Advances in microbial steroid biotransformation

Steroids

Volumn 62, Issue 4, 1997, Pages 332-345

  Mahato, Shashi B ^a   Garai, Subhadra ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

compilation; melabolite; microbial biotransformation; review; substrate

Indexed keywords

CYCLODEXTRIN;

BACTERIAL METABOLISM; BIOTRANSFORMATION; CATALYSIS; COST CONTROL; FERMENTATION; GENETIC ENGINEERING; HYDROXYLATION; IMMOBILIZED CELL; REVIEW; STEROID METABOLISM;

ACETONE; BACTERIA; BIOTRANSFORMATION; CARBON; CATALYSIS; CYCLODEXTRINS; CYTOLOGICAL TECHNIQUES; FERMENTATION; FUNGI; HYDROXYLATION; MODELS, CHEMICAL; STEROIDS;

BACTERIA (MICROORGANISMS);

EID: 0030896478     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(96)00251-6     Document Type: Review

References (133)

1. Murray HC, Peterson DH (1952). Oxygenation of steroids by Mucorales fungi. U.S. Patent 2602769 (Upjohn Co., Kalamazoo, Michigan, USA).
2. Mahato SB, Mukherjee A (1984). Steroid transformations by microorganisms. Phytochemistry 23:2131-2154.
3. Mahato SB, Banerjee S (1985), Steroid transformation by microorganisms II. Phytochemistry 24:1403-1421.
4. Mahato SB, Banerjee S, Podder S (1989). Steroid transformations by microorganisms III. Phytochemistry 28:7-40.
5. Mahato SB, Mazumder I (1995). Current trends in microbial steroid biotransformation. Phytochemistry 34:883-898.
6. Chincholkar SB, Sukhodol'skaya GV, Baklashova TG, Koschcheenko KA (1992). Peculiarities of the 11β-hydroxylation of steroid compounds by the mycellium of Curvularia lunata VKMF-644 in the presence of β-cyclodextrin. Prikl Biokhim Mikrobiol 28:685-693.
7. Dtugonski J, Bartnicku K, Choyeeka V, Sedlaezek L (1992). Stabilization of steroid 11-hydroxylation activity of Cunninghamella elegans protoplasts in organic osmotic stabilizers. World J Microbiol Biotechnol 8:500-504.
8. Yoshioka H, Asada S (1994). 14α-Hydroxy-4-androstene-3,17-dione manufacture with Myrothecium. Japanese Patent 06, 153, 987 (Nippon Kayaku, KK).
9. Asada S (1994). Microbial manufacture of 14α-hydroxy-4-androstene-3,17-dione. Japanese Patent 06, 225, 791 (Nippon Kayaku, KK).
10. Yoshioka H, Asada H, Fujita S (1994). Process for production of 6β, 14α-dihydroxy-4-androstene-3,17-dione. European Patent 599, 658 (Nippon Kayaku, KK).
11. Nakakoshi M, Yoshihama M, Nakamura H, Kumazawa E, Kabayashi N, Kawashima T, Ishiguro S, Seya M (1993). Preparation of 14α-hydroxy-4-androstene-3,6,17-trione from 4-androstene-3,17-dione. Japanese Patent 0576, 387 (Snow Brand Milk Prod. Co. Ltd., Tokyo).
12. Birke M, Hoerhold C, Groh H. Deppmeyer V, Naumann H, Schildbatch A, Daehnhardt S, Schaner F (1992). Microbial manufacture of 9α-hydroxyandorst-4-ene-3,17-dione from sterols. (East) German Patent 298, 278 (Jena Pharm. Gmbh., Jena).
13. Birke M, Schildbach A, Heller I, Hoerhold C, Seidel L, Atart P (1992). Microbial manufacture and recovery of 9α-hydroxyandrost-4-ene-3,17-dione. (East) German Patent 298, 279 (Jena Pharm. Gmbh., Jena).
14. 4-3-keto-9α-hydroxy derivatives. Khim-Farm Zh 26:64-68.
15. Borman EA, Redikulifsev Yu V, Koshcheenko KA, Turuta AM, Kamernitskii AV (1992). Transformation of sitosterol to 9α-hydroxy-androstene-dione by Microbacterium sp. 207 cells in the presence of an adsorption resin. Prikl Biokhim Mikrobiol 28:551-556.
16. Reiche R, Heller I, Hoerhold C, Gotlsehaldf B (1992). Manufacture of androsta-1,4-diene-3,17-dione from sterols with Mycobacterium. (East) German Patent 300, 364 (VEBJENA PHARM).
17. Liu WH, Kuo CW, Wu KL, Lee CY, Hsu WY (1994). Transformation of cholesterol to testosterone by Mycobacterium sp. J Ind Microbiol 13:167-171.
18. Hung B, Falero A, Lianes N, Perez C, Ramirez MA (1994). Testosterone as biotransformation product in steroid conversion by Mycobacterium sp. Biotechnol Lett 16:497-500.
19. Spassov G, Pramatarova V, Vlahov R, Reinhold G (1993). Bioconversion of sitosterol to androstene-dione by mutants of Mycobacterium vaccae. Dokl Bulg Acad Nauk 46:123-126.
20. Lee CY, Chen CD, Liu WH (1993). Production of androsta-1,4-diene-3,17-dione from cholesterol using two-step microbial transformation. Appl Microbiol Biotechnol 38:447-452.
21. Ghanem KM, Yusef HH (1992). Transformation of Reichstein's compound S into prednisolone by a mixed culture under some physiological conditions. Rev Latinoam Microbiol 34:107-114.
22. Ghanem KM, Yusef HH (1992). Some nutritional requirements of a mixed culture transforming Reichstein's compound S into prednisolone. Can J Microbiol 38:753-757.
23. Ghanem KM, EL-Aassar SA, Yusef HH (1992). Transformation of Reichstein's compound S into prednisolone by immobilized mixed cultures. J. Chem Technol Biotechnol 54:115-121.
24. Klibanov AM (1986). Enzymes that work in organic solvents, Chemtech 16:354-359.
25. Halling PJ (1987). Biocatalysis in multiphase reaction mixtures containing organic liquids. Biotechnol Adv 5:47-84.
26. Zaks A, Klibanov AM (1985). Enzyme-catalyzed processes in organic solvents. Proc Natl Acad Sci USA 82:3192-3196.
27. Zaks A, Klibanov AM (1988). The effect of water on enzyme action in organic media. J Biol Chem 263:8017-8021.
28. Sakuvai T, Margolin AL, Rkussell AJ, Klibanov AM (1988). Control of enzyme enantioselectivity by the reaction medium. J Am Chem Soc 110:7236-7237.
29. Holland HL, Poddar S, Tripet B (1992). Effect of cell immobilization and organic solvents on sulfoxidation and steroid hydroxylation by Mortierella isabellina. J Ind Microbiol 10:195-197.
30. Ahmad S, Garg SK, John BN (1992). Biotransformation of sterols: Selective cleavage of the side chain. Biotechnol Adv 10:1-67.
31. Dias ACP, Cabrai JMS, Pinheiro HM (1994). Sterol side-chain cleavage with immobilized Mycobacterium cells in water immiscible organic solvents. Enzyme Microb Technol 16:708-714.
32. Miethe P, Gruber R, Mohr KH (1992). Lyotropic liquid crystals - A new possibility of biocatalysis in organic media. Bioengineering 8:38-41.
33. Oda S, Ohta H (1992). Microbial transformation on interface between lyophilic carriers and hydrophobic organic solvents. Biosci Biotechnol Biochem 56:2041-2045.
34. Jadoun J, Bar R (1993). Microbial transformations in a cyclodextrin medium. Part 3. Cholesterol oxidation by Rhodococcus erythropolis. Appl Microbiol Biotechnol 40:230-240.
35. Jadoun J, Bar R (1993). Microbial transformation in a cyclodextrin medium. Part 4. Enzyme vs Microbial oxidation of cholesterol. Appl Microbial Biotechnol 40:477-482.
36. Alekhina TM, Ryzhkova VM, Gusarova TI, Kurakov VV, Klabnichkina GA (1993). Microbial transformation of steroid β-cyclodextrin inclusion compounds. Khim-Farm Zh 27:59-62.
37. Uden WV, Woeydenbag H, Prar N (1994). Cyclodextrin as a useful tool for the bioconversion in plant cell biotechnology. Plant Cell Tissue Organ Cult 38:103-113.
38. Banerjee S, Mukherjee E, Mahato SB (1993). Metabolism of androst-4-ene-3,17-dione by Aspergillus fumigatus. J Chem Res (Suppl): 236-237.
39. Garai S, Banerjee S, Mahato SB (1995). Selective 1-dehydrogenation of progesterone by Aspergillus fumigatus. J Chem Res (Suppl): 408-409.
40. Houng JY, Chiang WP, Chen KC, Tiu C (1994). 11α-Hydroxylation of progesterone in bi-phasic media using alginate-entrapped Aspergillus ochraceus gel beads coated with polyurea. Enzyme Microb Technol 16:485-491.
41. Murohisa T, Iida M (1993). Studies on microbial transformation (XXVI). Microbial degradation of 19-hydroxysterol side-chains. J Ferment Bioeng 75:13-17.
42. Krischenoski D, Kieslich K (1993). Two novel microbial conversion products of progesterone derivatives. Steroids 58:278-281.
43. Sankar VN, Row TNG, Madyastha KM (1993). Evidence for a new pathway in the microbial conversion of 3β-acetoxycholest-5-en-19-ol into estrone. J Chem Soc Perkin Trans 1:2233-2236.
44. Murohisa T, Iida M (1993). Studies on microbial transformation (XXVII). Some new intermediates in microbial side-chain degradation. J Ferment Bioeng 76:174-177.
45. Yoshihama M (1993). Microbial hydroxylation of steroid hormones and their pharmaceutical applications. Yukijirushi Nyugyo Kenkyusho Hokoku 99:1-70.
46. Mahato SB, Mukherjee E, Banerjee S (1994). Pharmaceutically important steroids by microbial biotransformations with Aspergillus fumigatus. Proceedings of the 16th International Congress of Biochemistry and Molecular Biology, New Delhi, India, Abstracts, Vol II. p. 150.
47. Yoshihama M, Tamura K, Miyata N, Nakakoshi M (1988). Manufacture of 7β-hydroxy-4-pregnene-3,20-dione derivatives from pregn-4-ene-3,20-dione with Acremonium. World Patent 8805, 782 (Snow Brand Milk Products Co. Ltd).
48. Madyastha KM, Joseph T (1994). Transformation of 16-dehydroprogesterone and 17α-hydroxyprogesterone by Mucor piriformis. Appl Microbiol Biotechnol 41:170-177.
49. Dastidar P, Joseph T, Madyastha KM, Row TNG (1993). Structure of a steroid fungal metabolite. Acta Cryst Sect C: Cryst Structure Commun C49:273-215.
50. Nihira T, Okada Y, Yamada Y (1992). A new bile acid glycoside produced by Cunninghamella blakesleeana ST-22 from lithocholic acid. J Ferment Bioeng 74:191-193.
51. Ambrus G. Iikoy E, Horvath G, Podauyi B, Bocskei Z, Gyurky S, Jekkel A (1992). Novel intermediates of microbial side-chain degradation of sitosterol. Tetrahedron Lett 33:5267-5268.
52. Mukherjee E, Banerjee S, Mahato SB (1993). Transformation of cholic acid by Arthrobacter simplex. Steroids 58:484-490.
53. Mahato SB, Mukherjee E, Banerjee S (1994). Advances in microbial biotechnology of bile acids. Biotech Adv 12:357-391.
54. Mahato SB, Mazumder I, Luger P, Weber M (1994). Cholic acid induced N-methylhydantoin synthesis in microbial system. J Indian Chem Soc 71:401-408.
55. Kominek LA, Wolf JH, Steiert PS (1993). 1,2-dehydrogenation of steroidal 21-esters with Arthrobacter simplex, or, Bacterium cyclooxidans. U.S. Patent 5, 225, 335 (Upjohn Co.).
56. Zeng B, Chen S, Chen B (1993). Improvement of enzyme activity in microbial 11β-hydroxylation of steroids. Zhongguo Yiyao Gongye Zazhi 24:529-532.
57. Undisz K, Groh H, Stopsach H, Hoerhold SC (1992). Bioconversion of steroids by Cochliobolus lunatus. II. 11β-Hydroxylation of 17α,21-dihydroxypregna-1,4-diene-3,20-dione-17-acetate in dependence of the inducer structure. J Steroid Biochem Mol Biol 43:543-547.
58. Hanson JR, Nasir H (1993). The biotransformation of some steroids by Cephalosporium aphidicola, Phytochemistry 33:831-834.
59. Shi J, Sun X, Zhen L, Niu J (1993). 11α-Hydroxylation of androsta-1,4-diene-3,17-dione (ADD) by Aspergillus ochraceus. Shanghai Yike Daxue Xuebao 20:373-376.
60. Weber A, Kewnnecke M (1993). Preparation of 14α-hydroxy-4-androstene-3,17-dione by fermentation. German Patent 4,129,005 (Schering A, G).
61. Madyastha KM (1994). Preparatively useful transformation of steroids and morphine alkaloids by Mucor piriformis. Proc Indian Acad Sci Chem Sci 106:1203-1212.
62. Arison BH, Carlin JR, Venkataramant ES (1993). Manufacture of testosterone-5α-reductase inhibitors with Selenastrum capricornutum. U.S. Patent 5, 215, 894 (Merck).
63. Santhanam HK, Shreke GS (1994). Solvent selection and productivity in multiphase biotransformation systems, Biotechnol Prog 10:187-192.
64. Sedlaczek L, Milczarek K, Wilmanska D, Pamiewski P, Lubisz K, Filip A, Majdziak K, Szczepaniak J, Korbel J (1993). Method for manufacturing hydrocortison from Reichstein's S substance. Poland Patent 161, 090 (Pabianickie Zaklady Farmaceutyczne "Polfa").
65. Wilzmanska D, Milczarek K, Rumijowksa A, Bartnicka K, Sedlaczek L (1992). Elimination of byproducts in 11β-hydroxylation of substance S using Curvularia lunata clones regenerated from NTG-treated protoplasts. Appl Microbiol Biotechnol 37:626-630.
66. Zeng B, Zhang B (1992). The relationship between the growing characterization and steroid 11α-hydroxylation of Beauveria bassiana AS69 during fermentation. Weishengwuzue Zazhi 12:43-45.
67. Voigt B, Porzel A, Naumann H, Hoerhold SC, Adam G (1993). Hydroxylation of the native brassinosteroids 24-epicastasterone and 24-epibrassinolide by the fungus Cunninghamella echinulata. Steroids 58:320-323.
68. Schmauder HP, Irrgang S, Schlosser D (1991). Steroid hydroxylation with an immobilized filamentus fungus. Meded Fac Landbouwwet, Rijksuniv Gent 56:1785-1787.
69. Schlosser D, Irrgang S, Schmauder HP (1992). Immobilization of Penicillium raistrickii spores and mycellium growth for 15α-hydroxylation of 13-ethylgon-4-ene-3,17-dione. Folia Microbial (Prague) 37:249-255.
70. Schlosser D, Schmauder HP (1992). Catalyst capacity factor in steroid biotransformation. Chem Eng Tech 64:357-360.
71. Schlosser D, Irrgang S, Schmauder HP (1993). Steroid hydroxylation with free and immobilized cells of Penicillium raistrickii in the presence of β-cyclodextrin. Appl Microbiol Biotechnol 39:16-20.
72. Schlosser D, Irrgang S, Schmauder HP, Dautzenberg H, Tomaschewski G, Zimelka W, Baumgartl H (1992). 15α-Hydroxylation of 13-ethyl-gon-4-ene-3,17-dione with free and immobilized Penicillium raistrickii. Proceedings of the DECHEMA Biotechnol Conference, 231-234.
73. Madyastha KM, Joseph T (1993). Studies on the 14α-hydroxylation of progesterone in Mucor piriformis. J Steroid Biochem Mol Biol 45:563-569.
74. Hamada H, Takiguchi K, Konishi H (1992). Manufacture of 6β-hydroxytestosterone from testosterone by plant tissue culture of Marchantia. Japanese Patent 04, 139, 193 (JGC Corp.).
75. Farooq AH, James R, Iqbal Z (1994). Hydroxylation of progesterone by Cephalosporium aphidicola. Phytochemistry 37:723-726.
76. Kim MH, Kim MN (1991). Transformation pathway of the progesterone by Rhizopus nigricans. Misaengmul Hakhoechi 29:111-116.
77. Dutta TK, Samanta TB (1992). An improved method for separation and estimation of bioconverted steroids. J Gen Appl Microbiol 38:283-288.
78. Lee JJ, Kim MN (1993). Ion effect on steroid bioconversion in Rhizopus nigricans Han'guk kyunhakhoechi 21:23-27.
79. Vitas M, Smith K, Rozman D, Komel R (1994). Progesterone metabolism by the filamentous fungus Cochliobolus lunata. J Steroid Biochem Mol Biol 49:87-92.
80. Smith KE, Ahmed F, Williams RAD, Kelly SL (1994). Microbial transformations of steroids, VIII. Transformation of progesterone by whole cells and microsomes of Aspergillus fumigatus. J Steroid Biochem Mol Biol 49:93-100.
81. Chen KC, Yin Ws, Tiu C, Houng JY (1994). 11α-Hydroxylation of progesterone using modified alginate immobilized cells. Enzyme Microbiol Technol 16:551-555.
82. Atta FM, El-kady IA (1994). Transformation of progesterone by Cochliobolus spicifer. Bull Fac Sci, Assiut Univ, B23:83-91.
83. Pollio A, Pinto G, Greca MD, De Mario A, Previtera L (1994). Progesterone bioconversion by microalgal cultures, Phytochemistry 37:1269-1272.
84. Madyastha KM, Shankar VN (1994). Role of neutral metabolites in microbial conversion of 3β-acetoxy-19-hydroxycholest-5-ene into estrone. Appl Environ Microbiol 60:1500-1511.
85. Liu W, Lee CY (1992). Production of androst-4-ene-3,17-dione from cholesterol by Mycobacterium sp. in a synthetic medium. Zhongguo Nongye Hyaxue Huizhi 30:52-58.
86. Shi J, Chu Z, Ju Y, Mo G, Cheng W (1992). Degradation of cholesterol to androsta-1,4-diene-3,17-dione by Rhodococcus corallina. Zhongguo Yiyao Gongye Zazhi 23:204-207.
87. Ahmed S, Roy PK, Basu SK (1993). Cholesterol side-chain cleavage by immobilized cells of Rhodococcus equi DSM 89-133. Indian J Exp Biol 31:319-322.
88. Smith M, Zahnley J, Pfeifer D, Goff D (1993). Growth and cholesterol oxidation by Mycobacterium species in Tween 80 medium. Appl Environ Microbiol 59:1425-1429.
89. Srivastava A, Patil S (1994). Investigation of some physicochemical parameters involved in the biotransformation of cholesterol to 17-ketosteroids. J Microb Biotechnol 9:101-112.
90. Ahmed S, Johri BN (1993), Microbial transformation of steroids in organic media. Indian J Chem (sect B) 32B:67-69.
91. Vorbrodt HM, Adam G, Porzel A, Hoerhold C, Daenhardt S, Boehme KH (1991). Microbial degradation of 2α,3α-dihydroxy-5α-cholestan-6-one by Mycobacterium vaccae. Steroids 56:586-588.
92. Wang KC, Chiang N, Su CC, (1994). Microbial transformation of 5β-steroids with Mycobacterium sp. (NRRLB-3805). Chin Pharm J (Taipei) 46:227-232.
93. Weber A, Kennecke M, Neef G (1992). 20-Methyl-5,7-pregnadiene-3β,21-diol derivatives and their manufacture with Mycobacterium. World Patent 0903, 465 (Schering A-G).
94. 20 bond in pregnane by a Pseudomonas sp. J Steroid Biochem Mol Biol 44:101-104.
95. Dutta RK, Roy M, Singh HD (1992). Metabolic blocks in the degradation of β-sitosterol by a plasmid-cured strain of Arthrobacter oxydans. J Basic Microbiol 32:167-176.
96. Roy PK, Khan AW, Kumar J, Chopra SDK, Basu SK (1992). Steroid transformation in a laboratory-scale glass airlift fermentor. World J Microbiol Biotechnol 8:399-401.
97. Mathur S, Bhatia MC, Mathur SN (1992). Biotransformation of β-sitosterol into 17-ketosteroids by some strains of Arthrobacter. Role Biotechnol Agric 99-102.
98. Kurakov VV, Korovova YN, Ryzhkova VM (1993). Effect of the initial concentration of β-sitosterol on its microbiological transformation to androst-4-ene-3,17-dione. Khim Farm Zh 27:65-67.
99. Shukla A, Patil S, Bharti S, (1992). Microbial conversion of solasodine to 4-androstene-3,17-dione (AD), a key intermediate for androgen synthesis. Lett Appl Microbiol 15:86-88.
100. Seidel L, Hoerhold C (1992). Selection and characterization of new microorganisms for the manufacture of 9-OH-AD from sterols. J Basic Microbiol 32:49-55.
101. Lee KU (1990). Conversion of plant sterol to androst-4-ene-3,17-dione by a mutant of Mycobacterium sp. NRRLB-3805. Misaengmul Hakhoechi 28:351-363.
102. Atrat PG, Koch B, Szekalla B, Hoerhold SC (1992). Application of newly synthesized detergents in the side-chain degradation of plant sterols by Myobacterium fortuitum. J Basic Microbiol 32:147-157.
103. Gottschaldt B, Grosse HH, Hoerhold C, Welzker M, Naumann H, Heller I, Birke M, Plonka G (1993). German Patent 301, 740 (Institute für Microbiologie and Experimentelle Therapie; Jenapharm GmbH JENA).
104. Oda S (1994). Manufacture of 1,4-androstadiene-3,17-dione with immobilized microorganism. Japanese Patent 0600, 095 (Kansai Paint Co. Ltd).
105. Zhang LQ, Bian EP, Wang Y (1992). Side-chain cleavage of sterols by Mycobacterium sp. M12. Yaoxye Xuebao 27:903-907.
106. Weber A, Kenneck M (1992). Manufacture of 4-pregnene-3,20-dione and its derivative by microbial transformation of pregnanes. World Patent 9203, 571 (Schering A-G).
107. 1-dehydrogenation with entrapped cells in organic medium. Biocatalysis 7:83-96.
108. Wang KC, Chaing N, Lee SS (1993). Microbial transformation of 5-α-androstan-3α-ol-17-one with Mycobacterium sp. Zhonghua Yaoxue Zazhi 45:215-221.
109. Kimura H, Okamura A, Kawaide H, Yamaura T (1992). Oxidation of bile acids with Bacillus, European Patent 518, 661 (Tokyo Tanabe Co. Ltd).
110. Kimura H, Okamura A, Kawide H (1994). Oxidation of 3,7 and 12-hydroxyl groups of cholic acid by an alkalophilic Bacillus sp. Biosci Biotechnol Biochem 58:1002-1006.
111. Panchishina MV (1992). Transformation of sterols by Escherichia. Zh Mikrobiol Epidemiol Immunobiol, 8-11.
112. Osipowicz B, Krezel Z, Siewinski A (1992). Biotransformation XXXIII. Oxidation of 3β- and 17α-hydroxysteroids by Nocardia rubra cells in heptane-water system. J Basic Microbiol 32:215-216.
113. Liu WH, Tsai MS, Lee CY (1994). Bioconversion of cholesterol to cholest-4-ene-3-one using free and immobilized growing cells of Arthrobacter simplex. Zhongguo Huaxue Huizhi 32:190-198.
114. Myamato I, Toyoda K (1994). Cholestenone manufacture with cholesterol oxidase of Rhodococcus, Japanese Patent 06, 157, 585 (Nippon Oils and Fats Co. Ltd).
115. Kimura H, Okamura A, Kawaide H (1993). Bacillus for manufacture of 3α,7α-dihydroxy-12-keto-5β-cholanic acid. European Patent 539, 216 (Tokyo Tanabe Co. Ltd).
116. Weber A, Kennecke M, Klages U, Nickisch K, Rohde R (1992). Preparation of 17-oxosteroids by microbial oxidation of 17β-hydroxysteroids. World Patent 9203, 572 (Schering A-G).
117. Sallam LA, El-Abyad MS, El-Refai AMH, El-Menofi HA, Adham NZ (1995). Bioconversion of 19-nortestosterone by Rhodococcus sp. DSM 92-344. I: Optimization of transformation parameters. Process Biochem (Oxford) 30:25-34.
118. Grigorova P, Krysteva M, Pendulovska V, Bashinovsky S, Mitova J, Krysteva S (1992). Activity of immobilized cells from Arthrobacter simplex included in polymer matrix. Tr Nauchnoizsled Khimikofarm Inst 18:94-102.
119. 1-Dehydrogenation of cortisol with bacteria II. Some aspects of the enzymic-dehydrogenation of cortisol with Corynebacterium equi. Egypt J Microbiol 28:215-222.
120. 1-Dehydrogenation of cortisol with bacteria I-screening experiments and some physiological studies. Egypt J Microbiol 28:119-130.
121. 1-dehydrogenation of steroids in organic media. Biotechnol Bioeng 40:1123-1127.
122. 1-dehydrogenation in organic media using immobilized whole cells. Prog Biotechnol 8:129-136.
123. Kimura H, Okamura A (1992). Manufacture of 3-keto-7β-hydroxycholanic acid with Bacillus. Japanese Patent 04, 278, 096 (Tokyo Tanabe Co. Ltd).
124. Hamada H, Naka S, Kurban H (1993). Stereoselective reduction in the biotransformation of androstane derivatives by cell suspension cultures of Marchantia polymorpha. Chem Lett :2111-2112.
125. Mazumder I, Mahato SB (1993). Bile acid transformation by Alcaligens recti. Steroids 58:78-86.
126. Fa Y, Su Q (1992). Microbial production of 3-oxo-bisnorchola1,4-diene-22-oic acid from cholesterol by an Arthrobacter 82. Weishengwu Xuebao 32:17-22.
127. Sugiura T, Tsuji M, Fumino M, Ichihara Y (1992). Manufacture of 3α,12α-dihydroxy-7-keto-5β-bisnorcholanic acid (salts) with Corynebacterium. Japanese Patent 04, 211, 386 (Kuraray Co. Ltd).
128. Mukherjee E, Banerjee S, Mahato SB (1993). Microbial transformation of deoxycholic acid and lithocholic acid by Arthrobacter simplex. J Chem Res (suppl): 416-417.
129. Kreis W, Reinhard E (1992). 12β-Hydroxylation of digitoxin by suspension-cultured Digitalis lunata cells, Production of digoxin in 20 lit and 300-litre air-lift bioreactors. J Biotechnol 26:257-273.
130. El Olemy MM, Elhag H, El Domiaty M, Sattar EA, Al Azizi MM, Al Said MS (1994). Biotransformation of digitoxigenin by cell suspension cultures of Pergularia tomentosa and Ammi visnaga. Saudi Pharm J 2:76-83.
131. Choudhury S, Halos S, Krischenowski D, Schmeda-Hirschmann G (1993). Two new 17α-hydroxy progesterone transformation products from Nocardia DSM 43298. World J Microbiol Biotechnol 9:56-58.
132. Weber A, Kennecke M, Vidic HJ (1993). Manufacture of 17α-hydroxy-3-methoxy-8,14-seco-1,3,5 (10),9(11) estratetraene-14-one by reduction in aqueous suspension with Kloeckera magma. World Patent 9320, 222 (Schering A-G).
133. Ionkova I (1991). Biotransformation of β-methyldigitoxin by surface cultures of Digitalis purpurea L. in vitro. Probl Farmakol Farm 5:38-43.