Metabolic Engineering toward Sustainable Production of Nylon-6

Stefan C H J Turk; Wigard P. Kloosterman; Dennis K. Ninaber; Karin P A M Kolen; Julia Knutova; Erwin Suir; Martin Schürmann; Petronella C. Raemakers-Franken; Monika Müller; Stefaan M A De Wildeman; Leonie M. Raamsdonk; Ruud Van Der Pol; Liang Wu; Margarida F. Temudo; Rob A M Van Der Hoeven; Michiel Akeroyd; Roland E. Van Der Stoel; Henk J. Noorman; Roel A L Bovenberg; Axel C. Trefzer

doi:10.1021/acssynbio.5b00129

Metabolic Engineering toward Sustainable Production of Nylon-6

Stefan C H J Turk^*
, Wigard P. Kloosterman
, Dennis K. Ninaber
, Karin P A M Kolen
, Julia Knutova
, Erwin Suir
, Martin Schürmann
, Petronella C. Raemakers-Franken
, Monika Müller
, Stefaan M A De Wildeman
, Leonie M. Raamsdonk
, Ruud Van Der Pol
, Liang Wu
, Margarida F. Temudo
, Rob A M Van Der Hoeven
, Michiel Akeroyd
, Roland E. Van Der Stoel
, Henk J. Noorman
, Roel A L Bovenberg
, Axel C. Trefzer

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

1 Citation (Scopus)

Abstract

Nylon-6 is a bulk polymer used for many applications. It consists of the non-natural building block 6-aminocaproic acid, the linear form of caprolactam. Via a retro-synthetic approach, two synthetic pathways were identified for the fermentative production of 6-aminocaproic acid. Both pathways require yet unreported novel biocatalytic steps. We demonstrated proof of these bioconversions by in vitro enzyme assays with a set of selected candidate proteins expressed in Escherichia coli. One of the biosynthetic pathways starts with 2-oxoglutarate and contains bioconversions of the ketoacid elongation pathway known from methanogenic archaea. This pathway was selected for implementation in E. coli and yielded 6-aminocaproic acid at levels up to 160 mg/L in lab-scale batch fermentations. The total amount of 6-aminocaproic acid and related intermediates generated by this pathway exceeded 2 g/L in lab-scale fed-batch fermentations, indicating its potential for further optimization toward large-scale sustainable production of nylon-6.

Original language	English
Pages (from-to)	65-73
Number of pages	9
Journal	ACS Synthetic Biology
Volume	5
Issue number	1
DOIs	https://doi.org/10.1021/acssynbio.5b00129
Publication status	Published - 15 Jan 2016

Keywords

6-aminocaproic acid
adipate
caprolactam
metabolic engineering
nylon-6
α-ketopimelate

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10.1021/acssynbio.5b00129

29Final published version, 427 KBLicence: Taverne

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Turk, S. C. H. J., Kloosterman, W. P., Ninaber, D. K., Kolen, K. P. A. M., Knutova, J., Suir, E., Schürmann, M., Raemakers-Franken, P. C., Müller, M., De Wildeman, S. M. A., Raamsdonk, L. M., Van Der Pol, R., Wu, L., Temudo, M. F., Van Der Hoeven, R. A. M., Akeroyd, M., Van Der Stoel, R. E., Noorman, H. J., Bovenberg, R. A. L., & Trefzer, A. C. (2016). Metabolic Engineering toward Sustainable Production of Nylon-6. ACS Synthetic Biology, 5(1), 65-73. https://doi.org/10.1021/acssynbio.5b00129

@article{7b02c53c2e7e4480957957b47693b40a,

title = "Metabolic Engineering toward Sustainable Production of Nylon-6",

abstract = "Nylon-6 is a bulk polymer used for many applications. It consists of the non-natural building block 6-aminocaproic acid, the linear form of caprolactam. Via a retro-synthetic approach, two synthetic pathways were identified for the fermentative production of 6-aminocaproic acid. Both pathways require yet unreported novel biocatalytic steps. We demonstrated proof of these bioconversions by in vitro enzyme assays with a set of selected candidate proteins expressed in Escherichia coli. One of the biosynthetic pathways starts with 2-oxoglutarate and contains bioconversions of the ketoacid elongation pathway known from methanogenic archaea. This pathway was selected for implementation in E. coli and yielded 6-aminocaproic acid at levels up to 160 mg/L in lab-scale batch fermentations. The total amount of 6-aminocaproic acid and related intermediates generated by this pathway exceeded 2 g/L in lab-scale fed-batch fermentations, indicating its potential for further optimization toward large-scale sustainable production of nylon-6.",

keywords = "6-aminocaproic acid, adipate, caprolactam, metabolic engineering, nylon-6, α-ketopimelate",

author = "Turk, \{Stefan C H J\} and Kloosterman, \{Wigard P.\} and Ninaber, \{Dennis K.\} and Kolen, \{Karin P A M\} and Julia Knutova and Erwin Suir and Martin Sch{\"u}rmann and Raemakers-Franken, \{Petronella C.\} and Monika M{\"u}ller and \{De Wildeman\}, \{Stefaan M A\} and Raamsdonk, \{Leonie M.\} and \{Van Der Pol\}, Ruud and Liang Wu and Temudo, \{Margarida F.\} and \{Van Der Hoeven\}, \{Rob A M\} and Michiel Akeroyd and \{Van Der Stoel\}, \{Roland E.\} and Noorman, \{Henk J.\} and Bovenberg, \{Roel A L\} and Trefzer, \{Axel C.\}",

year = "2016",

month = jan,

day = "15",

doi = "10.1021/acssynbio.5b00129",

language = "English",

volume = "5",

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journal = "ACS Synthetic Biology",

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publisher = "American Chemical Society",

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Turk, SCHJ, Kloosterman, WP, Ninaber, DK, Kolen, KPAM, Knutova, J, Suir, E, Schürmann, M, Raemakers-Franken, PC, Müller, M, De Wildeman, SMA, Raamsdonk, LM, Van Der Pol, R, Wu, L, Temudo, MF, Van Der Hoeven, RAM, Akeroyd, M, Van Der Stoel, RE, Noorman, HJ, Bovenberg, RAL & Trefzer, AC 2016, 'Metabolic Engineering toward Sustainable Production of Nylon-6', ACS Synthetic Biology, vol. 5, no. 1, pp. 65-73. https://doi.org/10.1021/acssynbio.5b00129

TY - JOUR

T1 - Metabolic Engineering toward Sustainable Production of Nylon-6

AU - Turk, Stefan C H J

AU - Kloosterman, Wigard P.

AU - Ninaber, Dennis K.

AU - Kolen, Karin P A M

AU - Knutova, Julia

AU - Suir, Erwin

AU - Schürmann, Martin

AU - Raemakers-Franken, Petronella C.

AU - Müller, Monika

AU - De Wildeman, Stefaan M A

AU - Raamsdonk, Leonie M.

AU - Van Der Pol, Ruud

AU - Wu, Liang

AU - Temudo, Margarida F.

AU - Van Der Hoeven, Rob A M

AU - Akeroyd, Michiel

AU - Van Der Stoel, Roland E.

AU - Noorman, Henk J.

AU - Bovenberg, Roel A L

AU - Trefzer, Axel C.

PY - 2016/1/15

Y1 - 2016/1/15

N2 - Nylon-6 is a bulk polymer used for many applications. It consists of the non-natural building block 6-aminocaproic acid, the linear form of caprolactam. Via a retro-synthetic approach, two synthetic pathways were identified for the fermentative production of 6-aminocaproic acid. Both pathways require yet unreported novel biocatalytic steps. We demonstrated proof of these bioconversions by in vitro enzyme assays with a set of selected candidate proteins expressed in Escherichia coli. One of the biosynthetic pathways starts with 2-oxoglutarate and contains bioconversions of the ketoacid elongation pathway known from methanogenic archaea. This pathway was selected for implementation in E. coli and yielded 6-aminocaproic acid at levels up to 160 mg/L in lab-scale batch fermentations. The total amount of 6-aminocaproic acid and related intermediates generated by this pathway exceeded 2 g/L in lab-scale fed-batch fermentations, indicating its potential for further optimization toward large-scale sustainable production of nylon-6.

AB - Nylon-6 is a bulk polymer used for many applications. It consists of the non-natural building block 6-aminocaproic acid, the linear form of caprolactam. Via a retro-synthetic approach, two synthetic pathways were identified for the fermentative production of 6-aminocaproic acid. Both pathways require yet unreported novel biocatalytic steps. We demonstrated proof of these bioconversions by in vitro enzyme assays with a set of selected candidate proteins expressed in Escherichia coli. One of the biosynthetic pathways starts with 2-oxoglutarate and contains bioconversions of the ketoacid elongation pathway known from methanogenic archaea. This pathway was selected for implementation in E. coli and yielded 6-aminocaproic acid at levels up to 160 mg/L in lab-scale batch fermentations. The total amount of 6-aminocaproic acid and related intermediates generated by this pathway exceeded 2 g/L in lab-scale fed-batch fermentations, indicating its potential for further optimization toward large-scale sustainable production of nylon-6.

KW - 6-aminocaproic acid

KW - adipate

KW - caprolactam

KW - metabolic engineering

KW - nylon-6

KW - α-ketopimelate

UR - https://www.scopus.com/pages/publications/84954409658

U2 - 10.1021/acssynbio.5b00129

DO - 10.1021/acssynbio.5b00129

M3 - Article

C2 - 26511532

AN - SCOPUS:84954409658

SN - 2161-5063

VL - 5

SP - 65

EP - 73

JO - ACS Synthetic Biology

JF - ACS Synthetic Biology

IS - 1

ER -

Metabolic Engineering toward Sustainable Production of Nylon-6

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Keywords

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