From a Biosynthetic Pathway toward a Biocatalytic Process and Chemocatalytic Modifications: Three‐Step Enzymatic Cascade to the Plant Metabolite cis ‐(+)‐12‐OPDA and Metathesis‐Derived Products

Löwe J, Dietz K-J, Gröger H (2020)
Advanced Science 7(13): 1902973.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
A biotechnological approach toward the plant metabolite and regulator cis‐(+)‐12‐oxophytodienoic acid (cis‐(+)‐12‐OPDA) in a one‐pot process with >99% conversion, at least 90% selectivity and ≤10% of side products as well as a high diastereoselectivity (leading to d.r. of at least 90:10) is reported. The optimized organic‐synthetic enzyme cascade for preparing this bioactive and commercial molecule with pharmaceutical relevance on a gram per L scale is designed based on its biosynthetic pathway starting from cheap and readily accessible linolenic acid. Toward this end, a recombinant biocatalyst system has been prepared for carrying out the most critical two key steps in a tailored manner, thus avoiding sensitive intermediate decomposition. Furthermore, cis‐(+)‐12‐OPDA is successfully modified via a cross‐alkene metathesis reaction with conversions of up to >99%, leading to a compound library of new cis‐(+)‐12‐OPDA derivatives with different substitution pattern of the side chain at the 2‐position. By means of such a combined biotechnological and chemocatalytic route, a straightforward approach to a structurally unique oxylipin library is realized, which would be highly difficult or not accessible by pure chemical and biotechnological methods, respectively.
Stichworte
General Engineering; General Physics and Astronomy; General Materials Science; Medicine (miscellaneous); General Chemical Engineering; Biochemistry; Genetics and Molecular Biology (miscellaneous)
Erscheinungsjahr
2020
Zeitschriftentitel
Advanced Science
Band
7
Ausgabe
13
Art.-Nr.
1902973
eISSN
2198-3844
Page URI
https://pub.uni-bielefeld.de/record/2944582

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Löwe J, Dietz K-J, Gröger H. From a Biosynthetic Pathway toward a Biocatalytic Process and Chemocatalytic Modifications: Three‐Step Enzymatic Cascade to the Plant Metabolite cis ‐(+)‐12‐OPDA and Metathesis‐Derived Products. Advanced Science. 2020;7(13): 1902973.
Löwe, J., Dietz, K. - J., & Gröger, H. (2020). From a Biosynthetic Pathway toward a Biocatalytic Process and Chemocatalytic Modifications: Three‐Step Enzymatic Cascade to the Plant Metabolite cis ‐(+)‐12‐OPDA and Metathesis‐Derived Products. Advanced Science, 7(13), 1902973. doi:10.1002/advs.201902973
Löwe, J., Dietz, K. - J., and Gröger, H. (2020). From a Biosynthetic Pathway toward a Biocatalytic Process and Chemocatalytic Modifications: Three‐Step Enzymatic Cascade to the Plant Metabolite cis ‐(+)‐12‐OPDA and Metathesis‐Derived Products. Advanced Science 7:1902973.
Löwe, J., Dietz, K.-J., & Gröger, H., 2020. From a Biosynthetic Pathway toward a Biocatalytic Process and Chemocatalytic Modifications: Three‐Step Enzymatic Cascade to the Plant Metabolite cis ‐(+)‐12‐OPDA and Metathesis‐Derived Products. Advanced Science, 7(13): 1902973.
J. Löwe, K.-J. Dietz, and H. Gröger, “From a Biosynthetic Pathway toward a Biocatalytic Process and Chemocatalytic Modifications: Three‐Step Enzymatic Cascade to the Plant Metabolite cis ‐(+)‐12‐OPDA and Metathesis‐Derived Products”, Advanced Science, vol. 7, 2020, : 1902973.
Löwe, J., Dietz, K.-J., Gröger, H.: From a Biosynthetic Pathway toward a Biocatalytic Process and Chemocatalytic Modifications: Three‐Step Enzymatic Cascade to the Plant Metabolite cis ‐(+)‐12‐OPDA and Metathesis‐Derived Products. Advanced Science. 7, : 1902973 (2020).
Löwe, Jana, Dietz, Karl-Josef, and Gröger, Harald. “From a Biosynthetic Pathway toward a Biocatalytic Process and Chemocatalytic Modifications: Three‐Step Enzymatic Cascade to the Plant Metabolite cis ‐(+)‐12‐OPDA and Metathesis‐Derived Products”. Advanced Science 7.13 (2020): 1902973.
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