Renewable synthesis of n-butyraldehyde from glucose by engineered Escherichia coli

Abstract

Background n-Butyraldehyde is a high-production volume chemical produced exclusively from hydroformylation of propylene. It is a versatile chemical used in the synthesis of diverse C4–C8 alcohols, carboxylic acids, esters, and amines. Its high demand and broad applications make it an ideal chemical to be produced from biomass.ResultsAn Escherichia coli strain was engineered to produce n-butyraldehyde directly from glucose by expressing a modified Clostridium CoA-dependent n-butanol production pathway with mono-functional Coenzyme A-acylating aldehyde dehydrogenase (Aldh) instead of the natural bifunctional aldehyde/alcohol dehydrogenase. Aldh from Clostridium beijerinckii outperformed the other tested homologues. However, the presence of native alcohol dehydrogenase led to spontaneous conversion of n-butyraldehyde to n-butanol. This problem was addressed by knocking out native E. coli alcohol dehydrogenases, significantly improving the butyraldehyde-to-butanol ratio. This ratio was further increased reducing media complexity from Terrific broth to M9 media containing 2% yeast extract. To increase production titer, in situ liquid–liquid extraction using dodecane and oleyl alcohol was investigated. Results showed oleyl alcohol as a better extractant, increasing the titer of n-butyraldehyde produced to 630 mg/L.ConclusionThis study demonstrated n-butyraldehyde production from glucose. Through sequential strain and condition optimizations, butyraldehyde-to-butanol ratio was improved significantly compared to the parent strain. Results from this work may serve as a basis for further development of renewable n-butyraldehyde production.Electronic supplementary materialThe online version of this article (10.1186/s13068-017-0978-7) contains supplementary material, which is available to authorized users.

Escherichia coli as a host for metabolic engineering

“…Chemical feedstock BW25113 630 mg/L Expression of mono-functional aldehyde dehydrogenase instead of the conventional bi-functional aldehyde/alcohol dehydrogenase (Ku et al, 2017).…”

“…Intermediates of the Clostridial pathway have also been produced. The synthesis of butyraldehyde was achieved through replacing the bifunctional alcohol aldehyde dehydrogenase in the butanol pathway with a mono-functional aldehyde dehydrogenase (Ku et al, 2017). Butyraldehyde serves as a precursor to biological propane production (Kallio et al, 2014).…”

Photoautotrophic synthesis of butyrate by metabolically engineered cyanobacteria

“…Subsequently, butyryl‐CoA is converted to butyrate via butyryl‐phosphate. A synthetic chain elongation pathway extending acetyl‐CoA to butyryl‐CoA has been developed for efficient butanol (Bond‐Watts, Bellerose, & Chang, ; Shen et al, ) and butyraldehyde (Ku, Simanjuntak, & Lan, ) biosynthesis. However, we previously identified that thiolase, catalyzing the Claisen condensation of two acetyl‐CoA, is a major limiting step for cyanobacterial butanol production.…”

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO2 Utilization

“…[114d, 186] An ethoxylated version of 6d (EO-6d)w as pre-pared by allowing the growth of short oligo(ethylene oxide) chains on each hydroxy group of 6d followed by capping with ECH and carbonation. [187] As the latter aldehydes can be derived from bio-alcohols or from the fermentation of glucose, [188] 6d and 6e can be regarded as potentially renewable carbonates. [184] Trimethylolpropane and pentaerythritol, used as reagents for the synthesis of 6d and 6e,respectively,can be prepared by the reactions of formaldehyde with n-butyraldehyde or acetaldehyde.…”

“…[184] Trimethylolpropane and pentaerythritol, used as reagents for the synthesis of 6d and 6e,respectively,can be prepared by the reactions of formaldehyde with n-butyraldehyde or acetaldehyde. [187] As the latter aldehydes can be derived from bio-alcohols or from the fermentation of glucose, [188] 6d and 6e can be regarded as potentially renewable carbonates. 6f can be prepared from glycerol and ECH.…”