Author Correction: Complete biosynthesis of cannabinoids and their unnatural analogues in yeast (Nature, (2019), 567, 7746, (123-126), 10.1038/s41586-019-0978-9);Complete biosynthesis of cannabinoids and their unnatural analogues in yeast

Nature

Volumn 567, Issue 7746, 2019, Pages 123-126

  Luo, Xiaozhou ^a   Reiter, Michael A ^a,b   d’Espaux, Leo ^c,k   Wong, Jeff ^c,k   Denby, Charles M ^a,l   Lechner, Anna ^d,e,m   Zhang, Yunfeng ^a,f   Grzybowski, Adrian T ^a   Harth, Simon ^c   Lin, Weiyin ^c   Lee, Hyunsu ^c,d   Yu, Changhua ^c,e   Shin, John ^c,d   Deng, Kai ^g,h   Benites, Veronica T ^c   Wang, George ^c   Baidoo, Edward E K ^c   Chen, Yan ^c   Dev, Ishaan ^c,d   Petzold, Christopher J ^c   Keasling, Jay D ^a,c,d,e,i,j   more..

^a UNIVERSITY OF CALIFORNIA   (United States)

^b ETH ZURICH   (Switzerland)

^c LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

^e University of California   (United States)

^f JIANGNAN UNIVERSITY   (China)

^g UNIVERSITY OF CALIFORNIA   (United States)

^h SANDIA NATIONAL LABORATORIES   (United States)

ⁱ Chalmers University of Technology   (Denmark)

^j Institute for Advanced Study   (China)

^k Demetrix Inc   (United States)

^l Berkeley Brewing Science   (United States)

^m GENOMATICA INC   (United States)

more..

Author keywords

[No Author keywords available]

Indexed keywords

CANNABIDIOLIC ACID; CANNABIDIVARINIC ACID; CANNABIGEROLIC ACID; CANNABINOID DERIVATIVE; GALACTOSE; GERANYL PYROPHOSPHATE; MEVALONIC ACID; PYROPHOSPHATE; TETRAHYDROCANNABINOLIC ACID; UNCLASSIFIED DRUG; ACYL COENZYME A; BENZOIC ACID; CANNABINOID; CANNABIS; DELTA(9)-TETRAHYDROCANNABINOLIC ACID; DRONABINOL; GERANYLPYROPHOSPHATE OLIVETOLATE GERANYLTRANSFERASE; HEXANOYL-COENZYME A; ISOPRENOID PHOSPHATE; OLIVETOLIC ACID; SALICYLIC ACID DERIVATIVE; TRANSFERASE;

AMINO TERMINAL SEQUENCE; BINDING AFFINITY; CANNABIS GENE; CANNABIS SATIVA; CONCENTRATION (PARAMETER); CONTROLLED STUDY; CYCLOADDITION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME ACTIVITY; GENE; GENE OVEREXPRESSION; LETTER; NONHUMAN; PRIORITY JOURNAL; RECEPTOR BINDING; RETENTION TIME; SACCHAROMYCES CEREVISIAE; SIGNAL TRANSDUCTION; YEAST; ANALOGS AND DERIVATIVES; BIOSYNTHESIS; CHEMISTRY; FERMENTATION; GENETICS; METABOLIC ENGINEERING; METABOLISM;

CANNABIS; CANNABIS SATIVA; SACCHAROMYCES CEREVISIAE;

ACYL COENZYME A; ALKYL AND ARYL TRANSFERASES; BENZOATES; BIOSYNTHETIC PATHWAYS; CANNABINOIDS; CANNABIS; DRONABINOL; FERMENTATION; GALACTOSE; METABOLIC ENGINEERING; MEVALONIC ACID; POLYISOPRENYL PHOSPHATES; SACCHAROMYCES CEREVISIAE; SALICYLATES;

EID: 85062584782     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/s41586-020-2109-z     Document Type: Erratum

References (34)

1. Pacher, P., Bátkai, S. & Kunos, G. The endocannabinoid system as an emerging target of pharmacotherapy. Pharmacol. Rev. 58, 389–462 (2006).
2. Whiting, P. F. et al. Cannabinoids for medical use: a systematic review and meta-analysis. J. Am. Med. Assoc. 313, 2456–2473 (2015).
3. Hazekamp, A., Ware, M. A., Muller-Vahl, K. R., Abrams, D. & Grotenhermen, F. The medicinal use of cannabis and cannabinoids—an international cross-sectional survey on administration forms. J. Psychoactive Drugs 45, 199–210 (2013).
4. ElSolhly, M. A. & Gul, W. in Handbook of Cannabis (ed. Pertwee, R. G.) Ch. 1 (Oxford Univ. Press, Oxford, 2014).
5. Dekishima, Y., Lan, E. I., Shen, C. R., Cho, K. M. & Liao, J. C. Extending carbon chain length of 1-butanol pathway for 1-hexanol synthesis from glucose by engineered Escherichia coli. J. Am. Chem. Soc. 133, 11399–11401 (2011).
6. Gagne, S. J. et al. Identification of olivetolic acid cyclase from Cannabis sativa reveals a unique catalytic route to plant polyketides. Proc. Natl Acad. Sci. USA 109, 12811–12816 (2012).
7. Zirpel, B., Stehle, F. & Kayser, O. Production of Δ9-tetrahydrocannabinolic acid from cannabigerolic acid by whole cells of Pichia (Komagataella) pastoris expressing Δ9-tetrahydrocannabinolic acid synthase from Cannabis sativa L. Biotechnol. Lett. 37, 1869–1875 (2015).
8. Taura, F. et al. Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa. FEBS Lett. 581, 2929–2934 (2007).
9. Razdan, R. K. in The Cannabinoid Receptors (ed. Reggio, P. H.) 3–19 (Humana Press, New York, 2009).
10. Taura, F. et al. Characterization of olivetol synthase, a polyketide synthase putatively involved in cannabinoid biosynthetic pathway. FEBS Lett. 583, 2061–2066 (2009).
11. Saerens, S. M. G., Delvaux, F. R., Verstrepen, K. J. & Thevelein, J. M. Production and biological function of volatile esters in Saccharomyces cerevisiae. Microb. Biotechnol. 3, 165–177 (2010).
12. Stout, J. M., Boubakir, Z., Ambrose, S. J., Purves, R. W. & Page, J. E. The hexanoyl-CoA precursor for cannabinoid biosynthesis is formed by an acyl-activating enzyme in Cannabis sativa trichomes. Plant J. 71, 353–365 (2012).
13. Fellermeier, M. & Zenk, M. H. Prenylation of olivetolate by a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol. FEBS Lett. 427, 283–285 (1998).
14. Page, J. E. & Boubakir, Z. Aromatic prenyltransferase from Cannabis. US patent 2012/0144523 A1 (2012).
15. Reider Apel, A. et al. A Cas9-based toolkit to program gene expression in Saccharomyces cerevisiae. Nucleic Acids Res. 45, 496–508 (2017).
16. Ignea, C., Pontini, M., Maffei, M. E., Makris, A. M. & Kampranis, S. C. Engineering monoterpene production in yeast using a synthetic dominant negative geranyl diphosphate synthase. ACS Synth. Biol. 3, 298–306 (2014).
17. Kuzuyama, T., Noel, J. P. & Richard, S. B. Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products. Nature 435, 983–987 (2005).
18. Zirpel, B., Degenhardt, F., Martin, C., Kayser, O. & Stehle, F. Engineering yeasts as platform organisms for cannabinoid biosynthesis. J. Biotechnol. 259, 204–212 (2017).
19. Li, H. et al. A heteromeric membrane-bound prenyltransferase complex from hop catalyzes three sequential aromatic prenylations in the bitter acid pathway. Plant Physiol. 167, 650–659 (2015).
20. van Bakel, H. et al. The draft genome and transcriptome of Cannabis sativa. Genome Biol. 12, R102 (2011).
21. Emanuelsson, O., Brunak, S., von Heijne, G. & Nielsen, H. Locating proteins in the cell using TargetP, SignalP and related tools. Nat. Protocols 2, 953–971 (2007).
22. Emanuelsson, O., Nielsen, H. & von Heijne, G. ChloroP, a neural network-based method for predicting chloroplast transit peptides and their cleavage sites. Protein Sci. 8, 978–984 (1999).
23. Krogh, A., Larsson, B., von Heijne, G. & Sonnhammer, E. L. Predicting transmembrane protein topology with a hidden Markov model: application to complete genomes. J. Mol. Biol. 305, 567–580 (2001).
24. 1-tetrahydrocannabinolic acid biosynthesis. J. Am. Chem. Soc. 117, 9766–9767 (1995).
25. Taura, F., Morimoto, S. & Shoyama, Y. Purification and characterization of cannabidiolic-acid synthase from Cannabis sativa L. Biochemical analysis of a novel enzyme that catalyzes the oxidocyclization of cannabigerolic acid to cannabidiolic acid. J. Biol. Chem. 271, 17411–17416 (1996).
26. 1-tetrahydrocannabinolic acid synthase from Cannabis sativa L. J. Biol. Chem. 279, 39767–39774 (2004).
27. Sirikantaramas, S. et al. Tetrahydrocannabinolic acid synthase, the enzyme controlling marijuana psychoactivity, is secreted into the storage cavity of the glandular trichomes. Plant Cell Physiol. 46, 1578–1582 (2005).
28. de Meijer, E. P. M. & Hammond, K. M. The inheritance of chemical phenotype in Cannabis sativa L. (V): regulation of the propyl-/pentyl cannabinoid ratio, completion of a genetic model. Euphytica 210, 291–307 (2016).
29. Wenig, P. & Odermatt, J. OpenChrom: a cross-platform open source software for the mass spectrometric analysis of chromatographic data. BMC Bioinformatics 11, 405 (2010).
30. McKinney, W. Data structures for statistical computing in Python. In Proc. 9th Python in Science Conference (eds van der Walt, S. & Millman, J.) 51–56 (SciPy, 2010).
31. Edgar, R. C. MUSCLE: multiple sequence alignment with high accuracy and high throughput. Nucleic Acids Res. 32, 1792–1797 (2004).
32. Trifinopoulos, J., Nguyen, L.-T., von Haeseler, A. & Minh, B. Q. W-IQ-TREE: a fast online phylogenetic tool for maximum likelihood analysis. Nucleic Acids Res. 44, W232–W235 (2016).
33. Huerta-Cepas, J., Serra, F. & Bork, P. ETE 3: reconstruction, analysis, and visualization of phylogenomic data. Mol. Biol. Evol. 33, 1635–1638 (2016).
34. Lee, T. S. et al. BglBrick vectors and datasheets: a synthetic biology platform for gene expression. J. Biol. Eng. 5, 12 (2011).