Efficient epoxidation of (R)-(+)-limonene to limonene dioxide through peracids generated using whole-cell Rhizopus oryzae lipase.

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  • Additional Information
    • Source:
      Publisher: Elsevier Applied Science Country of Publication: England NLM ID: 9889523 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1873-2976 (Electronic) Linking ISSN: 09608524 NLM ISO Abbreviation: Bioresour Technol Subsets: MEDLINE
    • Publication Information:
      Original Publication: Barking, Essex, England : New York, N.Y. : Elsevier Applied Science ; Elsevier Science Pub. Co., 1991-
    • Subject Terms:
      Limonene*/pharmacology ; Terpenes*/metabolism ; Terpenes*/chemistry ; Cyclohexenes*/chemistry ; Cyclohexenes*/metabolism ; Lipase*/metabolism ; Rhizopus oryzae*/metabolism ; Hydrogen Peroxide*/chemistry; Epoxy Compounds/chemistry ; Oxides/chemistry ; Fungal Proteins/metabolism
    • Abstract:
      Limonene dioxide (LDO) is essential for manufacturing bio-based polycarbonate and non-isocyanate polyurethanes. Herein, we report a strategy for the chemoenzymatic epoxidation of (R)-(+)-limonene to LDO with high selectivity using Rhizopus oryzae whole cells. The presence of sufficient excess acid in the system is essential, in addition to overcoming the hydrolysis of the intermediate product, 1,2-limonene oxide, to accomplish the double epoxidation of limonene. When using a high concentration of H 2 O 2 and trisodium citrate, the conditions were effectively established, even when Novozym 435 was substituted, which had previously been reported to be ineffective in achieving high-yield double epoxidation of limonene. The transfer of H 2 O 2 and peracids between the cell and solvent slowed production. The total amount of peracids generated remained constant, but their concentrations remained moderate, favoring the double epoxidation of limonene. An LDO yield of 93 % and no intermediate product, limonene oxide, were obtained under optimized conditions within 20 h.
      Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
      (Copyright © 2024. Published by Elsevier Ltd.)
    • Contributed Indexing:
      Keywords: Chemoenzymatic epoxidation; Limonene; Limonene dioxide; Peroxy acid; Rhizopus oryzae; Whole cell
    • Accession Number:
      9MC3I34447 (Limonene)
      0 (Terpenes)
      0 (Cyclohexenes)
      EC 3.1.1.3 (Lipase)
      BBX060AN9V (Hydrogen Peroxide)
      0 (Epoxy Compounds)
      0 (Oxides)
      0 (Fungal Proteins)
    • Publication Date:
      Date Created: 20241017 Date Completed: 20241115 Latest Revision: 20241115
    • Publication Date:
      20241116
    • Accession Number:
      10.1016/j.biortech.2024.131645
    • Accession Number:
      39419407