Improving catalytic activity of the Baeyer–Villiger monooxygenase-based Escherichia coli biocatalysts for the overproduction of (Z)-11-(heptanoyloxy)undec-9-enoic acid from ricinoleic acid

Abstract Baeyer–Villiger monooxygenases (BVMOs) can be used for the biosynthesis of lactones and esters from ketones. However, the BVMO-based biocatalysts are not so stable under process conditions. Thereby, this study focused on enhancing stability of the BVMO-based biocatalysts. The biotransformat...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Ji-Min Woo, Eun-Yeong Jeon, Eun-Ji Seo, Joo-Hyun Seo, Dong-Yup Lee, Young Joo Yeon, Jin-Byung Park
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2018
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/798a8107b85d4efabf5957a7c2422088
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:798a8107b85d4efabf5957a7c2422088
record_format	dspace
spelling	oai:doaj.org-article:798a8107b85d4efabf5957a7c24220882021-12-02T15:07:51ZImproving catalytic activity of the Baeyer–Villiger monooxygenase-based Escherichia coli biocatalysts for the overproduction of (Z)-11-(heptanoyloxy)undec-9-enoic acid from ricinoleic acid10.1038/s41598-018-28575-82045-2322https://doaj.org/article/798a8107b85d4efabf5957a7c24220882018-07-01T00:00:00Zhttps://doi.org/10.1038/s41598-018-28575-8https://doaj.org/toc/2045-2322Abstract Baeyer–Villiger monooxygenases (BVMOs) can be used for the biosynthesis of lactones and esters from ketones. However, the BVMO-based biocatalysts are not so stable under process conditions. Thereby, this study focused on enhancing stability of the BVMO-based biocatalysts. The biotransformation of ricinoleic acid into (Z)-11-(heptanoyloxy)undec-9-enoic acid by the recombinant Escherichia coli expressing the BVMO from Pseudomonas putida and an alcohol dehydrogenase from Micrococcus luteus was used as a model system. After thorough investigation of the key factors to influence stability of the BVMO, Cys302 was identified as an engineering target. The substitution of Cys302 to Leu enabled the engineered enzyme (i.e., E6BVMOC302L) to become more stable toward oxidative and thermal stresses. The catalytic activity of E6BVMOC302L-based E. coli biocatalysts was also greater than the E6BVMO-based biocatalysts. Another factor to influence biocatalytic performance of the BVMO-based whole-cell biocatalysts was availability of carbon and energy source during biotransformations. Glucose feeding into the reaction medium led to a marked increase of final product concentrations. Overall, the bioprocess engineering to improve metabolic stability of host cells in addition to the BVMO engineering allowed us to produce (Z)-11-(heptanoyloxy)undec-9-enoic acid to a concentration of 132 mM (41 g/L) from 150 mM ricinoleic acid within 8 h.Ji-Min WooEun-Yeong JeonEun-Ji SeoJoo-Hyun SeoDong-Yup LeeYoung Joo YeonJin-Byung ParkNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 8, Iss 1, Pp 1-11 (2018)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Ji-Min Woo Eun-Yeong Jeon Eun-Ji Seo Joo-Hyun Seo Dong-Yup Lee Young Joo Yeon Jin-Byung Park Improving catalytic activity of the Baeyer–Villiger monooxygenase-based Escherichia coli biocatalysts for the overproduction of (Z)-11-(heptanoyloxy)undec-9-enoic acid from ricinoleic acid
description	Abstract Baeyer–Villiger monooxygenases (BVMOs) can be used for the biosynthesis of lactones and esters from ketones. However, the BVMO-based biocatalysts are not so stable under process conditions. Thereby, this study focused on enhancing stability of the BVMO-based biocatalysts. The biotransformation of ricinoleic acid into (Z)-11-(heptanoyloxy)undec-9-enoic acid by the recombinant Escherichia coli expressing the BVMO from Pseudomonas putida and an alcohol dehydrogenase from Micrococcus luteus was used as a model system. After thorough investigation of the key factors to influence stability of the BVMO, Cys302 was identified as an engineering target. The substitution of Cys302 to Leu enabled the engineered enzyme (i.e., E6BVMOC302L) to become more stable toward oxidative and thermal stresses. The catalytic activity of E6BVMOC302L-based E. coli biocatalysts was also greater than the E6BVMO-based biocatalysts. Another factor to influence biocatalytic performance of the BVMO-based whole-cell biocatalysts was availability of carbon and energy source during biotransformations. Glucose feeding into the reaction medium led to a marked increase of final product concentrations. Overall, the bioprocess engineering to improve metabolic stability of host cells in addition to the BVMO engineering allowed us to produce (Z)-11-(heptanoyloxy)undec-9-enoic acid to a concentration of 132 mM (41 g/L) from 150 mM ricinoleic acid within 8 h.
format	article
author	Ji-Min Woo Eun-Yeong Jeon Eun-Ji Seo Joo-Hyun Seo Dong-Yup Lee Young Joo Yeon Jin-Byung Park
author_facet	Ji-Min Woo Eun-Yeong Jeon Eun-Ji Seo Joo-Hyun Seo Dong-Yup Lee Young Joo Yeon Jin-Byung Park
author_sort	Ji-Min Woo
title	Improving catalytic activity of the Baeyer–Villiger monooxygenase-based Escherichia coli biocatalysts for the overproduction of (Z)-11-(heptanoyloxy)undec-9-enoic acid from ricinoleic acid
title_short	Improving catalytic activity of the Baeyer–Villiger monooxygenase-based Escherichia coli biocatalysts for the overproduction of (Z)-11-(heptanoyloxy)undec-9-enoic acid from ricinoleic acid
title_full	Improving catalytic activity of the Baeyer–Villiger monooxygenase-based Escherichia coli biocatalysts for the overproduction of (Z)-11-(heptanoyloxy)undec-9-enoic acid from ricinoleic acid
title_fullStr	Improving catalytic activity of the Baeyer–Villiger monooxygenase-based Escherichia coli biocatalysts for the overproduction of (Z)-11-(heptanoyloxy)undec-9-enoic acid from ricinoleic acid
title_full_unstemmed	Improving catalytic activity of the Baeyer–Villiger monooxygenase-based Escherichia coli biocatalysts for the overproduction of (Z)-11-(heptanoyloxy)undec-9-enoic acid from ricinoleic acid
title_sort	improving catalytic activity of the baeyer–villiger monooxygenase-based escherichia coli biocatalysts for the overproduction of (z)-11-(heptanoyloxy)undec-9-enoic acid from ricinoleic acid
publisher	Nature Portfolio
publishDate	2018
url	https://doaj.org/article/798a8107b85d4efabf5957a7c2422088
work_keys_str_mv	AT jiminwoo improvingcatalyticactivityofthebaeyervilligermonooxygenasebasedescherichiacolibiocatalystsfortheoverproductionofz11heptanoyloxyundec9enoicacidfromricinoleicacid AT eunyeongjeon improvingcatalyticactivityofthebaeyervilligermonooxygenasebasedescherichiacolibiocatalystsfortheoverproductionofz11heptanoyloxyundec9enoicacidfromricinoleicacid AT eunjiseo improvingcatalyticactivityofthebaeyervilligermonooxygenasebasedescherichiacolibiocatalystsfortheoverproductionofz11heptanoyloxyundec9enoicacidfromricinoleicacid AT joohyunseo improvingcatalyticactivityofthebaeyervilligermonooxygenasebasedescherichiacolibiocatalystsfortheoverproductionofz11heptanoyloxyundec9enoicacidfromricinoleicacid AT dongyuplee improvingcatalyticactivityofthebaeyervilligermonooxygenasebasedescherichiacolibiocatalystsfortheoverproductionofz11heptanoyloxyundec9enoicacidfromricinoleicacid AT youngjooyeon improvingcatalyticactivityofthebaeyervilligermonooxygenasebasedescherichiacolibiocatalystsfortheoverproductionofz11heptanoyloxyundec9enoicacidfromricinoleicacid AT jinbyungpark improvingcatalyticactivityofthebaeyervilligermonooxygenasebasedescherichiacolibiocatalystsfortheoverproductionofz11heptanoyloxyundec9enoicacidfromricinoleicacid
_version_	1718388395986649088

Improving catalytic activity of the Baeyer–Villiger monooxygenase-based Escherichia coli biocatalysts for the overproduction of (Z)-11-(heptanoyloxy)undec-9-enoic acid from ricinoleic acid

Ejemplares similares