Steroid degradation in Comamonas testosteroni

Journal of Steroid Biochemistry and Molecular Biology

Volumn 129, Issue 1-2, 2012, Pages 4-14

  Horinouchi, Masae ^a   Hayashi, Toshiaki ^a   Kudo, Toshiaki ^a,b  

^a RIKEN   (Japan)

^b NAGASAKI UNIVERSITY   (Japan)

Author keywords

Comamonas testosteroni; Steroid

Indexed keywords

3ALPHA HYDROXYSTEROID DEHYDROGENASE; BOLDIONE; CHOLIC ACID; RNA POLYMERASE; STEROID DELTA ISOMERASE; TESTOSTERONE; TRANSCRIPTION FACTOR LUXR;

AMINO ACID SEQUENCE; AROMATIZATION; ARTICLE; CHEMICAL BOND; COMAMONAS TESTOSTERONI; DEGRADATION; DNA FLANKING REGION; FATTY ACID OXIDATION; GENE CLUSTER; HYDROLYSIS; HYDROXYLATION; NONHUMAN; NUCLEOTIDE SEQUENCE; PROMOTER REGION; RHODOCOCCUS EQUI;

COMAMONAS TESTOSTERONI; GENES, BACTERIAL; HYDROXYSTEROID DEHYDROGENASES; KETOSTEROIDS; MULTIGENE FAMILY; STEROID ISOMERASES; STEROIDS;

BACTERIA (MICROORGANISMS); COMAMONAS TESTOSTERONI; NOCARDIA;

EID: 84857783567     PISSN: 09600760     EISSN: 18791220     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2010.10.008     Document Type: Article

References (87)

1. R.M. Dodson, and R.D. Muir Microbiological transformations. II. Microbiological aromatization of steroids J. Am. Chem. Soc. 80 1958 5004 5005
2. R.M. Dodson, and R.D. Muir Microbiological transformations. III. The hydroxylation of steroids at C-9 J. Am. Chem. Soc. 80 1958 6148
3. D.A. Shaw, L.F. Borkenhagen, and P. Talalay Enzymatic oxidation of steroids by cell-free extracts of Pseudomonas testosteroni: isolation of cleavage products of ring A Proc. Natl. Acad. Sci. U.S.A. 54 1965 837 844
4. R.M. Dodson, and R.D. Muir Microbiological transformations. IV. The microbiological aromatization of steroids J. Am. Chem. Soc. 83 1961 4627 4631
5. C.J. Sih Mechanisms of steroid oxidation by microorganisms Biochim. Biophys. Acta 62 1962 541 547
6. C.J. Sih, and K.C. Wang Mechanisms of steroid oxidation by microorganisms. II. Isolation and characterization of 3aα-H-4α-[3'- propionic acid]-7aβ-methylhezahydro-1,5-indanedione J. Am. Chem. Soc. 85 1963 2135 2137
7. K.C. Wang, and C.J. Sih Mechanisms of steroid oxidation by microorganisms. IV. Seco intermediates Biochemistry 2 1963 1238 1243
8. C.J. Sih, S.S. Lee, Y.K. Tsong, and K.C. Wang 3,4-Diydroxy-9,10- secoandrosta-1,3,5(10)-triene-9,17-dione. An intermediate in the microbiological degradation of ring A of androst-4-ene-3,17-dione J. Am. Chem. Soc. 87 1965 1385 1386
9. C.J. Sih, S.S. Lee, Y.K. Tsong, and K.C. Wang Mechanisms of steroid oxidation by microorganisms. VIII. 3,4-Dihydroxy-9,10-secoandrosta-1,3,5(10)- triene-9,17-dione, an intermediate in the microbiological degradation of ring A of androst-4-ene-3,17-dione J. Biol. Chem. 241 1966 540 550
10. A.W. Coulter, and P. Talalay Studies on the microbial degradation of steroid ring A J. Biol. Chem. 243 1968 3238 3247
11. S. Hayakawa, and S. Hashimoto (+)-(5R)-Methyl-4-oxo-octane-1,8-dioic Acid, microbiological degradation product from rings C and D of cholic acid Biochem. J. 112 1969 127 128
12. R.A. Leppik, R.J. Park, and M.G. Smith Aerobic catabolism of bile acids Appl. Environ. Microbiol. 44 1982 771 776 (Pubitemid 13213342)
13. M. Horinouchi, T. Yamamoto, K. Taguchi, H. Arai, and T. Kudo Meta-cleavage enzyme gene tesB is necessary for testosterone degradation in Comamonas testosteroni TA441 Microbiology 147 2001 3367 3375 (Pubitemid 33150343)
14. M. Horinouchi, T. Hayashi, T. Yamamoto, and T. Kudo A new bacterial steroid degradation gene cluster which consists of aromatic compound degradation genes for seco-steroids and 3-ketosteroid dehydrogenase genes in Comamonas testosteroni TA441 Appl. Environ. Microbiol. 69 2003 4421 4430 (Pubitemid 36992896)
15. M. Horinouchi, T. Hayashi, H. Koshino, T. Yamamoto, and T. Kudo Gene encoding the hydrolase for the product of the meta-cleavage reaction in testosterone degradation by Comamonas testosteroni Appl. Environ. Microbiol. 69 2003 2139 2152 (Pubitemid 36443631)
16. M. Horinouchi, T. Hayashi, and T. Kudo The genes encoding the hydroxylase of 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione in steroid degradation in Comamonas testosteroni TA441 J. Steroid Biochem. Mol. Biol. 92 2004 143 154 (Pubitemid 39535855)
17. M. Horinouchi, T. Kurita, T. Yamamoto, E. Hatori, T. Hayashi, and T. Kudo Steroid degradation gene cluster of Comamonas testosteroni consisting of 18 putative genes from meta-cleavage enzyme gene tesB to regulator gene tesR Biochem. Biophys. Res. Commun. 324 2004 597 604 (Pubitemid 39359193)
18. M. Horinouchi, T. Hayashi, T. Kurita, and T. Kudo Identification of 9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid, 4-hydroxy-2-oxohexanoic acid, and 2-hydroxyhexa-2,4-dienoic acid and related enzymes involved in testosterone degradation in Comamonas testosteroni TA441 Appl. Environ. Microbiol. 71 2005 5275 5281 (Pubitemid 41338258)
19. P. Talalay, and V.S. Wang Enzymic isomerization of delta5-3-ketosteroids Biochim. Biophys. Acta 18 1955 300 301
20. P. Talalay, and P.I. Marcus Enzymatic formation of 3 alpha- hydroxysteroids Nature 173 1954 1189 1190
21. P. Talalay, M.M. Dobson, and D.F. Tapley Oxidative degradation of testosterone by adaptive enzymes Nature 170 1952 620 621
22. S. Genti-Raimondi, M.E. Tolmasky, L.C. Patrito, A. Flury, and L.A. Actis Molecular cloning and expression of the β-hydroxysteroid dehydrogenase gene from Pseudomonas testosteroni Gene 105 1991 43 49
23. E. Mobus, and E. Maser Molecular cloning, overexpression, and characterization of steroid-inducible 3α-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testosteroni. A novel member of the short-chain dehydrogenase/reductase superfamily J. Biol. Chem. 273 1998 30888 30896 (Pubitemid 28533089)
24. A. Kuliopulos, D. Shortle, and P. Talalay Isolation and sequencing of the gene encoding Δ5-3-ketosteroid isomerase of Pseudomonas testosteroni: overexpression of the protein Proc. Natl. Acad. Sci. U.S.A. 84 1987 8893 8897
25. K.Y. Choi, and W.F. Benisek Cloning of the gene for Δ5-3- ketosteroid isomerase from Pseudomonas testosteroni Gene 58 1987 257 264 (Pubitemid 17167292)
26. P. Plesiat, M. Grandguillot, S. Harayama, S. Vragar, and Y. Michel-Briand Cloning, sequencing, and expression of the Pseudomonas testosteroni gene encoding 3-oxosteroid Δ1-dehydrogenase J. Bacteriol. 173 1991 7219 7227
27. C. Florin, T. Kohler, M. Grandguillot, and P. Plesiat Comamonas testosteroni 3-ketosteroid-Δ4(5α)-dehydrogenase: gene and protein characterization J. Bacteriol. 178 1996 3322 3330 (Pubitemid 26170023)
28. M. Horinouchi, T. Hayashi, H. Koshino, and T. Kudo ORF18-disrupted mutant of Comamonas testosteroni TA441 accumulates significant amounts of 9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid and its derivatives after incubation with steroids J. Steroid Biochem. Mol. Biol. 101 2006 78 84 (Pubitemid 44301879)
29. Y.F. Ma, Y. Zhang, J.Y. Zhang, D.W. Chen, Y. Zhu, H. Zheng, S.Y. Wang, C.Y. Jiang, G.P. Zhao, and S.J. Liu The complete genome of Comamonas testosteroni reveals its genetic adaptations to changing environments Appl. Environ. Microbiol. 75 2009 6812 6819
30. R.M. Schultz, E.V. Groman, and L.L. Engel 3(17)β-Hydroxysteroid dehydrogenase of Pseudomonas testosteroni. A convenient purification and demonstration of multiple molecular forms J. Biol. Chem. 252 1977 3775 3783 (Pubitemid 8116115)
31. P. Minard, M.D. Legoy, and D. Thomas 3β, 17β-Hydroxysteroid dehydrogenase of Pseudomonas testosteroni. Kinetic evidence for the bifunctional activity at a common catalytic site FEBS Lett. 188 1985 85 90 (Pubitemid 16248396)
32. S.J. Yin, N. Vagelopoulos, G. Lundquist, and H. Joernvall Pseudomonas 3β-hydroxysteroid dehydrogenase. Primary structure and relationships to other steroid dehydrogenases Eur. J. Biochem. 197 1991 359 365
33. J. Benach, C. Filling, U.C.T. Oppermann, P. Roversi, G. Bricogne, K.D. Berndt, H. Jornvall, and R. Ladenstein Structure of bacterial 3β/17β-hydroxysteroid dehydrogenase at 1.2 resolution: a model for multiple steroid recognition Biochemistry 41 2002 14659 14668 (Pubitemid 35476868)
34. J.E. Cabrera, G. Panzetta-Dutari, J.L. Pruneda, and S. Genti-Raimondi A new Comamonas testosteroni steroid-inducible gene: cloning and sequence analysis J. Steroid Biochem. Mol. Biol. 63 1997 91 98 (Pubitemid 28018141)
35. J.E. Cabrera, J.L. Pruneda Paz, and S. Genti-Raimondi Steroid-inducible transcription of the 3β/17β-hydroxysteroid dehydrogenase gene (3β/17β-hsd) in Comamonas testosteroni J. Steroid Biochem. Mol. Biol. 73 2000 147 152 (Pubitemid 30488095)
36. J.L. Pruneda-Paz, M. Linares, J.E. Cabrera, and S. Genti-Raimondi Identification of a novel steroid inducible gene associated with the beta hsd locus of Comamonas testosteroni J. Steroid Biochem. Mol. Biol. 88 2004 91 100 (Pubitemid 38326601)
37. M. Horinouchi, T. Kurita, T. Hayashia, and T. Kudo Steroid degradation genes in Comamonas testosteroni TA441: Isolation of genes encoding a Δ4(5)-isomerase and 3α- and 3β-dehydrogenases and evidence for a 100 kb steroid degradation gene hot spot J. Steroid Biochem. Mol. Biol. 122 2010 253 263
38. U.C.T. Oppermann, I. Belai, and E. Maser Antibiotic resistance and enhanced insecticide catabolism as consequences of steroid induction in the Gram-negative bacterium Comamonas testosteroni J. Steroid Biochem. Mol. Biol. 58 1996 217 223 (Pubitemid 26284519)
39. P.I. Marcus, and P. Talalay Induction and purification of alpha- and beta-hydroxysteroid dehydrogenases J. Biol. Chem. 218 1956 661 674
40. J.H. Abalain, S. Di Stefano, M.L. Abalain-Colloc, and H.H. Floch Cloning, sequencing and expression of Pseudomonas testosteroni gene encoding 3 alpha-hydroxysteroid dehydrogenase J. Steroid Biochem. Mol. Biol. 55 1995 233 238
41. U.C.T. Oppermann, and E. Maser Characterization of a 3α- hydroxysteroid dehydrogenase/carbonyl reductase from the gram-negative bacterium Comamonas testosteroni Eur. J. Biochem. 241 1996 744 749 (Pubitemid 26379375)
42. G. Xiong, and E. Maser Regulation of the steroid-inducible 3α-hydroxysteroid dehydrogenase/carbonyl reductase gene in Comamonas testosteroni J. Biol. Chem. 276 2001 9961 9970
43. G. Xiong, H.J. Martin, and E. Maser Identification and characterization of a novel translational repressor of the steroid-inducible 3α- hydroxysteroid dehydrogenase/carbonyl reductase gene in Comamonas testosteroni J. Biol. Chem. 278 2003 47400 47407 (Pubitemid 37523180)
44. F.H. Batzold, A.M. Benson, D.F. Covey, C.H. Robinson, and P. Talalay The delta 5-3-ketosteroid isomerase reaction: catalytic mechanism, specificity and inhibition Adv. Enzyme Regul. 14 1976 243 267
45. F.S. Kawahara, and P. Talalay Crystalline delta 5-3-ketosteroid isomerase J. Biol. Chem. 235 1960 1 2
46. F.S. Kawahara, S.F. Wang, and P. Talalay The preparation and properties of crystalline delta5-3-ketosteroid isomerase J. Biol. Chem. 237 1962 1500 1506
47. P. Talalay, and J. Boyer Preparation of crystalline Δ-5-3- ketosteroid isomerase from Pseudomonas testosteroni Biochim. Biophys. Acta 105 1965 389 392
48. H.S. Cho, N.C. Ha, G. Choi, H.J. Kim, D. Lee, K.S. Oh, K.S. Kim, W. Lee, K.Y. Choi, and B.H. Oh Crystal structure of Δ(5)-3-ketosteroid isomerase from Pseudomonas testosteroni in complex with equilenin settles the correct hydrogen bonding scheme for transition state stabilization J. Biol. Chem. 274 1999 32863 32868 (Pubitemid 129535321)
49. H.J. Lee, Y.J. Yoon, S. Jang do, C. Kim, H.J. Cha, B.H. Hong, K.Y. Choi, and H.C. Lee 15N NMR relaxation studies of Y14F mutant of ketosteroid isomerase: the influence of mutation on backbone mobility J. Biochem. 144 2008 159 166
50. A.F. Hofmann Bile acids, diarrhea, and antibiotics: data, speculation, and a unifying hypothesis J. Infect. Dis. 135 Suppl. 1977 S126 132
51. M. Podda, C. Ghezzi, P.M. Battezzati, E. Bertolini, A. Crosignani, M.L. Petroni, and M. Zuin Ursodeoxycholic acid for chronic liver diseases J. Clin. Gastroenterol. 2 10 Suppl. 1988 S25 31
52. M. Podda, M. Zuin, P.M. Battezzati, C. Ghezzi, C. de Fazio, and M.L. Dioguardi Efficacy and safety of a combination of chenodeoxycholic acid and ursodeoxycholic acid for gallstone dissolution: a comparison with ursodeoxycholic acid alone Gastroenterology 96 1989 222 229 (Pubitemid 19046286)
53. M. Podda, C. Ghezzi, P.M. Battezzati, A. Crosignani, M. Zuin, and A. Roda Effects of ursodeoxycholic acid and taurine on serum liver enzymes and bile acids in chronic hepatitis Gastroenterology 98 1990 1044 1050 (Pubitemid 20095860)
54. G. Mazzella, P. Parini, F. Bazzoli, N. Villanova, D. Festi, R. Aldini, A. Roda, A. Cipolla, C. Polimeni, and D. Tonelli Ursodeoxycholic acid administration on bile acid metabolism in patients with early stages of primary biliary cirrhosis Dig. Dis. Sci. 38 1993 896 902 (Pubitemid 23144633)
55. S. Guldutuna, M. Leuschner, N. Wunderlich, A. Nickel, S. Bhatti, K. Hubner, and U. Leuschner Cholic acid and ursodeoxycholic acid therapy in primary biliary cirrhosis. Changes in bile acid patterns and their correlation with liver function Eur. J. Clin. Pharmacol. 45 1993 221 225 (Pubitemid 23290371)
56. U. Leuschner Ursodeoxycholic acid therapy in primary biliary cirrhosis Scand. J. Gastroenterol. Suppl. 204 1994 40 46 (Pubitemid 24302611)
57. E. Roda, A. Cipolla, A. Salzetta, S. Marchetto, A. Pezzoli, E. Accogli, V. Novelli, C. Polimeni, C. Cerre, and G. Mazzella Influence of ursodeoxycholic acid on biliary lipids Scand. J. Gastroenterol. Suppl. 204 1994 16 18 (Pubitemid 24302606)
58. F.M. Konikoff, and T. Gilat Effects of fatty acid bile acid conjugates (FABACs) on biliary lithogenesis: potential consequences for non-surgical treatment of gallstones Curr. Drug Targets Immune. Endocr. Metabol. Disord. 5 2005 171 175 (Pubitemid 40766861)
59. M. Mikov, J.P. Fawcett, K. Kuhajda, and S. Kevresan Pharmacology of bile acids and their derivatives: absorption promoters and therapeutic agents Eur. J. Drug Metab. Pharmacokinet. 31 2006 237 251 (Pubitemid 44831781)
60. J. Koga, H. Kubota, S. Gomi, K. Umemura, M. Ohnishi, and T. Kono Cholic acid, a bile acid elicitor of hypersensitive cell death, pathogenesis-related protein synthesis, and phytoalexin accumulation in rice Plant Physiol. 140 2006 1475 1483 (Pubitemid 43956230)
61. T Shimizu, Y. Jikumaru, A. Okada, K. Okada, J. Koga, K. Umemura, E. Minami, N. Shibuya, M. Hasegawa, O. Kodama, H. Nojiri, and H. Yamane Effects of a bile acid elicitor, cholic acid, on the biosynthesis of diterpenoid phytoalexins in suspension-cultured rice cells Phytochemistry 69 2008 973 981 (Pubitemid 351222598)
62. M.E. Tenneson, J.D. Baty, R.F. Bilton, and A.N. Mason The degradation of cholic acid by Pseudomonas sp. N.C.I.B. 10590 Biochem. J. 184 1979 613 618 (Pubitemid 10183597)
63. R.J. Park The major neutral products of the aerobic catabolism of cattle bile by Pseudomonas sp. ATCC 31752 Steroids 38 1981 383 395 (Pubitemid 12176221)
64. A. Birkenmaier, J. Holert, H. Erdbrink, H.M. Moeller, A. Friemel, R. Schoenenberger, M.J. Suter, J. Klebensberger, and B. Philipp Biochemical and genetic investigation of initial reactions in aerobic degradation of the bile acid cholate in Pseudomonas sp. strain Chol1 J. Bacteriol. 189 2007 7165 7173 (Pubitemid 47557329)
65. M. Horinouchi, T. Hayashi, H. Koshino, M. Malon, T. Yamamoto, and T. Kudo Identification of genes involved in inversion of stereochemistry of a C-12 hydroxyl group in the catabolism of cholic acid by Comamonas testosteroni TA441 J. Bacteriol. 190 2008 5545 5554
66. S.S. Lee, and C.J. Sih Mechanisms of steroid oxidation by microorganisms. XII. Metabolism of hexahydroindanpropionic acid derivatives Biochemistry 6 1967 1395 1403
67. J.L. Pruneda-Paz, M. Linares, J.E. Cabrera, and S. Genti-Raimondi TeiR, a LuxR-type transcription factor required for testosterone degradation in Comamonas testosteroni J. Bacteriol. 186 2004 1430 1437 (Pubitemid 38248734)
68. A. Gohler, G. Xiong, S. Paulsen, G. Trentmann, and E. Maser Testosterone-inducible regulator is a kinase that drives steroid sensing and metabolism in Comamonas testosteroni J. Biol. Chem. 283 2008 17380 17390
69. M. Linares, J.L. Pruneda-Paz, L. Reyna, and S. Genti-Raimondi Regulation of testosterone degradation in Comamonas testosteroni J. Steroid Biochem. Mol. Biol. 112 2008 145 150
70. V. Rosch, K. Denger, D. Schleheck, T.H. Smits, and A.M. Cook Different bacterial strategies to degrade taurocholate Arch. Microbiol. 190 2008 11 18
71. D. Schleheck, T.P. Knepper, K. Fischer, and A.M. Cook Mineralization of individual congeners of linear alkylbenzenesulfonate by defined pairs of heterotrophic bacteria Appl. Environ. Microbiol. 70 2004 4053 4063 (Pubitemid 38969748)
72. M.A. Sanchez, and B. Gonzalez Genetic characterization of 2,4,6-trichlorophenol degradation in Cupriavidus necator JMP134 Appl. Environ. Microbiol. 73 2007 2769 2776 (Pubitemid 46718556)
73. H. Leveau, and J.R. van der Meer The tfdR gene product can successfully take over the role of the insertion element-inactivated TfdT protein as a transcriptional activator of the tfdCDEF gene cluster, which encodes chlorocatechol degradation in Ralstonia eutropha JMP134(pJP4) J. Bacteriol. 178 1996 6824 6832
74. A. Pohlmann, W.F. Fricke, F. Reinecke, B. Kusian, H. Liesegang, R. Cramm, T. Eitinger, C. Ewering, M. Potter, E. Schwartz, A. Strittmatter, I. Voss, G. Gottschalk, A. Steinbuchel, B. Friedrich, and B. Bowien Genome sequence of the bioplastic-producing "Knallgas" bacterium Ralstonia eutropha H16 Nat. Biotechnol. 24 2006 1257 1262 (Pubitemid 44564772)
75. M.T. Holden, H.M. Seth-Smith, L.C. Crossman, M. Sebaihia, S.D. Bentley, A.M. Cerdeno-Tarraga, N.R. Thomson, N. Bason, M.A. Quail, S. Sharp, I. Cherevach, C. Churcher, I. Goodhead, H. Hauser, N. Holroyd, K. Mungall, P. Scott, D. Walker, B. White, H. Rose, P. Iversen, D. Mil-Homens, E.P. Rocha, A.M. Fialho, A. Baldwin, C. Dowson, B.G. Barrell, J.R. Govan, P. Vandamme, C.A. Hart, E. Mahenthiralingam, and J. Parkhill The genome of Burkholderia cenocepacia J2315, an epidemic pathogen of cystic fibrosis patients J. Bacteriol. 191 2009 261 277
76. J.H. Leveau, and S. Gerards Discovery of a bacterial gene cluster for catabolism of the plant hormone indole 3-acetic acid FEMS Microbiol. Ecol. 65 2008 238 250 (Pubitemid 351989222)
77. W.M. Chen, C.H. Wu, E.K. James, and J.S. Chang Metal biosorption capability of Cupriavidus taiwanensis and its effects on heavy metal removal by nodulated Mimosa pudica J. Hazard Mater. 151 2008 364 371 (Pubitemid 351179017)
78. J.S. Zhao, D. Manno, and J. Hawari Regulation of hexahydro-1,3,5- trinitro-1,3,5-triazine (RDX) metabolism in Shewanella halifaxensis HAW-EB4 by terminal electron acceptor and involvement of c-type cytochrome Microbiology 154 2008 1026 1037 (Pubitemid 351736260)
79. J.S. Zhao, D. Manno, C. Leggiadro, D. O'Neil, and J. Hawari Shewanella halifaxensis sp. nov., a novel obligately respiratory and denitrifying psychrophile Int. J. Syst. Evol. Microbiol. 56 2006 205 212 (Pubitemid 43125918)
80. R. Papa, E. Parrilli, and G. Sannia Engineered marine Antarctic bacterium Pseudoalteromonas haloplanktis TAC125: a promising micro-organism for the bioremediation of aromatic compounds J. Appl. Microbiol. 106 2009 49 56
81. C. Medigue, E. Krin, G. Pascal, V. Barbe, A. Bernsel, P.N. Bertin, F. Cheung, S. Cruveiller, S. D'Amico, A. Duilio, G. Fang, G. Feller, C. Ho, S. Mangenot, G. Marino, J. Nilsson, E. Parrilli, E.P. Rocha, Z. Rouy, A. Sekowska, M.L. Tutino, D. Vallenet, G. von Heijne, and A. Danchin Coping with cold: the genome of the versatile marine Antarctica bacterium Pseudoalteromonas haloplanktis TAC125 Genome Res. 15 2005 1325 13235
82. R. van Der Geize, G.I. Hessels, R. van Gerwen, J.W. Vrijbloed, P. van Der Meijden, and L. Dijkhuizen Targeted disruption of the kstD gene encoding a 3-ketosteroid Δ(1)-dehydrogenase isoenzyme of Rhodococcus erythropolis strain SQ1 Appl. Environ. Microbiol. 66 2000 2029 2036 (Pubitemid 30253728)
83. R. van der Geize, G.I. Hessels, R. van Gerwen, P. van der Meijden, and L. Dijkhuizen Unmarked gene deletion mutagenesis of kstD, encoding 3-ketosteroid Δ1-dehydrogenase, in Rhodococcus erythropolis SQ1 using sacB as counter-selectable marker FEMS Microbiol Lett. 205 2001 197 202 (Pubitemid 34031920)
84. R. van der Geize, G.I. Hessels, R. van Gerwen, P. van der Meijden, and L. Dijkhuizen Molecular and functional characterization of kshA and kshB, encoding two components of 3-ketosteroid 9α-hydroxylase, a class IA monooxygenase, in Rhodococcus erythropolis strain SQ1 Mol. Microbiol. 45 2002 1007 1018 (Pubitemid 35007444)
85. R. van der Geize, G.I. Hessels, and L. Dijkhuizen Molecular and functional characterization of the kstD2 gene of Rhodococcus erythropolis SQ1 encoding a second 3-ketosteroid Δ(1)-dehydrogenase isoenzyme Microbiology 148 2002 3285 3292 (Pubitemid 35243728)
86. R. van der Geize, G.I. Hessels, M. Nienhuis-Kuiper, and L. Dijkhuizen Characterization of a second Rhodococcus erythropolis SQ1 3-ketosteroid 9α-hydroxylase activity comprising a terminal oxygenase homologue, KshA2, active with oxygenase-reductase component KshB Appl. Environ. Microbiol. 74 2008 7197 7203 (Pubitemid 352773596)
87. D. Skowasch, E. Mobus, and E. Maser Identification of a novel Comamonas testosteroni gene encoding a steroid-inducible extradiol dioxygenase Biochem. Biophys. Res. Commun. 294 2002 560 566 (Pubitemid 34694045)