Recent advances in applied and mechanistic aspects of the enzymatic hydroxylation of steroids by whole-cell biocatalysts

Steroids

Volumn 64, Issue 3, 1999, Pages 178-186

  Holland, Herbert L ^a  

^a BROCK UNIVERSITY   (Canada)

Author keywords

Enzyme; Hydroxylation; Microorganism; Steroid

Indexed keywords

STEROID;

BIOTECHNOLOGY; CATALYSIS; ENZYME MECHANISM; NONHUMAN; REVIEW; STEREOCHEMISTRY; STEROID HYDROXYLATION;

CATALYSIS; HYDROXYLATION; STEROID HYDROXYLASES; STEROIDS;

EID: 0032983057     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(98)00085-3     Document Type: Review

References (60)

1. Holland HL. Hydroxylation and dihydroxylation. In: Rehm H-J, Reed G, Kelly DR, editors. Biotechnology, Vol. 8a: Biotransformations I. Weinheim: Wiley-VCH, 1998, pp. 475-533.
2. Mahato SB, Subhadra G. Advances in microbial steroid biotransformation. Steroids 1997;62(4):332-45.
3. Farooq A, Hanson JR, Iqbal Z. Hydroxylation of progesterone by Cephalosporium aphidicola. Phytochemistry 1994;37(3):723-6.
4. Jai T, Schneider B, Adam G. Metabolic conversion of 24-epibrassinolide into pentahydroxylated brassinosteroid glucosides in tomato cell cultures. Phytochemistry 1995;40:443-8.
5. Hamada H, Konishi H, Williams HJ, Scott AI. Biotransformation of testosterone isomers by a green cell suspension culture of Marchantia polymorpha. Phytochemistry 1991;30(7):2269-70.
6. Fiorentino A, Pinto G, Pollio A, Previtera L. Biotransformation of 5α-androstane-3,17-dione by microalgal cultures. Bioorg Med Chem Lett 1991;1(12):673-4.
7. Arison BH, Carlin JR, Venkataramani S. Manufacture of testosterone 5-α reductase inhibitors with Selenastrum capriconutum. U.S. Patent 5,215,894 (1 June), 1993.
8. Xiong A, Fa Y. Microbial transformation conditions of ursodeoxychloic acid and its preparation. Weishengwu Xuebao 1995;35:204-8.
9. 4-3-ketosteroids by the fungus Rhizopus arrhizus. Acc Chem Res 1983;17:398-402.
10. Wang KC, Wang P-H, Lee S-S. Microbial transformation of protopanaxadiol and protopanaxatriol derivatives by Mycobacterium sp. (NRRL B-3805). J Nat Prod 1997;60(12):1236-41.
11. Atta-ur-Rahman, Choudhary MI, Shaheen F, Ashraf M, Jahan S. Microbial transformations of hypolipemic E-guggulsterone. J Nat Prod 1998;61(4):428-31.
12. Holland HL, Lakshmaiah G, Ruddock PL. Microbial hydroxylation of acetylaminosteroids. Steroids 1998;63(9):484-95.
13. Holland HL, Lakshmaiah G. Microbial hydroxylation of 2-oxatestosterone. J Mol Cat B:Enzymatic 1998;6:83-8.
14. Hanson JR, Nasir H. The biotransformation of some steroids by Cephalosporium aphidicola. Phytochemistry 1993;33(4):831-4.
15. Voigt B, Porzel A, Naumann H, Hörhold-Schubert C, Adam G. Hydroxylation of the native brassinosteroids 24-epicastasterone and 24-epibrassinolide by the fungus Cunninghamella echinulata. Steroids 1993;58:320-3.
16. Biton J, Azerad R, Marchandeau J-P, Lacroix I. Process for the production of new 1- or 6-hydroxylated steroids and their use as medicaments. Eur. Patent 8 1998:08845.
17. 5-3ß-hydroxysteroids by Circinella sp. Mold Russ Chem Bull 1994;43(4):689-95.
18. Voishvillo NE, Turuta, AM, Kamernitsky AV. Microorganisms as reagents for transformation of 5α-steroids. Russ Chem Bull 1994; 43(4):515-37.
19. Voishvillo NE, Istomina ZI, Kamernitsky AV, Vesela IV, Reshetova IG, Strelkova OG. Screening of microorganisms able to perform 9α-hydroxylation of 3ß-hydroxysteroids. Prikl Biokhim Mikrobiol 1994;30:617-23.
20. Hu S, Genain G, Azerad R. Microbial transformations of steroids: contribution to 14α-hydroxylations. Steroids 1995;60:337-52.
21. Omura S, Sasaki J, Mikami A, Mizogami K. Manufacture of hydroxyvitamin D with Amycolata species. Jap. Patent 02,231,089 (13 Sep.), 1991.
22. 3 using Amycolata sp. Strains Appl Microbiol Biotechnol 1992;38:152-7.
23. 3. J Ferment Bioeng 1994;78(5):380-2.
24. Hu S, Tian X, Sun, Y, Han G. Microbial hydroxylation of 13-ethyl-17ß-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one. Steroids 1996;61(7):407-10.
25. Hu S, Tian X, Han G. Microbial hydroxylation of 13-ethyl-17ß-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one. Steroids 1998;63: 88-92.
26. Chincholkar SB. Steroid biotransformations with free and immobilized cells. Microb Biotechnol 1997:7-11.
27. Holland HL, Poddar S, Tripet B. Effect of cell immobilization and organic solvents on sulfoxidation and steroid hydroxylation by Mortierella isabellina. J Ind Microbiol 1992;10:195-7.
28. Schloser D, Irrgang S, Schmauder H-P. Fermentation kinetics of free and immobilised Penicillium raistrickii able to perform the 15α-hydroxylation of 13-ethyl-gon-4-ene-3,17-dione. Acta Biotechnol 1995;15(2):161-72.
29. Vidyarthi AS, Nagar SJ. Immobilized fungal spores for microbial transformation of steroids: 11α-hydroxylation of progesterone. Biol. Memoirs 1994;20(1):15-9.
30. Dutta TK, Samanta TB. Novel catalytic activity of immobilized spores under reduced water activity. Bioorg Med Chem Lett 1997; 7(5):629-32.
31. Wang J, Chen C, Li B, Zhang J, Yu, Y. Production of hydrocortisone from cotexolone-21-acetate by immobilized Absidia orchidis in cosolvent-containing media. Enzyme Microb Technol 1998;22(5):368-73.
32. van den Brink HJM, van Gorcom RFM, van den Hondel CAMJJ, Punt PJ. Cytochrome P-450 enzyme systems in fungi. Fungal Gen Biol 1998;23(1):1-17.
33. Smith KE, Latif SA, Kirk DN. Microbial transformations of steroids - VII. Hydroxylation of progesterone by extracts of Phycomyces blakesleeanus. J Steroid Biochem Mol Biol 1991;38(2):249-56.
34. Madyashta KM, Joseph T. Studies on the 14α-hydroxylation of progesterone in Mucor piriformis. J Steroid Biochem Mol Biol 1993; 45(6):563-9.
35. Nega E, Grunwaldt G. Evidence for and characterization of cytochrome P-450 in Neurospora crassa. J Basic Microbiol 1997;37(2): 139-45.
36. Mutafov S, Angelova B, Avramova T, Boyadjieva L, Dimova I. The inducibility of 9α-steroid hydroxylating activity in resting Rhodococcus sp. cells. Process Biochem 1997;32(7):585-9.
37. Vitas M, Rozman D, Komel R, Kelly SL. P450-mediated progesterone hydroxylation in Cochliobolus lunatus. J Biotechnol 1995;42: 145-50.
38. Vitas M, Pajic T, Kelly SL, Komel R. 11ß-Hydroxysteroid dehydrogenase activity in progesterone biotransformation by the filamentous fungus Cochliobolus lunatus. J Steroid Biochem Mol Biol 1997;63(4-6):345-50.
39. Ahmed F, Williams RAD, Smith KE. Microbial transformations of steroids - X. Cytochromes P-450 11α-hydroxylase and C17-C20 lyase and A 1-ene dehydrogenase transform steroids in Nectria haematococca. J Steroid Biochem. Mol Biol 1996;58(3):337-49.
40. Cotillon A-C, Doostzadeh J, Morfin R. The inducible and cytochrome P450-containing dehydroepiandrosterone 7α-hydroxylating enzyme system of Fusarium moniliforme. J Steroid Biochem Mol Biol 1997; 62(5-6):467-75.
41. Irrgang S, Schlosser D, Fritsche W. Involvement of cytochrome P-450 in the 15α-hydroxylation of 13-ethyl-gon-4-ene-3,17-dione by Penicillium raistrickii. J Steroid Biochem Mol Biol 1997;60(5-6): 339-46.
42. Shet MS, Fisher CW, Estabrook RW. The function of recombinant cytochrome P450s in intact Escherichia coli cells: the 17α-hydroxylation of progesterone and pregnenolone by P450c17. Arch Biochem Biophys 1997;339(1):218-25.
43. Nishihara H, Okamura T, Schmid RD, Hauck A, Reuß M. Biotechnological potential of P450 monooxygenases. High-level production of bovine cytochrome P450c17 monooxygenase during medium cell density culture of a recombinant yeast, Saccharomyces cerevisiae GRF 18 (Yep-Tokul). J Biotechnol 1997;56:57-61.
44. Slijkhuis H, Selten GCM, Smaal EB. Multiple oxidation of steroids with genetically engineered cells. PCT Int. Appl. WO 90 03,428 (5 April), 1990.
45. C24-producing Escherichia coli. Japan Pat. 06,205,685 (26 July) 1994.
46. Mehmood Z, Kelly DE, Kelly SL. Progesterone biotransformations by human P4503A4 in yeast. Biotechnol Lett 1995;17(1):83-8.
47. Teixeira J, Gil G. Cloning, expression, and regulation of lithocholic acid 6ß-hydroxylase. J Biol Chem 1991;266(31):21030-6.
48. Cali JJ, Russell DW. Characterization of human sterol 27-hydroxylase. J Biol Chem 1991;266(12):7774-8.
49. Doehmer J, Wölfel C, Dogra S, Doehmer C, Seidel A, Platt KL, Oesch F, Glatt HR. Applications of stable V79-derived cell lines expressing rat cytochromes P4501A1, 1A2, and 2B1. Xenobiotica 1992;22(9-10):1093-9.
50. Holland HL. Investigation of the carbon- and sulfur-oxidising capabilities of microorganisms by active-site modelling. Adv Appl Microbiol 1997;44:125-65.
51. d by mutations at putative distal site. Chem Lett 1991:973-6.
52. Halpert JR, He Y. Engineering of cytochrome P450 2B1 specificity. J Biol Chem 1993;268(6):4453-7.
53. Iwasaki M, Darden TA, Parker CE, Tomer KB, Pedersen LG, Negishi M. Inherent versatility of P-450 oxygenase. J Biol Chem 1994; 269(12):9079-83.
54. Iwasaki M, Davis DG, Darden TA, Pedersen LG, Negishi M. Multiple steroid-binding orientations: alteration of regiospecificity of dehydroisoandrosterone 2- and 7-hydroxylase activities of cytochrome P-450 2a-5 by mutation of residue 209. Biochem J 1995;306:29-33.
55. Iwasaki M, Darden TA, Pedersen LG, Negishi M. Altering the regiospecificity of androstenedione hydroxylase activity in P45s 2a-4/5 by mutation of the residue at position 481. Biochemistry 1995;34(15): 5054-9.
56. He YQ, Szklarz GD, Halpert JR. Interconversion of the androstenedione hydroxylase specificities of cytochrome P450 2B4 and 2B5 upon simultaneous site-directed mutagenesis of four key substrate recognition residues. Arch Biochem Biophys 1996;335(1):152-60.
57. He YQ, Harlow GR, Szklarz GD, Halpert JR. Structural determinants of progesterone hydroxylation by cytochrome P450 2B5: the role of nonsubstrate recognition site residues. Arch Biochem Biophys 1998; 350(2):333-9.
58. Breslow R, Zhang X, Huang Y. Selective catalytic hydroxylation of a steroid by an artificial cytochrome P-450 enzyme. J Am Chem Soc 1997;119(19):4535-6.
59. Breslow R, Huang Y, Zhang X, Yang J. An artificial cytochrome P450 that hydroxylates unactivated carbons with regio- and stereoselectivity and useful catalytic turnovers. Proc Natl Acad Sci USA 1997;94(21):11156-8.
60. Breslow R, Gabriele B, Yang J. Geometrically directed selective steroid hydroxylation with high turnover by a fluorinated artificial cytochrome P-450. Tetrahedron Lett 1998;39(19):2887-90.