Beyond the cyclopropyl ring formation: fungal Aj_EasH catalyzes asymmetric hydroxylation of ergot alkaloids.


Journal

Applied microbiology and biotechnology
ISSN: 1432-0614
Titre abrégé: Appl Microbiol Biotechnol
Pays: Germany
ID NLM: 8406612

Informations de publication

Date de publication:
Apr 2022
Historique:
received: 02 11 2021
accepted: 19 03 2022
revised: 12 03 2022
pubmed: 8 4 2022
medline: 6 5 2022
entrez: 7 4 2022
Statut: ppublish

Résumé

Ergot alkaloids (EAs) are among the most important bioactive natural products. Fe

Identifiants

pubmed: 35389067
doi: 10.1007/s00253-022-11892-4
pii: 10.1007/s00253-022-11892-4
doi:

Substances chimiques

Ergot Alkaloids 0
Ferrous Compounds 0
Alpha-Ketoglutarate-Dependent Dioxygenase FTO EC 1.14.11.33

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

2981-2991

Subventions

Organisme : National Research and Development Program of China
ID : 2019YFA0905100
Organisme : National Research and Development Program of China
ID : 2018YFA0901600
Organisme : the Senior User Project of RV KEXUE, Center for Ocean Mega-Science, CAS
ID : KEXUE2019GZ05
Organisme : National Natural Science Foundation of China
ID : 31872614
Organisme : National Natural Science Foundation of China
ID : 32001036
Organisme : Youth Innovation Promotion Association of the Chinese Academy of Sciences
ID : 2019090
Organisme : Innovative Cross Team project of CAS
ID : JCTD-2019-06

Informations de copyright

© 2022. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.

Références

Bilovol Y, Panaccione DG (2016) Functional analysis of the gene controlling hydroxylation of festuclavine in the ergot alkaloid pathway of Neosartorya fumigata. Curr Genet 62(4):853–860. https://doi.org/10.1007/s00294-016-0591-5
doi: 10.1007/s00294-016-0591-5 pubmed: 26972831 pmcid: 5023448
Brauer A, Beck P, Hintermann L, Groll M (2016) Structure of the dioxygenase AsqJ: mechanistic insights into a one-pot multistep quinolone antibiotic biosynthesis. Angew Chem Int Ed Engl 55(1):422–426. https://doi.org/10.1002/anie.201507835
doi: 10.1002/anie.201507835 pubmed: 26553478
Cernak T, Dykstra KD, Tyagarajan S, Vachal P, Krska SW (2016) The medicinal chemist’s toolbox for late stage functionalization of drug-like molecules. Chem Soc Rev 45(3):546–576. https://doi.org/10.1039/c5cs00628g
doi: 10.1039/c5cs00628g pubmed: 26507237
Chen J-J, Han M-Y, Gong T, Yang J-L, Zhu P (2017) Recent progress in ergot alkaloid research. RSC Adv 7(44):27384–27396. https://doi.org/10.1039/c7ra03152a
doi: 10.1039/c7ra03152a
Cheng JZ, Coyle CM, Panaccione DG, O’Connor SE (2010) Controlling a structural branch point in ergot alkaloid biosynthesis. J Am Chem Soc 132(37):12835–12837. https://doi.org/10.1021/ja105785p
doi: 10.1021/ja105785p pubmed: 20735127 pmcid: 2939906
Chirivi C, Fontana G, Monti D, Ottolina G, Riva S, Danieli B (2012) The quest for new mild and selective modifications of natural structures: laccase-catalysed oxidation of ergot alkaloids leads to unexpected stereoselective C-4 hydroxylation. Chem (Weinheim Bergstrasse, Germany) 18(33):10355–10361. https://doi.org/10.1002/chem.201201076
doi: 10.1002/chem.201201076
Dickhaut J, Molt A, Röckl J (2021) Chapter 17 Cycloclavine: A natural product with insecticidal potential. In: Maienfisch P, Mangelinckx S (eds) Recent Highlights in the Discovery and Optimization of Crop Protection Products. 289–295. https://doi.org/10.1016/b978-0-12-821035-2.00016-4
Einsiedler M, Jamieson CS, Maskeri MA, Houk KN, Gulder TAM (2021) Fungal dioxygenase AsqJ is promiscuous and bimodal: substrate-directed formation of quinolones versus quinazolinones. Angew Chem Int Ed Engl 60(15):8297–8302. https://doi.org/10.1002/anie.202017086
doi: 10.1002/anie.202017086 pubmed: 33411393 pmcid: 8049060
Elmagirbi A, Sulistyarti H, Atikah A (2012) Study of ascorbic acid as iron(III) reducing agent for spectrophotometric iron speciation. J Pure App Chem Res 1(1):11–17. https://doi.org/10.21776/ub.jpacr.2012.001.01.101
doi: 10.21776/ub.jpacr.2012.001.01.101
Gao SS, Naowarojna N, Cheng R, Liu X, Liu P (2018) Recent examples of alpha-ketoglutarate-dependent mononuclear non-haem iron enzymes in natural product biosyntheses. Nat Prod Rep 35:792–837. https://doi.org/10.1039/c7np00067g
doi: 10.1039/c7np00067g pubmed: 29932179 pmcid: 6093783
Gibson DG, Young L, Chuang RY, Venter JC, Hutchison CA 3rd, Smith HO (2009) Enzymatic assembly of DNA molecules up to several hundred kilobases. Nat Methods 6(5):343–345. https://doi.org/10.1038/nmeth.1318
doi: 10.1038/nmeth.1318 pubmed: 19363495
Havemann J, Vogel D, Loll B, Keller U (2014) Cyclolization of D-lysergic acid alkaloid peptides. Chem Biol 21(1):146–155. https://doi.org/10.1016/j.chembiol.2013.11.008
doi: 10.1016/j.chembiol.2013.11.008 pubmed: 24361048
Holland HL, Weber HK (2000) Enzymatic hydroxylation reactions. Curr Opin Biotechnol 11(6):547–553. https://doi.org/10.1016/S0958-1669(00)00142-7
doi: 10.1016/S0958-1669(00)00142-7 pubmed: 11102788
Ichimura T, Isobe T, Okuyama T, Takahashi N, Araki K, Kuwano R, Takahashi Y (1988) Molecular cloning of cDNA coding for brain-specific 14–3-3 protein, a protein kinase-dependent activator of tyrosine and tryptophan hydroxylases. Proc Natl Acad Sci U S A 85(19):7084–7088. https://doi.org/10.1073/pnas.85.19.7084
doi: 10.1073/pnas.85.19.7084 pubmed: 2902623 pmcid: 282128
Jakubczyk D, Caputi L, Hatsch A, Nielsen CA, Diefenbacher M, Klein J, Molt A, Schroder H, Cheng JZ, Naesby M, O’Connor SE (2015) Discovery and reconstitution of the cycloclavine biosynthetic pathway-enzymatic formation of a cyclopropyl group. Angew Chem (Weinheim Bergstrasse, Germany) 127(17):5206–5210. https://doi.org/10.1002/ange.201410002
doi: 10.1002/ange.201410002
Jakubczyk D, Caputi L, Stevenson CE, Lawson DM, O’Connor SE (2016) Structural characterization of EasH (Aspergillus japonicus) - an oxidase involved in cycloclavine biosynthesis. Chem Commun (Camb) 52(99):14306–14309. https://doi.org/10.1039/c6cc08438a
doi: 10.1039/c6cc08438a
Jakubczyk D, Cheng JZ, O’Connor SE (2014) Biosynthesis of the ergot alkaloids. Nat Prod Rep 31(10):1328–1338. https://doi.org/10.1039/c4np00062e
doi: 10.1039/c4np00062e pubmed: 25164781
Li S, Du L, Bernhardt R (2020) Redox partners: Function modulators of bacterial P450 enzymes. Trends Microbiol 28(6):445–454. https://doi.org/10.1016/j.tim.2020.02.012
doi: 10.1016/j.tim.2020.02.012 pubmed: 32396826
Liu H, Jia Y (2017) Ergot alkaloids: synthetic approaches to lysergic acid and clavine alkaloids. Nat Prod Rep 34(4):411–432. https://doi.org/10.1039/c6np00110f
doi: 10.1039/c6np00110f pubmed: 28300233
Lu H, Zhang XP (2011) Catalytic C-H functionalization by metalloporphyrins: recent developments and future directions. Chem Soc Rev 40(4):1899–1909. https://doi.org/10.1039/c0cs00070a
doi: 10.1039/c0cs00070a pubmed: 21088785
Martinez S, Hausinger RP (2015) Catalytic mechanisms of Fe(II)- and 2-oxoglutarate-dependent oxygenases. J Biol Chem 290(34):20702–20711. https://doi.org/10.1074/jbc.R115.648691
doi: 10.1074/jbc.R115.648691 pubmed: 26152721 pmcid: 4543632
Newhouse T, Baran PS (2011) If C-H bonds could talk: selective C-H bond oxidation. Angew Chem Int Ed Engl 50(15):3362–3374. https://doi.org/10.1002/anie.201006368
doi: 10.1002/anie.201006368 pubmed: 21413105 pmcid: 3980681
Schroeder H, Hoff B (2014) Gene cluster for biosyntheisis of cycloclavine. US Patent, Pub. No.: US 2014/0073008 A1
Wallwey C, Matuschek M, Xie XL, Li SM (2010) Ergot alkaloid biosynthesis in Aspergillus fumigatus: Conversion of chanoclavine-I aldehyde to festuclavine by the festuclavine synthase FgaFS in the presence of the old yellow enzyme FgaOx3. Organic Biomol Chem 8(15):3500–3508. https://doi.org/10.1039/c003823g
doi: 10.1039/c003823g
Yao Y, An C, Evans D, Liu W, Wang W, Wei G, Ding N, Houk KN, Gao SS (2019) Catalase involved in oxidative cyclization of the tetracyclic ergoline of fungal ergot alkaloids. J Am Chem Soc 141(44):17517–17521. https://doi.org/10.1021/jacs.9b10217
doi: 10.1021/jacs.9b10217 pubmed: 31621316 pmcid: 7592905
Yao Y, Wang W, Shi W, Yan R, Zhang J, Wei G, Liu L, Che Y, An C, Gao SS (2022) Overproduction of medicinal ergot alkaloids based on a fungal platform. Metab Eng 69:198–208. https://doi.org/10.1016/j.ymben.2021.12.002
doi: 10.1016/j.ymben.2021.12.002 pubmed: 34902590
Zheng C, You S-L (2014) Recent development of direct asymmetric functionalization of inert C-H bonds. RSC Adv 4(12):6173–6214. https://doi.org/10.1039/C3RA46996D
doi: 10.1039/C3RA46996D
Zhou Q, Peng SY, Zhang K, Luo GC, Han L, He QL, Tang GL (2021) A flavin-dependent monooxygenase mediates divergent oxidation of rifamycin. Org Lett 23(6):2342–2346. https://doi.org/10.1021/acs.orglett.1c00485
doi: 10.1021/acs.orglett.1c00485 pubmed: 33683897

Auteurs

Chunyan An (C)

Key Laboratory of Industrial Fermentation Microbiology of Ministry of Education, Biotechnology College of Tianjin University of Science and Technology, Tianjin, 300457, China. ancy@im.ac.cn.
State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, People's Republic of China. ancy@im.ac.cn.

Fangfang Zhu (F)

Key Laboratory of Industrial Fermentation Microbiology of Ministry of Education, Biotechnology College of Tianjin University of Science and Technology, Tianjin, 300457, China.
State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, People's Republic of China.

Yongpeng Yao (Y)

State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, People's Republic of China.

Kexin Zhang (K)

State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, People's Republic of China.
University of Chinese Academy of Sciences, Beijing, 100049, People's Republic of China.

Wei Wang (W)

State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, People's Republic of China.
University of Chinese Academy of Sciences, Beijing, 100049, People's Republic of China.

Jun Zhang (J)

State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, People's Republic of China.

Guangzheng Wei (G)

State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, People's Republic of China.
University of Chinese Academy of Sciences, Beijing, 100049, People's Republic of China.

Yue Xia (Y)

State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, People's Republic of China.

Qiang Gao (Q)

Key Laboratory of Industrial Fermentation Microbiology of Ministry of Education, Biotechnology College of Tianjin University of Science and Technology, Tianjin, 300457, China. gaoqiang@tust.edu.cn.

Shu-Shan Gao (SS)

State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, People's Republic of China. gaoss@im.ac.cn.

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