
,
260
,
5899
5904
.

30

Pipke
R.
Amrhein
N.
(
1988
)
Degradation of the phosphonate herbicide glyphosate by Arthrobacter atrocyaneus ATCC 13752
Appl. Environ. Microbiol.
,
54
,
1293
1296
.

31

Kertesz
M.
Elgorriaga
A.
Amrhein
N.
(
1991
)
Evidence for two distinct phosphonate-degrading enzymes (C-P lyases) in Arthrobacter sp. GLP-1
Biodegradation
,
2
,
53
66
.

32

Daughton
C.G.
Cook
A.M.
Alexander
M.
(
1979
)
Bacterial conversion of alkylphosphonates to natural products via carbon-phosphorus bond cleavage
J. Agric. Food Chem.
,
27
,
1375
1382
.

33

Schowanek
D.
Verstraete
W.
(
1990
)
Phosphonate utilization by bacterial cultures and enrichments from environmental samples
Appl. Environ. Microbiol.
,
56
,
895
903
.

34

Pipke
R.
Amrhein
N.
(
1988
)
Isolation and characterization of a mutant of Arthrobacter sp. strain GLP-1 which utilizes the herbicide glyphosate as its sole source of phosphorus and nitrogen
Appl. Environ. Microbiol.
,
54
,
2868
2870
.

35

Hallas
L.E.
Adams
W.J.
Heitkamp
M.A.
(
1992
)
Glyphosate degradation by immobilized bacteria - field studies with industrial waste-water effluent
Appl. Environ. Microbiol.
,
58
,
1215
1219
.

36

Shames
S.L.
Kuczkowski
R.L.
Labarge
M.S.
Wackett
L.P.
Walsh
C.T.
(
1987
)
Fragmentative and stereochemical isomerization probes for homolytic carbon to phosphorus bond scission catalyzed by bacterial carbon phosphorus lyase
Bioorg. Chem.
,
15
,
366
373
.

37

Cordeiro
M.L.
Pompliano
D.L.
Frost
J.W.
(
1986
)
Degradation and detoxification of organophosphonates: cleavage of the carbon to phosphorus bond
J. Am. Chem. Soc.
,
108
,
332
334
.

38

Frost
J.W.
Loo
S.
Cordeiro
M.L.
Li
D.
(
1987
)
Radical-based dephosphorylation and organophosphonate degradation
J. Am. Chem. Soc.
,
109
,
2166
2171
.

39

Ahn
Y.H.
Ye
Q.Z.
Cho
H.J.
Walsh
C.T.
Floss
H.G.
(
1992
)
Stereochemistry of carbon-phosphorus cleavage in ethylphosphonate catalyzed by C-P lyase from Escherichia coli
J. Am. Chem. Soc.
,
114
,
7953
7954
.

40

Wanner
B.L.
McSharry
R.
(
1982
)
Phosphate-controlled gene expression in E. coli K12 using MudI-directed lac fusions
J. Mol. Biol.
,
158
,
347
363
.

41

Wackett
L.P.
Venditti
C.P.
Walsh
C.T.
Wanner
B.L.
(
1987
)
Involvement of the phosphate regulon and the psiD locus in carbon-phosphorus lyase activity of Escherichia coli K-12
J. Bacteriol.
,
169
,
1753
1756
.

42

Wanner
B.L.
Boline
J.A.
(
1990
)
Mapping and molecular cloning of the phn (psiD) locus for phosphonate utilization in Escherichia coli
J. Bacteriol.
,
172
,
1186
1196
.

43

Chen
C.M.
Ye
Q.Z.
Zhu
Z.M.
Wanner
B.L.
Walsh
C.T.
(
1990
)
Molecular biology of carbon phosphorus bond cleavage - cloning and sequencing of the phn (psiD) genes involved in alkylphosphonate uptake and C-P lyase activity in Escherichia coli
B. J. Biol. Chem.
,
265
,
4461
4471
.

44

Metcalf
W.W.
Wanner
B.L.
(
1991
)
Involvement of the Escherichia coli phn (psiD) gene cluster in assimilation of phosphorus in the form of phosphonates, phosphate, Pi esters, and Pi
J. Bacteriol.
,
173
,
587
600
.

45

Wanner
B.L.
Metcalf
W.W.
(
1992
)
Molecular genetic studies of a 10.9-kb operon in Escherichia coli for phosphonate uptake and biodegradation
FEMS Microbiol. Lett.
,
100
,
133
139
.

46

Makino
K.
Kim
S.
Shinagawa
H.
Amemura
M.
Nakata
A.
(
1991
)
Molecular analysis of the cryptic and functional phn operons for phosphonate use in Escherichia coli K-12
J. Bacteriol.
,
173
,
2665
2672
.

47

Munnecke
D.M.
Johnson
L.M.
Talbot
H.W.
Barik
S.
(
1982
)
Microbial metabolism and enzymology of selected pesticides
In:
Biodegradation and Detoxification of Environmental Pollutants
Chakrabarty
A.M.
, Ed) pp
1
32
CRC Press
,
Boca Raton, FL
.

48

Johnson
L.M.
Talbot
H.W.
(
1983
)
Detoxification of pesticides by microbial enzymes
Experientia
,
39
,
702
706
.

49

Yoshida
T.
Sethunathan
N.
(
1973
)
A Flavobacterium that degrades diazinon and parathion
Can. J. Microbiol.
,
19
,
873
875
.

50

Barik
S.
Fletcher
J.S.
Munnecke
D.M.
(
1982
)
Enzymatic hydrolysis of malathion and other dithioate pesticides
Biotechnol. Lett.
,
4
,
795
798
.

51

Daughton
C.G.
Hsieh
D.P.
(
1977
)
Parathion utilization by bacterial symbionts in a chemostat
Appl. Environ. Microbiol.
,
34
,
175
184
.

52

Siddaramappa
R.
Rajaram
K.P.
Sethunathan
N.
(
1973
)
Degradation of parathion by bacteria isolated from flooded soil
Appl. Microbiol.
,
26
,
846
849
.

53

Serdar
C.M.
Gibson
D.T.
Lancaster
J.H.
Munnecke
D.M.
(
1982
)
Plasmid involvement in parathion hydrolysis by Pseudomonas diminuta
Appl. Environ. Microbiol.
,
44
,
246
249
.

54

Serdar
C.M.
Gibson
D.T.
(
1985
)
Enzymatic hydrolysis of organophosphates - cloning and expression of a parathion hydrolase gene from Pseudomonas diminuta
Bio/Technology
,
3
,
567
571
.

55

Bourquin
A.W.
(
1977
)
Degradation of malathion by salt marsh microorganisms
Appl. Environ. Microbiol.
,
33
,
356
362
.

56

Mulbry
W.W.
Karns
J.S.
(
1989
)
Purification and characterization of three parathion hydrolases from Gram-negative bacterial strains
Appl. Environ. Microbiol.
,
55
,
289
293
.

57

Munnecke
D.M.
(
1976
)
Enzymic hydrolysis of organophosphate insecticides, a possible pesticide disposal method
Appl. Environ. Microbiol.
,
32
,
7
13
.

58

Munnecke
D.M.
Hsieh
D.P.H.
(
1976
)
Pathways of microbial metabolism of parathion
Appl. Environ. Microbiol.
,
31
,
63
69
.

59

Rosenberg
A.
Alexander
M.
(
1979
)
Microbial cleavage of various organophosphorus insecticides
Appl. Environ. Microbiol.
,
37
,
886
891
.

60

de Matteis
F.
(
1989
)
Phosphorothionates
, 5th edn. (
Damani
L.A.
, Ed) In:
Sulphur-Containing Drugs and Related Organic Compounds
, In Metabolism of Sulphur Functional Groups, pp
9
34
Ellis Horwood
,
Chichester
.

61

McDaniel
C.S.
Harper
L.L.
Wild
J.R.
(
1988
)
Cloning and sequencing of a plasmid-borne gene (opd) encoding a phosphotriesterase
J. Bacteriol.
,
170
,
2306
2311
.

62

Mulbry
W.W.
Karns
J.S.
(
1989
)
Parathion hydrolase specified by the Flauobacterium opd gene - relationship between the gene and protein
J. Bacteriol.
,
171
,
6740
6746
.

63

Donarski
W.J.
Dumas
D.P.
Heitmeyer
D.P.
Lewis
V.E.
Raushel
F.M.
(
1989
)
Structure-activity relationships in the hydrolysis of substrates by the phosphotriesterase from Pseudomonas diminuta
Biochemistry
,
28
,
4650
4655
.

64

Harper
L.L.
McDaniel
C.S.
Miller
C.E.
Wild
J.R.
(
1988
)
Dissimilar plasmids isolated from Pseudomonas diminuta MG and a Flauobacterium sp. (ATCC 27551) contain identical opd genes
Appl. Environ. Microbiol.
,
54
,
2586
2589
.

65

Serdar
C.M.
Rohde
M.F.
Murdock
D.C.
(
1989
)
Parathion hydrolase gene from Pseudomonas diminuta MG - subcloning, complete nucleotide sequence, and expression of the mature portion of the enzyme in Escherichia coli
Bio/Technology
,
7
,
1151
1155
.

66

Wolfenden
R.
Spence
G.
(
1967
)
Derepression of phosphomonoesterase and phosphodiesterase activities in Aerobacter aerogenes
Biochim. Biophys. Acta
,
146
,
296
298
.

67

Wanner
B.L.
(
1987
)
Bacterial alkaline phosphatase gene regulation and the phosphate response in Escherichia coli
In:
Phosphate Metabolism and Cellular Regulation in Microorganisms
Torriani-Gorini
F.G.
Rothman
S.
Silver
S.
Wright
A.
Yagil
E.
, Eds) pp
12
19
American Society for Microbiology
,
Washington, D.C
.

68

Wanner
B.L.
(
1987
)
Phosphate regulation of gene expression in Escherichia coli
, 5th edn.In:
Eseherichia coli and Salmonella typhimurium
Neidhardt
F.C.
Ingraham
J.L.
Magasanik
B.
Low
K.B.
Schaechter
M.
Umbarger
H.E.
, Eds) In Cellular and Molecular Biology, pp
1326
1333
American Society for Microbiology
,
Washington, D.C
.

69

Cook
A.M.
Daughton
C.G.
Alexander
M.
(
1978
)
Phosphorus-containing pesticide breakdown products: quantitative utilization as phosphorus sources for bacteria
Appl. Environ. Microbiol.
,
36
,
668
672
.

70

Cook
A.M.
Alexander
M.
Daughton
C.G.
(
1980
)
Desulfuration of dialkyl thiophosphoric acids by a pseudomonad
Appl. Environ. Microbiol.
,
39
,
463
465
.

71

Wanner
B.L.
(
1990
)
Phosphorus assimilation and its control of gene expression in Escherichia coli
In:
The Molecular Basis of Bacterial Metabolism
Hauska
G.
Thauer
R.
, Eds) pp
152
163
Springer
,
Heidelberg
.

72

Vanbogelen
R.A.
Sankar
P.
Clark
R.L.
Bogan
J.A.
Neidhardt
F.C.
(
1992
)
The gene-protein database of Escherichia coli
5th edn.,
13
, In:
Electrophoresis
, pp
1014
1054
Weinheim
,
FRG
.

73

Pipke
R.
Schulz
A.
Amrhein
N.
(
1987
)
Uptake of glyphosate by an Arthrobacter sp.
Appl. Environ. Microbiol.
,
53
,
974
978
.

74

Fitzgibbon
J.
Braymer
H.D.
(
1988
)
Phosphate starvation induces uptake of glyphosate by Pseudomonas sp. strain PG2982
Appl. Environ. Microbiol.
,
54
,
1886
1888
.

75

Leidner
H.
Gloor
R.
Wüest
D.
Wuhrmann
K.
(
1980
)
The influence of the sulphonic group on the biodegradability of n-alkylbenzene sulphonates
Xenobiotica
,
10
,
47
56
.

Damani, 1989

Damani
L.A.
(
1989
)
Sulphur-Containing Drugs and Related Organic Compounds
, In:
Chemistry, Biochemistry and Toxicology
Elks Horwood
,
Chichester
.

77

Thayer
A.M.
(
1993
)
Soaps and detergents
Chem. Eng. News
,
71
,
26
47
.

78

Swisher
R.D.
(
1987
)
Surfactant biodegradation
, In:
Marcel Dekker
Springer
,
New York, NY
.

79

Painter
H.A.
(
1992
)
Anionic surfactants
In:
The Handbook of Environmental Chemistry
Hutzinger
O.
, Ed) pp
1
88
Springer
,
Berlin
.

80

Sörbo
B.
(
1987
)
Sulfate: turbidimetric and nephelometric methods
Methods Enzymol
,
143
,
3
6
.

81

Small
H.
(
1989
)
Ion chromatography
Plenum
,
New York, NY
.

82

Williams
R.J.
(
1982
)
The separation of ionic organosulfur compounds by ion chromatography
J. Chromatogr.
,
20
,
560
565
.

83

Cain
R.B.
(
1981
)
Microbial degradation of surfactants and ‘builder’ components
In:
Microbial Degradation of Xenobiotics and Recalcitrant Compounds
Leisinger
T.
Hütter
R.
Cook
A.M.
Nüesch
J.
, Eds) pp
325
370
Academic Press
,
London
.

84

Schöberl
P.
(
1989
)
Basic principles of LAS biodegradation
Tenside Surfactants Deterg.
,
26
,
86
94
.

85

Locher
H.H.
Leisinger
T.
Cook
A.M.
(
1991
)
Sulphobenzoate 3,4-dioxygenase - purification and properties of a desulphonative 2-component enzyme system from Comamonas testosteroni T-2
Bioehem. J.
,
274
,
833
842
.

86

Thurnheer
T.
Zürrer
D.
Höglinger
O.
Leisinger
T.
Cook
A.M.
(
1990
)
Initial steps in the degradation of benzenesulfonic acid, 4-toluenesulfonic acid and orthanilic acid in Alcaligenes sp. strain O-1
Biodegradation
,
1
,
55
64
.

87

Thurnheer
T.
Cook
A.M.
Kohler
T.
Leisinger
T.
(
1986
)
Orthanilic acid and analogs as carbon sources for bacteria - growth physiology and enzymic desulfonation
J. Gen. Microbiol.
,
132
,
1215
1220
.

88

Brilon
C.
Beckmann
W.
Knackmuss
H.J.
(
1981
)
Catabolism of naphthalenesulfonic acids by Pseudomonas sp. A3 and Pseudomonas sp. C22
Appl. Environ. Microbiol.
,
42
,
44
55
.

89

Nortemann
B.
Knackmuss
H.J.
Rast
H.G.
(
1986
)
Bacterial communities degrading aminonaphthalene-2sulfonates and hydroxynaphthalene-2-sulfonates
Appl. Environ. Microbiol.
,
52
,
1195
1202
.

90

Wittich
R.M.
Knackmuss
H.J.
Rast
H.G.
(
1988
)
Degradation of naphthalene-2,6-disulfonic and naphthalene-1,6-disulfonic acid by a Morarella sp.
Appl. Environ. Microbiol.
,
54
,
1842
1847
.

91

Zürrer
D.
Cook
A.M.
Leisinger
T.
(
1987
)
Microbial desulfonation of substituted naphthalenesuffonic acids and benzenesulfonic acids
Appl. Environ. Microbiol
,
53
,
1459
1463
.

92

Zürrer
D.
(
1989
)
Mikrobielle Desulfonierung aromatischer Sulfonsäuren
, In:
Doctoral Dissertation No. 9049
Eidgen. Tech. Hochschule
,
Zurich
.

93

Kertesz
M.A.
Kölbener
P.
Stockinger
H.
Beil
S.
Cook
A.M.
(
1994
)
Desuffonation of linear alkylbenzenesulfonate surfactant and related compounds by bacteria
Appl. Environ. Microbial.
,
60
,
2296
2303
.

94

Junker
F.
Field
J.A.
Bangerter
F.
Ramsteiner
K.
Kohler
H.-P.
Joannou
C.L.
Mason
J.R.
Leisinger
T.
Cook
A.M.
(
1994
)
Oxygenation and spontaneous deamination of 2-aminobenzenesulphonic acid in Alcaligenes sp. strain 0–1 with subsequent meta ring cleavage and spontaneous desulphonation to 2-hydroxymuconic acid
Biochem. J.
,
300
,
429
436
.

95

Feigel
B.J.
Knackmuss
H.J.
(
1988
)
Bacterial catabolism of sulfanilic acid via catechol-4-sulfonic acid
FEMS Microbiol. Lett.
,
55
,
113
117
.

96

Feigel
B.J.
Knackmuss
H.-J.
(
1993
)
Syntrophic interactions during degradation of 4-aminobenzenesulfonic acid by a two species bacterial culture
Arch. Microbiol.
,
159
,
124
130
.

97

Thysse
G.J.E.
Wanders
T.H.
(
1974
)
Initial steps in the degradation of n-alkane-l-sulphonates by Pseudomonas
Antonie van Leeuwenhoek
,
40
,
25
37
.

98

Jahnke
M.
El-Banna
T.
Klintworth
R.
Auling
G.
(
1990
)
Mineralization of orthanilic acid is a plasmid-associated trait in Alcaligenes sp. O-1
J. Gen. Microbiol.
,
136
,
2241
2249
.

99

Hooper
S.W.
Locher
H.H.
Cook
A.M.
Leisinger
T.
(
1990
)
Genetic and functional analysis of the 4-toluenesulfonate pathway of Comamonas (Pseudomonas) testosteroni T-2
, In:
Abstr. Annu. Meet. Am. Soc. Microbial.
Anaheim
,
Cal
.

100

Dimkov
R.
Konstantinova
R.
Todorov
Z.
(
1985
)
Effect of inorganic ingredients of detergents on the biodegradation of alkylbenzene sulphonates
Zentralbl. Mikrobiol.
,
140
,
91
95
.

101

Dodgson
K.S.
White
G.F.
Fitzgerald
J.W.
(
1982
)
Sulfatases of microbial origin
CRC Press
,
Boca Raton, FL
.

102

Payne
W.J.
Faisal
V.E.
(
1963
)
Bacterial utilization of dodecylsulfate and dodecyl benzenesulfonate
Appl. Microbiol.
,
11
,
339
344
.

103

Fitzgerald
J.W.
Dodgson
K.S.
Matcham
G.W.J.
(
1977
)
Secondary alkylsulfatases in a strain of Comanmnas terrigena
Biochem. J.
,
149
,
477
480
.

104

Fitzgerald
J.W.
Kight
L.C.
(
1977
)
Physiological control of alkylsulfatase synthesis in Pseuclomonas aeruginosa: effects of glucose, glucose analogues and sulfur
Can. J. Microbial.
,
23
,
1456
1464
.

105

Fitzgerald
J.W.
Dodgson
K.S.
Payne
W.J.
(
1974
)
Induction of primary alkylsulphatases and metabolism of sodium hexan-1-yl sulphate by Pseudomonas C 12B
Biochem. J.
,
138
,
63
69
.

106

Cloves
J.M.
Dodgson
K.S.
Fitzgerald
J.W.
White
G.F.
(
1980
)
Specificity of P2 primary alkylsulfohydrolase induction in the detergent-degrading bacterium Pseudornonas C12B - effects of alkanesulphonates, alkyl sulfates and other related compounds
Biochem. J.
,
185
,
13
21
.

107

Dodgson
K.S.
Fitzgerald
J.W.
Payne
W.J.
(
1974
)
Chemically defined inducers of alkylsulphatases present in Pseudomonas C12B
Biochem. J.
,
138
,
53
62
.

108

Fitzgerald
J.W.
Kight-Olliff
L.C.
Stewart
G.J.
Beauchamp
N.F.
(
1978
)
Reversal of succinate-mediated catabolite repression of alkylsulfatase in Pseudomonas aeruginosa by 2,4-dinitrophenol and by sodium malonate
Can. J. Microbial.
,
24
,
1567
1573
.

109

Speir
T.W.
Ross
D.J.
(
1978
)
Soil phosphatase and sulphatase
In:
Soil Enzymes
Burns
R.G.
, Ed) pp
198
235
Academic Press
,
New York, NY
.

110

Fitzgerald
J.W.
(
1976
)
Sulfate ester formation and hydrolysis: a potentially important yet often ignored aspect of the sulfur cycle of aerobic soils
Bacterial. Rev.
,
40
,
628
721
.

Fitzgerald, 1978

Fitzgerald
J.W.
(
1978
)
Naturally occurring organosulfur compounds in soil
In:
Sulfur in the Environment
Nriagu
J.O.
, Ed) pp
391
443
Wiley
,
New York, NY
.

112

Murooka
Y.
Ishibashi
K.
Yasumoto
M.
Sasaki
M.
Sugino
H.
Azakami
H.
Yamashita
M.
(
1990
)
A sulfur-regulated and tyramine-regulated Klebsiella aerogenes operon containing the arylsulfatase (atsA) gene and the atsB gene
J. Bacterial.
,
772
,
2131
2140
.

113

Adachi
T.
Murooka
Y.
Harada
T.
(
1975
)
Regulation of arylsulfatase synthesis by sulfur compounds in Klebsiella aerogenes
J. Bacterial.
,
121
,
29
35
.

114

Adachi
T.
Okamura
H.
Murooka
Y.
Harada
T.
(
1974
)
Catabolite repression and derepression of arylsulfatase synthesis in Klebsiella aerogenes
J. Bacterial.
,
120
,
880
885
.

115

Murooka
Y.
Harada
T.
Yim
M.H.
(
1980
)
Formation and purification of Serratia marcescens arylsulfatase
Appl. Environ. Microbial.
,
39
,
812
817
.

116

Henderson
M.J.
Milazzo
F.H.
(
1979
)
Arylsulfatase in Salmonella typhimurium: detection and influence of carbon source and tyramine on its synthesis
J. Bacteriol.
,
139
,
80
87
.

117

Rammler
D.H.
Grado
C.
Fowler
L.R.
(
1964
)
Sulfur metabolism of Aerobacter aerogenes 1. A repressible sulfatase
Biochemistry
,
3
,
224
230
.

118

Yamada
T.
Murooka
Y.
Harada
T.
(
1978
)
Comparative immunological studies on arylsulfatase in bacteria of the family Enterobacteriaceae: occurrence of latent arylsulfatase protein regulated by sulfur compounds and tyramine
J. Bacteriol.
,
133
,
536
541
.

119

Milazzo
F.H.
Fitzgerald
J.W.
(
1967
)
The effect of some cultural conditions on the arylsulfatase of Proteus rettgeri
Can. J. Microbiol.
,
13
,
659
664
.

120

Murooka
Y.
Harada
T.
(
1981
)
Regulation of derepressed synthesis of arylsulfatase by tyramine oxidase in Salmonella typhimurium
J. Baeteriol.
,
145
,
796
802
.

121

Okamura
H.
Murooka
Y.
Harada
T.
(
1977
)
Tyramine oxidase and regulation of arylsulfatase synthesis in Klebsiella aerogenes
J. Bacteriol.
,
129
,
59
65
.

122

Oka
M.
Harada
T.
Murooka
Y.
(
1980
)
Unstable mutations for constitutive synthesis of tyramine oxidase and arylsulfatase in Klebsiella aerogenes
Agric. Biol. Chem.
,
44
,
2429
2435
.

123

Okamura
H.
Murooka
Y.
Harada
T.
(
1976
)
Regulation of tyramine oxidase synthesis in Klebsiella aerogenes
J. Bacteriol.
,
127
,
24
31
.

124

Sugino
H.
Sasaki
M.
Azakami
H.
Yamashita
M.
Murooka
Y.
(
1992
)
A monoamine-regulated Klebsiella aerogenes operon containing the monoamine oxidase structural gene (maoA) and the maoC gene
J. Bacteriol.
,
174
,
2485
2492
.

125

Yamashita
M.
Murooka
Y.
(
1984
)
Use of lac gene fusions to study regulation of tyramine oxidase, which is involved in derepression of latent arylsulfatase in Escherichia coli
Agric. Biol. Chem.
,
48
,
1459
1470
.

126

Azakami
H.
Sugino
H.
Murooka
Y.
(
1992
)
Cloning and nucleotide sequence of a negative regulator gene for Klebsiella aerogenes arylsulfatase synthesis and identification of the gene as folA.J.
Bacteriol.
,
174
,
2344
2351
.

127

Harada
T.
(
1964
)
The formation of sulphatases in Pseudomonas aeruginosa
Biochim. Biophys. Acta
,
81
,
193
196
.

128

Harada
T.
Spencer
B.
(
1964
)
Repression and induction of arylsulphatase synthesis in Aerobacter aerogenes
Biochem. J.
,
93
,
373
378
.

129

Paietta
J.V.
(
1992
)
Production of the CYS3 regulator, a bZIP DNA-binding protein, is sufficient to induce sulfur gene expression in Neurospora crassa
Mol. Cell Biol.
,
12
,
1568
1577
.

130

Mazel
D.
Marliére
P.
(
1989
)
Adaptive eradication tit methionine and cysteine from bacterial light-harvesting proteins
Nature
,
341
,
245
248
.

131

Kredich
N.M.
(
1992
)
The molecular basis for positive regulation of cys promoters in Salmonella typhinmrium and Escherichia coli
Mol. Microbiol.
,
6
,
2747
2753
.

132

Kredich
N.M.
(
1987
)
Biosynthesis of cysteine
, Third EditionIn:
Escherichia coli and Salmonella typhimurium
Neidhardt
F.C.
Ingraham
J.L.
Magasanik
B.
Low
K.B.
Schaechter
M.
Umbarger
H.E.
, Eds) In Cellular and Molecular Biology, pp
419
428
American Society for Microbiology
,
Washington, D.C
.

133

Ostrowski
J.
Kredich
N.M.
(
1990
)
In vitro interactions of CysB protein with the cysJIH promoter of Salmonella typhimurium - inhibitory effects of sulfide
J. Bacteriol.
,
172
,
779
785
.

134

Kredich
N.M.
Becker
M.A.
Tomkins
G.M.
(
1969
)
Purification and characterization of cysteine synthetase, a bifunctional protein complex, from Salmonella typhimurium
J. Biol. Chem.
,
244
,
2428
2439
.

135

Schreiner
O.
Lien
T.
Knutsen
G.
(
1975
)
The capacity for arylsulfatase synthesis in synchronous and synchronized cultures of Chlamydomonas reinhardti
Biochim. Biophys. Acta
,
384
,
180
193
.

136

Jacobson
S.E.
Metzenberg
R.L.
(
1977
)
Control of arylsulphatase in a serine auxotroph of Neurospora
J. Bacteriol.
,
130
,
1397
1398
.

137

Fitzgerald
J.W.
Payne
W.J.
(
1972
)
The regulation of arylsulfatase activity in Pseudomonas C12B
Microbios
,
6
,
147
156
.

138

Cook
A.M.
(
1989
)
Combined carbon and phosphorus or carbon and sulfur substrates
In:
Mixed and Multiple Substrates and Feedstocks
Hamer
G.
Egli
T.
Snozzi
M.
, Eds) pp
71
83
Hartung-Gorre Verlag
,
Konstanz
.

139

Seitz
A.P.
Leadbetter
E.R.
Godchaux
W.
III
(
1993
)
Utilization of sulfonates as sole sulfur source by soil bacteria including Comamonas acidovorans
Arch. Microbiol.
,
159
,
440
444
.

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