Computational redesign of taxane-10β-hydroxylase for de novo biosynthesis of a key paclitaxel intermediate

Abdallah II, Pramastya H, van Merkerk R, Sukrasno QWJ (2019) Metabolic engineering of Bacillus subtilis toward taxadiene biosynthesis as the first committed step for taxol production. Front Microbiol 10:218. https://doi.org/10.3389/fmicb.2019.00218

Article  PubMed  PubMed Central  Google Scholar 

Acevedo-Rocha CG, Li A, D’Amore L, Hoebenreich S, Sanchis J, Lubrano P, Ferla MP, Garcia-Borràs M, Osuna S, Reetz MT (2021) Pervasive cooperative mutational effects on multiple catalytic enzyme traits emerge via long-range conformational dynamics. Nat Commun 12(1):1621. https://doi.org/10.1038/s41467-021-21833-w

Article  CAS  PubMed  PubMed Central  Google Scholar 

Ajikumar PK, Xiao WH, Tyo KEJ, Wang Y, Simeon F, Leonard E, Mucha O, Phon TH, Pfeifer B, Stephanopoulos G (2010) Isoprenoid pathway optimization for taxol precursor overproduction in Escherichia coli. Science 330(6000):70–74. https://doi.org/10.1126/science.1191652

Article  CAS  PubMed  PubMed Central  Google Scholar 

Alonso-Gutierrez J, Chan R, Batth TS, Adams PD, Keasling JD, Petzold CJ, Lee TS (2013) Metabolic engineering of Escherichia coli for limonene and perillyl alcohol production. Metab Eng 19:33–41. https://doi.org/10.1016/j.ymben.2013.05.004

Article  CAS  PubMed  Google Scholar 

Barnes HJ, Arlotto MP, Waterman MR (1991) Expression and enzymatic activity of recombinant cytochrome P450 17 alpha-hydroxylase in Escherichia coli. Proc Natl Acad Sci USA 88(13):5597–5601. https://doi.org/10.1073/pnas.88.13.5597

Article  CAS  PubMed  PubMed Central  Google Scholar 

Bernhofer M, Dallago C, Karl T, Satagopam V, Heinzinger M, Littmann M, Olenyi T, Qiu J, Schütze K, Yachdav G, Ashkenazy H, Ben-Tal N, Bromberg Y, Goldberg T, Kajan L, O’Donoghue S, Sander C, Schafferhans A, Schlessinger A, Vriend G, Mirdita M, Gawron P, Gu W, Jarosz Y, Trefois C, Steinegger M, Schneider R, Rost B (2021) PredictProtein - Predicting protein structure and function for 29 years. Nucleic Acids Res 49(W1):W535–W540. https://doi.org/10.1093/nar/gkab354

Article  CAS  PubMed  PubMed Central  Google Scholar 

Biggs BW, Lim CG, Sagliani K, Shankar S, Stephanopoulos G, De Mey M, Ajikumar PK (2016a) Overcoming heterologous protein interdependency to optimize P450-mediated taxol precursor synthesis in Escherichia coli. Proc Natl Acad Sci USA 113(12):3209–3214. https://doi.org/10.1073/pnas.1515826113

Article  CAS  PubMed  PubMed Central  Google Scholar 

Biggs BW, Rouck JE, Kambalyal A, Arnold W, Lim CG, De Mey M, O’Neil-Johnson M, Starks CM, Das A, Ajikumar PK (2016b) Orthogonal assays clarify the oxidative biochemistry of Taxol P450 CYP725A4. ACS Chem Biol 11(5):1445–1451. https://doi.org/10.1021/acschembio.5b00968

Article  CAS  PubMed  Google Scholar 

Campeotto I, Goldenzweig A, Davey J, Barfod L, Marshall JM, Silk SE, Wright KE, Draper SJ, Higgins MK, Fleishman SJ (2017) One-step design of a stable variant of the malaria invasion protein RH5 for use as a vaccine immunogen. Proc Natl Acad Sci USA 114(5):998–1002. https://doi.org/10.1073/pnas.1616903114

Article  CAS  PubMed  PubMed Central  Google Scholar 

Chau M, Croteau R (2004) Molecular cloning and characterization of a cytochrome P450 taxoid 2alpha-hydroxylase involved in Taxol biosynthesis. Arch Biochem Biophys 427(1):48–57. https://doi.org/10.1016/j.abb.2004.04.016

Article  CAS  PubMed  Google Scholar 

Chau M, Jennewein S, Walker K, Croteau R (2004) Taxol biosynthesis: molecular cloning and characterization of a cytochrome P450 taxoid 7 beta-hydroxylase. Chem Biol 11(5):663–672. https://doi.org/10.1016/j.chembiol.2004.02.025

Article  CAS  PubMed  Google Scholar 

Cheesman MJ, Traylor MJ, Hilton ME, Richards KE, Taylor MC, Daborn PJ, Russell RJ, Gillam EM, Oakeshott JG (2013) Soluble and membrane-bound Drosophila melanogaster CYP6G1 expressed in Escherichia coli: purification, activity, and binding properties toward multiple pesticides. Insect Biochem Mol Biol 43(5):455–465. https://doi.org/10.1016/j.ibmb.2013.02.003

Article  CAS  PubMed  Google Scholar 

Chen S, Wu JL, Liang Y, Tang YG, Song HX, Wu LL, Xing YF, Yan N, Li YT, Wang ZY, Xiao SJ, Lu X, Chen SJ, Lu M (2021) Arsenic trioxide rescues structural p53 mutations through a cryptic allosteric site. Cancer Cell 39(2):225–239. https://doi.org/10.1016/j.ccell.2020.11.013

Article  CAS  PubMed  Google Scholar 

DeJong JHM, Liu Y, Bollon AP, Long RM, Jennewein S, Williams D, Croteau RB (2006) Genetic engineering of taxol biosynthetic genes in Saccharomyces cerevisiae. Biotechnol Bioeng 93(2):212–224. https://doi.org/10.1002/bit.20694

Article  CAS  PubMed  Google Scholar 

Edgar S, Zhou K, Qiao K, King JR, Simpson JH, Stephanopoulos G (2016) Mechanistic insights into taxadiene epoxidation by taxadiene-5α-hydroxylase. ACS Chem Biol 11(2):460–469. https://doi.org/10.1021/acschembio.5b00767

Article  CAS  PubMed  Google Scholar 

Engels B, Dahm P, Jennewein S (2008) Metabolic engineering of taxadiene biosynthesis in yeast as a first step towards Taxol (Paclitaxel) production. Metab Eng 10(3–4):201–206. https://doi.org/10.1016/j.ymben.2008.03.001

Article  CAS  PubMed  Google Scholar 

Gialama D, Kostelidou K, Michou M, Delivoria DC, Kolisis FN, Skretas G (2017) Development of Escherichia coli strains that withstand membrane protein-induced toxicity and achieve high-level recombinant membrane protein production. ACS Synth Biol 6(2):284–300. https://doi.org/10.1021/acssynbio.6b00174

Article  CAS  PubMed  Google Scholar 

Goldenzweig A, Goldsmith M, Hill SE, Gertman O, Laurino P, Ashani Y, Dym O, Unger T, Albeck S, Prilusky J, Lieberman RL, Aharoni A, Silman I, Sussman JL, Tawfik DS, Fleishman SJ (2016) Automated structure- and sequence-based design of proteins for high bacterial expression and stability. Mol Cell 63(2):337–346. https://doi.org/10.1016/j.molcel.2016.06.012

Article  CAS  PubMed  PubMed Central  Google Scholar 

Gubellini F, Verdon G, Karpowich NK, Luff JD, Boël G, Gauthier N, Handelman SK, Ades SE, Hunt JF (2011) Physiological response to membrane protein overexpression in E. coli. Mol Cell Proteomics 10(10):M111.007930. https://doi.org/10.1074/mcp.M111.007930

Article  CAS  PubMed  PubMed Central  Google Scholar 

Hausjell J, Halbwirth H, Spadiut O (2018) Recombinant production of eukaryotic cytochrome P450s in microbial cell factories. Biosci Rep 38(2):BSR20171290. https://doi.org/10.1042/BSR20171290

Article  CAS  PubMed  PubMed Central  Google Scholar 

Hu B, Zhao X, Wang E, Zhou J, Li J, Chen J, Du G (2023) Efficient heterologous expression of cytochrome P450 enzymes in microorganisms for the biosynthesis of natural products. Crit Rev Biotechnol 43(2):227–241. https://doi.org/10.1080/07388551.2022.2029344

Article  CAS  PubMed  Google Scholar 

Huang Q, Roessner CA, Croteaul R, Scott AI, Huang QL, Roessner C (2001) Engineering Escherichia coli for the synthesis of taxadiene, a key intermediate in the biosynthesis of taxol. Bioorgan Med Chem 9(9):2237–2242. https://doi.org/10.1016/s0968-0896(01)00072-4

Article  CAS  Google Scholar 

Jennewein S, Rithner CD, Williams RM, Croteau RB (2001) Taxol biosynthesis: taxane 13 alpha-hydroxylase is a cytochrome P450-dependent monooxygenase. Proc Natl Acad Sci USA 98(24):13595–13600. https://doi.org/10.1073/pnas.251539398

Article  CAS  PubMed  PubMed Central  Google Scholar 

Jennewein S, Long RM, Williams RM, Croteau R (2004) Cytochrome p450 taxadiene 5alpha-hydroxylase, a mechanistically unusual monooxygenase catalyzing the first oxygenation step of taxol biosynthesis. Chem Biol 11(3):379–387. https://doi.org/10.1016/j.chembiol.2004.02.022

Article  CAS  PubMed  Google Scholar 

Jennewein S, Park H, DeJong JM, Long RM, Bollon AP, Croteau RB (2005) Coexpression in yeast of Taxus cytochrome P450 reductase with cytochrome P450 oxygenases involved in Taxol biosynthesis. Biotechnol Bioeng 89(5):588–598. https://doi.org/10.1002/bit.20390

Article  CAS  PubMed  Google Scholar 

Jumper J, Evans R, Pritzel A, Green T, Figurnov M, Ronneberger O, Tunyasuvunakool K, Bates R, Žídek A, Potapenko A, Bridgland A, Meyer C, Kohl SAA, Ballard AJ, Cowie A, Romera-Paredes B, Nikolov S, Jain R, Adler J, Back T, Petersen S, Reiman D, Clancy E, Zielinski M, Steinegger M, Pacholska M, Berghammer T, Bodenstein S, Silver D, Vinyals O, Senior AW, Kavukcuoglu K, Kohli P, Hassabis D (2021) Highly accurate protein structure prediction with AlphaFold. Nature 596(7873):583–589. https://doi.org/10.1038/s41586-021-03819-2

Article  CAS  PubMed  PubMed Central  Google Scholar 

Kriegel M, Wiederanders HJ, Alkhashrom S, Eichler J, Muller YA (2021) A PROSS-designed extensively mutated estrogen receptor α variant displays enhanced thermal stability while retaining native allosteric regulation and structure. Sci Rep 11(1):10509. https://doi.org/10.1038/s41598-021-89785-1

Article  CAS  PubMed  PubMed Central  Google Scholar 

Lv X, Gu J, Wang F, Xie W, Liu M, Ye L, Yu H (2016) Combinatorial pathway optimization in Escherichia coli by directed co-evolution of rate-limiting enzymes and modular pathway engineering. Biotechnol Bioeng 113(12):2661–2669. https://doi.org/10.1002/bit.26034

Article  CAS  PubMed  Google Scholar 

Malladi SK, Schreiber D, Pramanick I, Sridevi MA, Goldenzweig A, Dutta S, Fleishman SJ, Varadarajan R (2020) One-step sequence and structure-guided optimization of HIV-1 envelope gp140. Curr Res Struct Biol 2:45–55. https://doi.org/10.1016/j.crstbi.2020.04.001

Article  PubMed  PubMed Central 

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