Engineering a hydroxysteroid dehydrogenase to improve its soluble expression for the asymmetric reduction of cortisone to 11β-hydrocortisone

Applied Microbiology and Biotechnology

Volumn 98, Issue 21, 2014, Pages 8879-8886

  Zhang, Dalong ^a   Zhang, Rui ^a   Zhang, Jie ^b   Chen, Liying ^b   Zhao, Chunxia ^b   Dong, Wenyue ^a   Zhao, Qing ^a   Wu, Qiaqing ^a   Zhu, Dunming ^a  

^a Chinese Academy of Sciences   (China)

^b Tianjin Lisheng Pharmaceutical Co Ltd   (China)

Author keywords

11 Hydrocortisone; Biocatalysis; Hydroxysteroid dehydrogenase; Whole cell biotransformation

Indexed keywords

BACTERIOLOGY; BIOCATALYSTS; CAPILLARY FLOW; CATALYSIS; CORTISOL; ESCHERICHIA COLI; MAMMALS; PROTEINS; REGIOSELECTIVITY;

ANTI-INFLAMMATORY DRUGS; ASYMMETRIC REDUCTION; BIOCATALYSIS; GLUCOSE DEHYDROGENASE; HYDROXYSTEROID DEHYDROGENASE; SOLUBLE EXPRESSION; WHOLE CELL BIOCATALYSTS; WHOLE-CELL BIOTRANSFORMATIONS;

DRUG DELIVERY;

CORTISONE; GLUCOSE DEHYDROGENASE; HYDROCORTISONE; HYDROXYSTEROID DEHYDROGENASE; MUTANT PROTEIN;

ANIMAL; BACILLUS SUBTILIS; BIOTRANSFORMATION; CHEMISTRY; ENZYMOLOGY; ESCHERICHIA COLI; GENE DELETION; GENE EXPRESSION; GENETICS; GUINEA PIG; METABOLISM; MOLECULAR CLONING; OXIDATION REDUCTION REACTION; PROTEIN ENGINEERING; SOLUBILITY;

ANIMALS; BACILLUS SUBTILIS; BIOTRANSFORMATION; CLONING, MOLECULAR; CORTISONE; ESCHERICHIA COLI; GENE EXPRESSION; GLUCOSE 1-DEHYDROGENASE; GUINEA PIGS; HYDROCORTISONE; HYDROXYSTEROID DEHYDROGENASES; MUTANT PROTEINS; OXIDATION-REDUCTION; PROTEIN ENGINEERING; SEQUENCE DELETION; SOLUBILITY;

EID: 84920258832     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-014-5967-1     Document Type: Article

References (24)

1. Chen KC, Wey HC (1990) Dissolution enzyme kinetics of 11 beta-hydroxylation of cortexolone by Curvularia lunata. Enzyme Microb Technol 12(8):616–621
2. Dlugonski J, Paraszkiewicz K, Sedlaczek L (1997) Maintenance of steroid 11-hydroxylation activity in immobilized Cunninghamella elegans protoplasts. World J Microb Biotechnol 13(4):469–473
3. Dragan CA, Zearo S, Hannemann F, Bernhardt R, Bureik M (2005) Efficient conversion of 11-deoxycortisol to cortisol (hydrocortisone) by recombinant fission yeast Schizosaccharomyces pombe. Fems Yeast Res 5(6–7):621–625
4. Elleby B, Svensson S, Wu XQ, Stefansson K, Nilsson J, Hallen D, Oppermann U, Abrahmsen L (2004) High-level production and optimization of monodispersity of 11 beta-hydroxysteroid dehydrogenase type Ι. Biochim Biophys Acta-Proteins Proteom 1700(2):199–207
5. Fline JD, van der Waard FW (1970) Process for preparation of trihydroxy steroids. US Patent 3530038
6. Hakki T, Zearo S, Dragan CA, Bureik M, Bernhardt R (2008) Coexpression of redox partners increases the hydrocortisone (cortisol) production efficiency in CYP11B1 expressing fission yeast Schizosaccharomyces pombe. J Biotechnol 133(3):351–359
7. Hosfield DJ, Wu YQ, Skene RJ, Hilgers M, Jennings A, Snell GP, Aertgeerts K (2005) Conformational flexibility in crystal structures of human 11 beta-hydroxysteroid dehydrogenase type I provide insights into glucocorticoid interconversion and enzyme regulation. J Biol Chem 280(6):4639–4648
8. Jiang SM, Li CH, Zhang WW, Cai YH, Yang YL, Yang S, Jiang WH (2007) Directed evolution and structural analysis of N-carbamoyl-D-amino acid amidohydrolase provide insights into recombinant protein solubility in Escherichia coli. Biochem J 402(3):429–437
9. Lawson AJ, Walker EA, White SA, Dafforn TR, Stewart PM, Ride JP (2009) Mutations of key hydrophobic surface residues of11beta-hydroxysteroid dehydrogenase type I increase solubility and monodispersity in a bacterial expression system. Protein Sci 18(7):1552–63
10. Liu L, Aigner A, Schmid RD (2011) Identification, cloning, heterologous expression, and characterization of a NADPH-dependent 7 beta-hydroxysteroid dehydrogenase from Collinsella aerofaciens. Appl Microbiol Biotechnol 90(1):127–135
11. Lu WY, Du LX, Wang M, Wen HP, Sun B, Guo YW (2006) Effect of two-steps substrate addition on steroids 11 beta-hydroxylation by Curvularia lunata CL-114. Biochem Eng J 32(3):233–238
12. Manosroi J, Abe M, Manosroi A (1999) Biotransformation of steroidal drugs using microorganisms screened from various sites in Chiang Mai, Thailand. Bioresource Technol 69(1):67–73
13. Naim N, Adham NZ, Abd El-Rehim H, Abd El-Hady A. (2003) Prednisolone production using Pseudomonas fluorescens cells immobilized with polymer carrier produced by radiation polymerisation.Process Biochem 38(7):1083–1089
14. Ogg D, Elleby B, Norstrom C, Stefansson K, Abrahmsen L, Oppermann U, Svensson S (2005) The crystal structure of guinea pig 11beta-hydroxysteroid dehydrogenase type I provides a model for enzyme-lipid bilayer interactions. J Biol Chem 280(5):3789–94
15. Pu X, Yang K (2000) Guinea pig 11beta-hydroxysteroid dehydrogenase type I: primary structure and catalytic properties. Steroids 65(3):148–56
16. Sivashanmugam A, Murray V, Cui CX, Zhang YH, Wang JJ, Li QQ (2009) Practical protocols for production of very high yields of recombinant proteins using Escherichia coli. Protein Sci 8(5):936–948
17. Sonomoto K, Hoq MM, Tanaka A, Sukui S (1983) 11-Beta-hydroxylation of cortexolone (Reichstein Compound S) to hydrocortisone by Curvularialunata entrapped in photo-pross-pinked resin gels. Appl Environ Microb 45(2):436–443
18. Sun BQ, Kantzow C, Bresch S, Castiglione K, Weuster-Botz D (2013) Multi-enzymatic one-pot reduction of dehydrocholic acid to 12-keto-ursodeoxycholic acid with whole-cell biocatalysts. Biotechnol Bioeng 110(1):68–77
19. Suzuki K, Sanga K, Chikaoka Y, Itagaki E (1993) Purification and properties of cytochromeP-450 (P-450lun) catalyzing steroid 11-beta-hydroxylation in Curvularia lunata. Biochim Biophys Acta 1203(2):215–223
20. Szczebara FM, Chandelier C, Villeret C, Masurel A, Bourot S, Duport C, Blanchard S, Groisillier A, Testet E, Costaglioli P, Cauet G, Degryse E, Balbuena D, Winter J, Achstetter T, Spagnoli R, Pompon D, Dumas B (2003) Total biosynthesis of hydrocortisone from a simple carbon source in yeast. Nat Biotechnol 21(2):143–149
21. Wang J, Chen CZ, Li BA, Zhang JH, Yu YT (1998) Production of hydrocortisone from cortexolone-21-acetate by immobilized Absidia orchidis in cosolventcontaining media. Enzyme Microb Technol 22(5):368–373
22. Wigley WC, Stidham RD, Smith NM, Hunt JF, Thomas PJ (2001) Protein solubility and folding monitored in vivo by structural complementation of a genetic marker protein. Nat Biotechnol 19(2):131–136
23. Wilmanska D, Milczarek K, Rumijowska A, Bartnicka K, Sedlaczek L (1992) Elimination of by-products in 11beta-hydroxylation of substance S using Curvularia lunata clones regenerated from NTG-treated protoplasts. Appl Microbiol Biotechnol 37(5):626–630
24. Zhang BQ, Zhu HM, Liu XF (2004) Effect of supercritical fluids on C11 beta-hydroxylation activity of Absidia coerulea. Biotechnol Progr 20(6):1885–1887