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Volumn 57, Issue , 2020, Pages 31-42

Identification of Absidia orchidis steroid 11β-hydroxylation system and its application in engineering Saccharomyces cerevisiae for one-step biotransformation to produce hydrocortisone

Author keywords

11 hydroxylation; Absidia orchidis; Hydrocortisone; Saccharomyces cerevisiae; Steroid; Transporter

Indexed keywords

BIOCONVERSION; CAPILLARY FLOW; GENES; HYDROXYLATION; PRODUCTIVITY; STEREOCHEMISTRY; YEAST;

EID: 85074154351     PISSN: 10967176     EISSN: 10967184     Source Type: Journal    
DOI: 10.1016/j.ymben.2019.10.006     Document Type: Article
Times cited : (54)

References (50)
  • 1
    • 84865827131 scopus 로고    scopus 로고
    • Biological transformations of steroidal compounds: a review
    • Bhatti, H. N., Khera, R. A., 2012. Biological transformations of steroidal compounds: a review. Steroids. 77, 1267-1290.
    • (2012) Steroids , vol.77 , pp. 1267-1290
    • Bhatti, H.N.1    Khera, R.A.2
  • 2
    • 0036806162 scopus 로고    scopus 로고
    • The human steroid hydroxylases CYP1B1 and CYP11B2
    • Bureik, M., Lisurek, M., Bernhardt, R., 2002. The human steroid hydroxylases CYP1B1 and CYP11B2. Biol. Chem. 383, 1537-1551.
    • (2002) Biol. Chem. , vol.383 , pp. 1537-1551
    • Bureik, M.1    Lisurek, M.2    Bernhardt, R.3
  • 3
    • 34248199836 scopus 로고    scopus 로고
    • The 11 beta-hydroxylation of 16,17 alpha-epoxyprogesterone and the purification of the 11 beta-hydroxylase from Absidia coerulea IBL02
    • Chen, K., Tong, W. Y., Wei, D. Z., Jiang, W., 2007. The 11 beta-hydroxylation of 16,17 alpha-epoxyprogesterone and the purification of the 11 beta-hydroxylase from Absidia coerulea IBL02. Enzyme Microb. Tech. 41, 71-79.
    • (2007) Enzym. Microb. Technol. , vol.41 , pp. 71-79
    • Chen, K.1    Tong, W.Y.2    Wei, D.Z.3    Jiang, W.4
  • 5
    • 85074156955 scopus 로고    scopus 로고
    • Process for Preparing Genetically Transformed Yeasts Capable of Producing a Molecule of Interest at a High Titre. Patent US 9994888B2.
    • Corinne, B. M., Isabelle, B., Dumas, B., 2018. Process for Preparing Genetically Transformed Yeasts Capable of Producing a Molecule of Interest at a High Titre. Patent US 9994888B2.
    • (2018)
    • Corinne, B.M.1    Isabelle, B.2    Dumas, B.3
  • 6
    • 85055650603 scopus 로고    scopus 로고
    • Identification of a novel cytochrome P450 enzyme that catalyzes the C-2alpha hydroxylation of pentacyclic triterpenoids and its application in yeast cell factories
    • Dai, Z., Liu, Y., Sun, Z., Wang, D., Qu, G., Ma, X., Fan, F., Zhang, L., Li, S., Zhang, X., 2019. Identification of a novel cytochrome P450 enzyme that catalyzes the C-2alpha hydroxylation of pentacyclic triterpenoids and its application in yeast cell factories. Metab. Eng. 51, 70-78.
    • (2019) Metab. Eng. , vol.51 , pp. 70-78
    • Dai, Z.1    Liu, Y.2    Sun, Z.3    Wang, D.4    Qu, G.5    Ma, X.6    Fan, F.7    Zhang, L.8    Li, S.9    Zhang, X.10
  • 7
    • 84886486790 scopus 로고    scopus 로고
    • Metabolic engineering of Saccharomyces cerevisiae for production of ginsenosides
    • Dai, Z., Liu, Y., Zhang, X., Shi, M., Wang, B., Wang, D., Huang, L., Zhang, X., 2013. Metabolic engineering of Saccharomyces cerevisiae for production of ginsenosides. Metab. Eng. 20, 146-156.
    • (2013) Metab. Eng. , vol.20 , pp. 146-156
    • Dai, Z.1    Liu, Y.2    Zhang, X.3    Shi, M.4    Wang, B.5    Wang, D.6    Huang, L.7    Zhang, X.8
  • 9
    • 84866309060 scopus 로고    scopus 로고
    • Microbial steroid transformations: current state and prospects
    • Donova, M. V., Egorova, O. V., 2012. Microbial steroid transformations: current state and prospects. Appl. Microbiol. Biotechnol. 94, 1423-1447.
    • (2012) Appl. Microbiol. Biotechnol. , vol.94 , pp. 1423-1447
    • Donova, M.V.1    Egorova, O.V.2
  • 10
    • 0029888511 scopus 로고    scopus 로고
    • 11 beta-hydroxylase activity in recombinant yeast mitochondria - in vivo conversion of 11-deoxycortisol to hydrocortisone
    • Dumas, B., Cauet, G., Lacour, T., Degryse, E., Laruelle, L., Ledoux, C., Spagnoli, R., Achstetter, T., 1996. 11 beta-hydroxylase activity in recombinant yeast mitochondria - In vivo conversion of 11-deoxycortisol to hydrocortisone. Eur. J. Biochem. 238, 495-504.
    • (1996) Eur. J. Biochem. , vol.238 , pp. 495-504
    • Dumas, B.1    Cauet, G.2    Lacour, T.3    Degryse, E.4    Laruelle, L.5    Ledoux, C.6    Spagnoli, R.7    Achstetter, T.8
  • 11
    • 33749036014 scopus 로고    scopus 로고
    • Hydrocortisone made in yeast: metabolic engineering turns a unicellular microorganism into a drug-synthesizing factory
    • Dumas, B., Brocard-Masson, C., Assemat-Lebrun, K., Achstetter, T., 2006. Hydrocortisone made in yeast: metabolic engineering turns a unicellular microorganism into a drug-synthesizing factory. Biotechnol. J. 1, 299-307.
    • (2006) Biotechnol. J. , vol.1 , pp. 299-307
    • Dumas, B.1    Brocard-Masson, C.2    Assemat-Lebrun, K.3    Achstetter, T.4
  • 13
    • 37349007629 scopus 로고    scopus 로고
    • Coexpression of redox partners increases the hydrocortisone (cortisol) production efficiency in CYP11B1 expressing fission yeast Schizosaccharomyces pombe
    • Hakki, T., Zearo, S., Dragan, C. A., 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, 351-359.
    • (2008) J. Biotechnol. , vol.133 , pp. 351-359
    • Hakki, T.1    Zearo, S.2    Dragan, C.A.3    Bureik, M.4    Bernhardt, R.5
  • 14
    • 51849171075 scopus 로고
    • Microbiological transformation of steroids. XV. Transformation of steroid s (Reichstein) by Absidia orchidis 310
    • Hanc, O., Capek, A., Kakac, B., 1961. Microbiological transformation of steroids. XV. Transformation of steroid s (Reichstein) by Absidia orchidis 310. Folia. Microbiol (Praha). 6, 392-397.
    • (1961) Folia Microbiol. , vol.6 , pp. 392-397
    • Hanc, O.1    Capek, A.2    Kakac, B.3
  • 15
    • 0029643786 scopus 로고
    • Structure and function of cytochromes P450: a comparative analysis of three crystal structures
    • Hasemann, C. A., Kurumbail, R. G., Boddupalli, S. S., Peterson, J. A., Deisenhofer, J., 1995. Structure and function of cytochromes P450: a comparative analysis of three crystal structures. Structure. 3, 41-62.
    • (1995) Structure , vol.3 , pp. 41-62
    • Hasemann, C.A.1    Kurumbail, R.G.2    Boddupalli, S.S.3    Peterson, J.A.4    Deisenhofer, J.5
  • 16
    • 84883590772 scopus 로고    scopus 로고
    • GalaxyRefine: protein structure refinement driven by side-chain repacking
    • Heo, L., Park, H., Seok, C., 2013. GalaxyRefine: Protein structure refinement driven by side-chain repacking. Nucleic. Acids Res. 41, W384-388.
    • (2013) Nucleic Acids Res. , vol.41 , pp. W384-W388
    • Heo, L.1    Park, H.2    Seok, C.3
  • 17
    • 85024493874 scopus 로고    scopus 로고
    • Chemical pathways of corticosteroids, industrial synthesis from sapogenins
    • Herraiz, I., 2017. Chemical Pathways of Corticosteroids, Industrial Synthesis from Sapogenins. Methods Mol. Biol. 1645, 15-27.
    • (2017) Methods Mol. Biol. , vol.1645 , pp. 15-27
    • Herraiz, I.1
  • 18
    • 84925334556 scopus 로고    scopus 로고
    • Substrate tunnels in enzymes: structure-function relationships and computational methodology
    • Kingsley, L. J., Lill, M. A., 2015. Substrate tunnels in enzymes: structure-function relationships and computational methodology. Proteins. 83, 599-611.
    • (2015) Proteins , vol.83 , pp. 599-611
    • Kingsley, L.J.1    Lill, M.A.2
  • 19
    • 85067583630 scopus 로고    scopus 로고
    • High-yield C11-oxidation of hydrocortisone by establishment of an efficient whole-cell system in Bacillus megaterium
    • Konig, L., Hartz, P., Bernhardt, R., Hannemann, F., 2019. High-yield C11-oxidation of hydrocortisone by establishment of an efficient whole-cell system in Bacillus megaterium. Metab. Eng. 55, 59-67.
    • (2019) Metab. Eng. , vol.55 , pp. 59-67
    • Konig, L.1    Hartz, P.2    Bernhardt, R.3    Hannemann, F.4
  • 21
    • 39749101683 scopus 로고    scopus 로고
    • High diversity and complex evolution of fungal cytochrome P450 reductase: cytochrome P450 systems
    • Lah, L., Krasevec, N., Trontelj, P., Komel, R., 2008. High diversity and complex evolution of fungal cytochrome P450 reductase: cytochrome P450 systems. Fungal Genet. Biol. 45, 446-458.
    • (2008) Fungal Genet. Biol. , vol.45 , pp. 446-458
    • Lah, L.1    Krasevec, N.2    Trontelj, P.3    Komel, R.4
  • 22
    • 0000243829 scopus 로고
    • Procheck - a program to check the stereochemical quality of protein structures
    • Laskowski, R. A., Macarthur, M. W., Moss, D. S., Thornton, J. M., 1993. Procheck - a Program to Check the Stereochemical Quality of Protein Structures. J. Appl. Crystallogr. 26, 283-291.
    • (1993) J. Appl. Crystallogr. , vol.26 , pp. 283-291
    • Laskowski, R.A.1    Macarthur, M.W.2    Moss, D.S.3    Thornton, J.M.4
  • 23
    • 79961123152 scopus 로고    scopus 로고
    • RSEM: accurate transcript quantification from RNA-Seq data with or without a reference genome
    • Li, B., Dewey, C. N., 2011. RSEM: accurate transcript quantification from RNA-Seq data with or without a reference genome. BMC Bioinformatics. 12: 323.
    • (2011) BMC Bioinf. , vol.12 , pp. 323
    • Li, B.1    Dewey, C.N.2
  • 24
    • 84941962714 scopus 로고    scopus 로고
    • De novo production of resveratrol from glucose or ethanol by engineered Saccharomyces cerevisiae
    • Li, M., Kildegaard, K. R., Chen, Y., Rodriguez, A., Borodina, I., Nielsen, J., 2015. De novo production of resveratrol from glucose or ethanol by engineered Saccharomyces cerevisiae. Metab. Eng. 32, 1-11.
    • (2015) Metab. Eng. , vol.32 , pp. 1-11
    • Li, M.1    Kildegaard, K.R.2    Chen, Y.3    Rodriguez, A.4    Borodina, I.5    Nielsen, J.6
  • 25
    • 33744498614 scopus 로고    scopus 로고
    • Occupational endotoxin-exposure and possible health effects on humans
    • Liebers, V., Bruning, T., Raulf-Heimsoth, M., 2006. Occupational endotoxin-exposure and possible health effects on humans. Am. J. Ind. Med. 49, 474-491.
    • (2006) Am. J. Ind. Med. , vol.49 , pp. 474-491
    • Liebers, V.1    Bruning, T.2    Raulf-Heimsoth, M.3
  • 26
    • 33750980728 scopus 로고    scopus 로고
    • Effect of two-steps substrate addition on steroids 11β-hydroxylation by Curvularia lunata CL-114
    • Lu, W., Du, L., Wang, M., Wen, J., Sun, B., Guo, Y., 2006. Effect of two-steps substrate addition on steroids 11β-hydroxylation by Curvularia lunata CL-114. Biochem. Eng. J. 32, 233-238.
    • (2006) Biochem. Eng. J. , vol.32 , pp. 233-238
    • Lu, W.1    Du, L.2    Wang, M.3    Wen, J.4    Sun, B.5    Guo, Y.6
  • 27
    • 85057886446 scopus 로고    scopus 로고
    • Lipid engineering combined with systematic metabolic engineering of Saccharomyces cerevisiae for high-yield production of lycopene
    • Ma, T., Shi, B., Ye, Z., Li, X., Liu, M., Chen, Y., Xia, J., Nielsen, J., Deng, Z., Liu, T., 2018. Lipid engineering combined with systematic metabolic engineering of Saccharomyces cerevisiae for high-yield production of lycopene. Metab. Eng. 52, 134-142.
    • (2018) Metab. Eng. , vol.52 , pp. 134-142
    • Ma, T.1    Shi, B.2    Ye, Z.3    Li, X.4    Liu, M.5    Chen, Y.6    Xia, J.7    Nielsen, J.8    Deng, Z.9    Liu, T.10
  • 28
    • 0017588168 scopus 로고
    • A study of the preferred environment of amino acid residues in globular proteins
    • Manavalan, P., Ponnuswamy, P. K., 1977. A study of the preferred environment of amino acid residues in globular proteins. Arch. Biochem. Biophys. 184, 476-487.
    • (1977) Arch. Biochem. Biophys. , vol.184 , pp. 476-487
    • Manavalan, P.1    Ponnuswamy, P.K.2
  • 30
    • 77349091080 scopus 로고    scopus 로고
    • Hydrocarbon hydroxylation by cytochrome P450 enzymes
    • Ortiz de Montellano, P. R., 2010. Hydrocarbon hydroxylation by cytochrome P450 enzymes. Chem. Rev. 110, 932-948.
    • (2010) Chem. Rev. , vol.110 , pp. 932-948
    • Ortiz de Montellano, P.R.1
  • 31
    • 85074134301 scopus 로고    scopus 로고
    • Genetic Transformation of Zygomycetes Fungi
    • Springer Netherlands
    • Papp, T., Csernetics, A., Nyilasi, I., ABrOk, M., VAgvOlgyi, C., 2015. Genetic Transformation of Zygomycetes Fungi. Springer Netherlands. 75-94.
    • (2015) , pp. 75-94
    • Papp, T.1    Csernetics, Á.2    Nyilasi, I.3    ÁBrÓk, M.4    VÁgvÓlgyi, C.5
  • 35
    • 79551667941 scopus 로고    scopus 로고
    • Circular polymerase extension cloning for high-throughput cloning of complex and combinatorial DNA libraries
    • Quan, J., Tian, J., 2011. Circular polymerase extension cloning for high-throughput cloning of complex and combinatorial DNA libraries. Nat. Protoc. 6, 242-251.
    • (2011) Nat. Protoc. , vol.6 , pp. 242-251
    • Quan, J.1    Tian, J.2
  • 37
    • 77954065271 scopus 로고    scopus 로고
    • I-TASSER: a unified platform for automated protein structure and function prediction
    • Roy, A., Kucukural, A., Zhang, Y., 2010. I-TASSER: a unified platform for automated protein structure and function prediction. Nat. Protoc. 5, 725-738.
    • (2010) Nat. Protoc. , vol.5 , pp. 725-738
    • Roy, A.1    Kucukural, A.2    Zhang, Y.3
  • 38
    • 84924238487 scopus 로고    scopus 로고
    • A recombinant CYP11B1 dependent Escherichia coli biocatalyst for selective cortisol production and optimization towards a preparative scale
    • Schiffer, L., Anderko, S., Hobler, A., Hannemann, F., Kagawa, N., Bernhardt, R., 2015. A recombinant CYP11B1 dependent Escherichia coli biocatalyst for selective cortisol production and optimization towards a preparative scale. Microb. Cell Fact. 14, 25.
    • (2015) Microb. Cell Factories , vol.14 , pp. 25
    • Schiffer, L.1    Anderko, S.2    Hobler, A.3    Hannemann, F.4    Kagawa, N.5    Bernhardt, R.6
  • 39
    • 0020677888 scopus 로고
    • 11beta-Hydroxylation of cortexolone (Reichstein compound S) to hydrocortisone by Curvularia lunata entrapped in photo-cross-linked resin gels
    • Sonomoto, K., Hoq, M. M., Tanaka, A., Fukui, S., 1983. 11beta-Hydroxylation of Cortexolone (Reichstein Compound S) to Hydrocortisone by Curvularia lunata Entrapped in Photo-Cross-Linked Resin Gels. Appl. Environ. Microbiol. 45, 436-443.
    • (1983) Appl. Environ. Microbiol. , vol.45 , pp. 436-443
    • Sonomoto, K.1    Hoq, M.M.2    Tanaka, A.3    Fukui, S.4
  • 40
    • 0027755164 scopus 로고
    • (Lun)) catalyzing steroid 11-beta-hydroxylation in Curvularia lunata
    • Suzuki, K., Sanga, K., Chikaoka, Y., Itagaki, E., 1993. Purification and Properties of Cytochrome-P-450 (P-450(Lun)) Catalyzing Steroid 11-Beta-Hydroxylation in Curvularia lunata. Biochim. Biophys. Acta. 1203, 215-223.
    • (1993) Biochim. Biophys. Acta , vol.1203 , pp. 215-223
    • Suzuki, K.1    Sanga, K.2    Chikaoka, Y.3    Itagaki, E.4
  • 44
    • 3042587451 scopus 로고    scopus 로고
    • A survey of active site access channels in cytochromes P450
    • Wade, R. C., Winn, P. J., Schlichting, I., Sudarko, 2004. A survey of active site access channels in cytochromes P450. J. Inorg. Biochem. 98, 1175-1182.
    • (2004) J. Inorg. Biochem. , vol.98 , pp. 1175-1182
    • Wade, R.C.1    Winn, P.J.2    Schlichting, I.3    Sudarko4
  • 46
    • 85044089612 scopus 로고    scopus 로고
    • De novo synthesis of the sedative valerenic acid in Saccharomyces cerevisiae
    • Wong, J., d'Espaux, L., Dev, I., van der Horst, C., Keasling, J., 2018. De novo synthesis of the sedative valerenic acid in Saccharomyces cerevisiae. Metab. Eng. 47, 94-101.
    • (2018) Metab. Eng. , vol.47 , pp. 94-101
    • Wong, J.1    d'Espaux, L.2    Dev, I.3    van der Horst, C.4    Keasling, J.5
  • 47
    • 34547566446 scopus 로고    scopus 로고
    • ProSA-web: interactive web service for the recognition of errors in three-dimensional structures of proteins
    • Wiederstein, M., Sippl, M. J., 2007. ProSA-web: interactive web service for the recognition of errors in three-dimensional structures of proteins. Nucleic. Acids Res. 35, W407-410.
    • (2007) Nucleic Acids Res. , vol.35 , pp. W407-W410
    • Wiederstein, M.1    Sippl, M.J.2
  • 48
    • 84903549014 scopus 로고    scopus 로고
    • sgRNAcas9: a software package for designing CRISPR sgRNA and evaluating potential off-target cleavage sites
    • Xie, S., Shen, B., Zhang, C., Huang, X., Zhang, Y., 2014. sgRNAcas9: a software package for designing CRISPR sgRNA and evaluating potential off-target cleavage sites. PLoS One. 9, e100448.
    • (2014) PLoS One , vol.9
    • Xie, S.1    Shen, B.2    Zhang, C.3    Huang, X.4    Zhang, Y.5
  • 49
    • 85020734826 scopus 로고    scopus 로고
    • Cell foundry with high product specificity and catalytic activity for 21-deoxycortisol biotransformation
    • Xiong, S., Wang, Y., Yao, M., Liu, H., Zhou, X., Xiao, W., Yuan, Y., 2017. Cell foundry with high product specificity and catalytic activity for 21-deoxycortisol biotransformation. Microb. Cell Fact. 16, 105.
    • (2017) Microb. Cell Factories , vol.16 , pp. 105
    • Xiong, S.1    Wang, Y.2    Yao, M.3    Liu, H.4    Zhou, X.5    Xiao, W.6    Yuan, Y.7
  • 50
    • 10044298412 scopus 로고    scopus 로고
    • Effect of supercritical fluids on C11beta-hydroxylation activity of Absidia coerulea
    • Zhang, B., Zhu, H., Liu, X., 2004. Effect of supercritical fluids on C11beta-hydroxylation activity of Absidia coerulea. Biotechnol. Prog. 20, 1885-1887.
    • (2004) Biotechnol. Prog. , vol.20 , pp. 1885-1887
    • Zhang, B.1    Zhu, H.2    Liu, X.3


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