Hydroperoxide production from linoleic acid by heterologous Gaeumannomyces graminis tritici lipoxygenase: Optimization and scale-up

J.J. Villaverde (Corresponding Author), V. van der Vlist, S.A.O. Santos, T. Haarmann, K. Langfelder, Minni Pirttimaa, Antti Nyyssölä, Sirpa Jylhä, Tarja Tamminen, Kristiina Kruus, L. de Graaff, C.P. Neto, M.M.Q. Simoes, M.R.M. Domingues, A.J.D. Silvestre, J. Eidner, Johanna Buchert

Research output: Contribution to journalArticleScientificpeer-review

20 Citations (Scopus)

Abstract

Linoleic acid was converted into hydroperoxides by a Gaeumannomyces graminis tritici lipoxygenase produced recombinantly in Trichoderma reesei. Hydroperoxide production was optimized using a face-centred experimental design in order to study the effects of pH, temperature and time on the conversion of linoleic acid into four regioisomeric hydroperoxyoctadecadienoic acids (HPODE): 13-(Z,E)-, 9-(E,Z)-, 13-(E,E)-, 9-(E,E)-HPODE. Fitting equations described satisfactorily the system behavior and showed that reaction time was the most influencing independent variable. A set of independent variables (pH = 6.7, temperature = 23.9 °C and time = 18 h) allowed to obtain high yields of hydroperoxides (88.0%) with a good selectivity for the 13-(Z,E)-HPODE isomer (47.4%) when the initial substrate concentration was 10 g/L. The production was further investigated using industrially relevant linoleic acid concentrations (100–300 g/L) leading to HPODE yields of ∼40% and the volumetric productivity 3.6 g/(L h), and a selectivity for 13-(Z,E)-HPODE of around 74%.
Original languageEnglish
Pages (from-to)82-90
Number of pages9
JournalChemical Engineering Journal
Volume217
DOIs
Publication statusPublished - 2013
MoE publication typeA1 Journal article-refereed

Fingerprint

Linoleic acid
Lipoxygenase
Linoleic Acid
Hydrogen Peroxide
Acids
acid
Isomers
Design of experiments
Productivity
Temperature
experimental design
Substrates
temperature
substrate
productivity

Keywords

  • Fatty acid hydroperoxides
  • linoleic acid
  • lipoxygenase
  • optimization
  • scale-up

Cite this

Villaverde, J. J., van der Vlist, V., Santos, S. A. O., Haarmann, T., Langfelder, K., Pirttimaa, M., ... Buchert, J. (2013). Hydroperoxide production from linoleic acid by heterologous Gaeumannomyces graminis tritici lipoxygenase: Optimization and scale-up. Chemical Engineering Journal, 217, 82-90. https://doi.org/10.1016/j.cej.2012.11.090
Villaverde, J.J. ; van der Vlist, V. ; Santos, S.A.O. ; Haarmann, T. ; Langfelder, K. ; Pirttimaa, Minni ; Nyyssölä, Antti ; Jylhä, Sirpa ; Tamminen, Tarja ; Kruus, Kristiina ; de Graaff, L. ; Neto, C.P. ; Simoes, M.M.Q. ; Domingues, M.R.M. ; Silvestre, A.J.D. ; Eidner, J. ; Buchert, Johanna. / Hydroperoxide production from linoleic acid by heterologous Gaeumannomyces graminis tritici lipoxygenase : Optimization and scale-up. In: Chemical Engineering Journal. 2013 ; Vol. 217. pp. 82-90.
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title = "Hydroperoxide production from linoleic acid by heterologous Gaeumannomyces graminis tritici lipoxygenase: Optimization and scale-up",
abstract = "Linoleic acid was converted into hydroperoxides by a Gaeumannomyces graminis tritici lipoxygenase produced recombinantly in Trichoderma reesei. Hydroperoxide production was optimized using a face-centred experimental design in order to study the effects of pH, temperature and time on the conversion of linoleic acid into four regioisomeric hydroperoxyoctadecadienoic acids (HPODE): 13-(Z,E)-, 9-(E,Z)-, 13-(E,E)-, 9-(E,E)-HPODE. Fitting equations described satisfactorily the system behavior and showed that reaction time was the most influencing independent variable. A set of independent variables (pH = 6.7, temperature = 23.9 °C and time = 18 h) allowed to obtain high yields of hydroperoxides (88.0{\%}) with a good selectivity for the 13-(Z,E)-HPODE isomer (47.4{\%}) when the initial substrate concentration was 10 g/L. The production was further investigated using industrially relevant linoleic acid concentrations (100–300 g/L) leading to HPODE yields of ∼40{\%} and the volumetric productivity 3.6 g/(L h), and a selectivity for 13-(Z,E)-HPODE of around 74{\%}.",
keywords = "Fatty acid hydroperoxides, linoleic acid, lipoxygenase, optimization, scale-up",
author = "J.J. Villaverde and {van der Vlist}, V. and S.A.O. Santos and T. Haarmann and K. Langfelder and Minni Pirttimaa and Antti Nyyss{\"o}l{\"a} and Sirpa Jylh{\"a} and Tarja Tamminen and Kristiina Kruus and {de Graaff}, L. and C.P. Neto and M.M.Q. Simoes and M.R.M. Domingues and A.J.D. Silvestre and J. Eidner and Johanna Buchert",
year = "2013",
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Villaverde, JJ, van der Vlist, V, Santos, SAO, Haarmann, T, Langfelder, K, Pirttimaa, M, Nyyssölä, A, Jylhä, S, Tamminen, T, Kruus, K, de Graaff, L, Neto, CP, Simoes, MMQ, Domingues, MRM, Silvestre, AJD, Eidner, J & Buchert, J 2013, 'Hydroperoxide production from linoleic acid by heterologous Gaeumannomyces graminis tritici lipoxygenase: Optimization and scale-up', Chemical Engineering Journal, vol. 217, pp. 82-90. https://doi.org/10.1016/j.cej.2012.11.090

Hydroperoxide production from linoleic acid by heterologous Gaeumannomyces graminis tritici lipoxygenase : Optimization and scale-up. / Villaverde, J.J. (Corresponding Author); van der Vlist, V.; Santos, S.A.O.; Haarmann, T.; Langfelder, K.; Pirttimaa, Minni; Nyyssölä, Antti; Jylhä, Sirpa; Tamminen, Tarja; Kruus, Kristiina; de Graaff, L.; Neto, C.P.; Simoes, M.M.Q.; Domingues, M.R.M.; Silvestre, A.J.D.; Eidner, J.; Buchert, Johanna.

In: Chemical Engineering Journal, Vol. 217, 2013, p. 82-90.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Hydroperoxide production from linoleic acid by heterologous Gaeumannomyces graminis tritici lipoxygenase

T2 - Optimization and scale-up

AU - Villaverde, J.J.

AU - van der Vlist, V.

AU - Santos, S.A.O.

AU - Haarmann, T.

AU - Langfelder, K.

AU - Pirttimaa, Minni

AU - Nyyssölä, Antti

AU - Jylhä, Sirpa

AU - Tamminen, Tarja

AU - Kruus, Kristiina

AU - de Graaff, L.

AU - Neto, C.P.

AU - Simoes, M.M.Q.

AU - Domingues, M.R.M.

AU - Silvestre, A.J.D.

AU - Eidner, J.

AU - Buchert, Johanna

PY - 2013

Y1 - 2013

N2 - Linoleic acid was converted into hydroperoxides by a Gaeumannomyces graminis tritici lipoxygenase produced recombinantly in Trichoderma reesei. Hydroperoxide production was optimized using a face-centred experimental design in order to study the effects of pH, temperature and time on the conversion of linoleic acid into four regioisomeric hydroperoxyoctadecadienoic acids (HPODE): 13-(Z,E)-, 9-(E,Z)-, 13-(E,E)-, 9-(E,E)-HPODE. Fitting equations described satisfactorily the system behavior and showed that reaction time was the most influencing independent variable. A set of independent variables (pH = 6.7, temperature = 23.9 °C and time = 18 h) allowed to obtain high yields of hydroperoxides (88.0%) with a good selectivity for the 13-(Z,E)-HPODE isomer (47.4%) when the initial substrate concentration was 10 g/L. The production was further investigated using industrially relevant linoleic acid concentrations (100–300 g/L) leading to HPODE yields of ∼40% and the volumetric productivity 3.6 g/(L h), and a selectivity for 13-(Z,E)-HPODE of around 74%.

AB - Linoleic acid was converted into hydroperoxides by a Gaeumannomyces graminis tritici lipoxygenase produced recombinantly in Trichoderma reesei. Hydroperoxide production was optimized using a face-centred experimental design in order to study the effects of pH, temperature and time on the conversion of linoleic acid into four regioisomeric hydroperoxyoctadecadienoic acids (HPODE): 13-(Z,E)-, 9-(E,Z)-, 13-(E,E)-, 9-(E,E)-HPODE. Fitting equations described satisfactorily the system behavior and showed that reaction time was the most influencing independent variable. A set of independent variables (pH = 6.7, temperature = 23.9 °C and time = 18 h) allowed to obtain high yields of hydroperoxides (88.0%) with a good selectivity for the 13-(Z,E)-HPODE isomer (47.4%) when the initial substrate concentration was 10 g/L. The production was further investigated using industrially relevant linoleic acid concentrations (100–300 g/L) leading to HPODE yields of ∼40% and the volumetric productivity 3.6 g/(L h), and a selectivity for 13-(Z,E)-HPODE of around 74%.

KW - Fatty acid hydroperoxides

KW - linoleic acid

KW - lipoxygenase

KW - optimization

KW - scale-up

U2 - 10.1016/j.cej.2012.11.090

DO - 10.1016/j.cej.2012.11.090

M3 - Article

VL - 217

SP - 82

EP - 90

JO - Chemical Engineering Journal

JF - Chemical Engineering Journal

SN - 1385-8947

ER -