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Article

Synthesis of Ferulenol by Engineered Escherichia coli: Structural Elucidation by Using the In Silico Tools

1
Faculty of Pharmaceutical Sciences, Khon Kaen University, Khon Kaen 40002, Thailand
2
Salaya Central Instrument Facility RSPG, Research Management and Development Division, Office of the President, Mahidol University, Nakhon Pathom 73170, Thailand
*
Author to whom correspondence should be addressed.
Academic Editors: Maria João Matos and Valeria Costantino
Molecules 2021, 26(20), 6264; https://doi.org/10.3390/molecules26206264
Received: 11 July 2021 / Revised: 26 September 2021 / Accepted: 13 October 2021 / Published: 16 October 2021
(This article belongs to the Special Issue Coumarin and Its Derivatives)
4-Hydroxycoumarin (4HC) has been used as a lead compound for the chemical synthesis of various bioactive substances and drugs. Its prenylated derivatives exhibit potent antibacterial, antitubercular, anticoagulant, and anti-cancer activities. In doing this, E. coli BL21(DE3)pLysS strain was engineered as the in vivo prenylation system to produce the farnesyl derivatives of 4HC by coexpressing the genes encoding Aspergillus terreus aromatic prenyltransferase (AtaPT) and truncated 1-deoxy-D-xylose 5-phosphate synthase of Croton stellatopilosus (CstDXS), where 4HC was the fed precursor. Based on the high-resolution LC-ESI(±)-QTOF-MS/MS with the use of in silico tools (e.g., MetFrag, SIRIUS (version 4.8.2), CSI:FingerID, and CANOPUS), the first major prenylated product (named compound-1) was detected and ultimately elucidated as ferulenol, in which information concerning the correct molecular formula, chemical structure, substructures, and classifications were obtained. The prenylated product (named compound-2) was also detected as the minor product, where this structure proposed to be the isomeric structure of ferulenol formed via the tautomerization. Note that both products were secreted into the culture medium of the recombinant E. coli and could be produced without the external supply of prenyl precursors. The results suggested the potential use of this engineered pathway for synthesizing the farnesylated-4HC derivatives, especially ferulenol. View Full-Text
Keywords: Escherichia coli; biotransformation; 4-hydroxycoumarin; ferulenol; structural annotation; in silico tools Escherichia coli; biotransformation; 4-hydroxycoumarin; ferulenol; structural annotation; in silico tools
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MDPI and ACS Style

Klamrak, A.; Nabnueangsap, J.; Puthongking, P.; Nualkaew, N. Synthesis of Ferulenol by Engineered Escherichia coli: Structural Elucidation by Using the In Silico Tools. Molecules 2021, 26, 6264. https://doi.org/10.3390/molecules26206264

AMA Style

Klamrak A, Nabnueangsap J, Puthongking P, Nualkaew N. Synthesis of Ferulenol by Engineered Escherichia coli: Structural Elucidation by Using the In Silico Tools. Molecules. 2021; 26(20):6264. https://doi.org/10.3390/molecules26206264

Chicago/Turabian Style

Klamrak, Anuwatchakij, Jaran Nabnueangsap, Ploenthip Puthongking, and Natsajee Nualkaew. 2021. "Synthesis of Ferulenol by Engineered Escherichia coli: Structural Elucidation by Using the In Silico Tools" Molecules 26, no. 20: 6264. https://doi.org/10.3390/molecules26206264

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