Microbial production of sebacic acid from a renewable source: production, purification, and polymerization

Jeon, Wooyoung; Jang, Min-Jeong; Park, Gyuyeon; Lee, Hye Jeong; Seo, Sunghwa; Lee, Hee-Suk; Han, Changpyo; Kwon, Heeun; Lee, Ho-Chang; Lee, Jong-Hwa; Hwang, Youn‐Ho; Lee, Myung-Ock; Lee, Jeong-Gyu; Lee, Hongweon; Ahn, Jungoh

doi:10.1039/c9gc02274k

Cited by 23 publications

(16 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Mono- and polycarboxylic acids (mono- and poly-CAs) are ubiquitous in nature and represent a large repository of platform chemical precursors . Several reports have shown that CAs can be derived from biomass-based resources such as lignin and hemicellulose using green and economically feasible methods. , Likewise, many different methods for producing dicarboxylic acids (di-CAs) from biomass have been developed. − Although the produced CAs are valuable by themselves, their corresponding terminal alcohols (ALs) are more interesting as platform chemicals, as they may find useful applications in the production of polymers and as fuel additives to improve the octane number. Moreover, terminal ALs are in general synthetically more useful than the parent CAs.…”

Section: Introductionmentioning

confidence: 99%

Selective Reduction of Carboxylic Acids to Alcohols in the Presence of Alcohols by a Dual Bulky Transition-Metal Complex/Lewis Acid Catalyst

2022

View full text Add to dashboard Cite

Here, we report a molecular method for the generally applicable reduction of mono- and dicarboxylic acids that selectively furnishes a diverse variety of alcohols, including mono- and diols. One of the inherent drawbacks of the direct hydrogenation of carboxylic acids to alcohols is the in situ formation of the corresponding esters via condensation of the carboxylic acids with the produced alcohols. Especially, the hydrogenation of polycarboxylic acids frequently suffers from the formation of a complex mixture of oligomeric esters. This issue was successfully overcome by the combined use of a dual catalyst that consists of a bulky (PNNP)iridium complex and a Lewis acid. Owing to the steric bulk and robustness of the iridium catalyst, the main role of the Lewis acid is to independently catalyze the esterification, albeit the cooperative activation of (a resting state of) the iridium catalyst by the Lewis acid also seems to be implied.

show abstract

Section: Introductionmentioning

confidence: 99%

Selective Reduction of Carboxylic Acids to Alcohols in the Presence of Alcohols by a Dual Bulky Transition-Metal Complex/Lewis Acid Catalyst

2022

View full text Add to dashboard Cite

show abstract

“…Integration of the β-oxidation degradation pathway with the ω-oxidation pathway offers an efficient strategy for generating high yields of MCFAs-derived compounds. Compared with previously reported MCDCAs biosynthetic pathways, such as the reverse β-oxidation pathway, ω-oxidation pathway, and LCFAs oxidation cleavage pathway, , this proof-of-principle route enjoys numerous advantages for producing the desired chemicals. Unlike glucose metabolism, FA catabolism generates directly the target products and acetyl-CoA for cell growth.…”

Section: Discussionmentioning

confidence: 99%

Reprogramming Escherichia coli Metabolism for Bioplastics Synthesis from Waste Cooking Oil

Cheng

Zhao

et al. 2021

ACS Synth. Biol.

View full text Add to dashboard Cite

The recycle and reutilization of food wastes is a promising alternative for supporting and facilitating circular economy. However, engineering industrially relevant model organisms to use food wastes as their sole carbon source has remained an outstanding challenge so far. Here, we reprogrammed Escherichia coli metabolism using modular pathway engineering followed by laboratory adaptive evolution to establish a strain that can efficiently utilize waste cooking oil (WCO) as the sole carbon source to produce monomers of bioplastics, namely, medium-chain α,ω-dicarboxylic acids (MCDCAs). First, the biosynthetic pathway of MCDCAs was designed and rewired by modifying the βoxidation pathway and introducing an ω-oxidation pathway. Then, metabolic engineering and laboratory adaptive evolution were applied for improving the pathway efficiency of fatty acids utilization. Finally, the engineered strain E. coli AA0306 was able to produce 15.26 g/L MCDCAs with WCO as the sole carbon source. This study provides an economically attractive strategy for biomanufacturing bioplastics from food wastes, which has a great potentiality to be developed as a wide range of enabling biotechnologies for achieving green revolution.

show abstract

“…Another promising candidate for improving the flexibility and toughness of PLA may be poly(butylene sebacate) (PBSe), a bio-based and biodegradable aliphatic polyester that can be synthesized by the polycondensation of sebacic acid (Se) with 1,4-butanediol (BDO) [ 43 ]. The bio-based character of PBSe comes from the fact that both of its precursor monomers can be obtained from renewable sources, Se being produced by the alkaline pyrolysis of castor oil [ 44 ] and BDO being obtainable via the microbial fermentation of sugars from renewable sources [ 45 ]. Similar to PLA, PBSe is a biodegradable polymer in composting conditions [ 46 ].…”

Section: Introductionmentioning

confidence: 99%

Bio-Based Poly(lactic acid)/Poly(butylene sebacate) Blends with Improved Toughness

et al. 2022

View full text Add to dashboard Cite

A series of poly(butylene sebacate) (PBSe) aliphatic polyesters weresuccessfully synthesized by the melt polycondensation of sebacic acid (Se) and 1,4-butanediol (BDO), two monomers manufactured on an industrial scale from biomass. The numberaverage molecular weight (Mn) in the range from 6116 to 10,779 g/mol and the glass transition temperature (Tg) of the PBSe polyesters were tuned by adjusting the feed ratio between the two monomers. Polylactic acid (PLA)/PBSe blends with PBSe concentrations between 2.5 to 20 wt% were obtained by melt compounding. For the first time, PBSe’s effect on the flexibility and toughness of PLA was studied. As shown by the torque and melt flow index (MFI) values, the addition of PBSe endowed PLA with both enhanced melt processability and flexibility. The tensile tests and thermogravimetric analysis showed that PLA/PBSe blends containing 20 wt% PBSe obtained using a BDO molar excess of 50% reached an increase in elongation at break from 2.9 to 108%, with a negligible decrease inYoung’s modulus from 2186 MPa to 1843 MPa, and slight decrease in thermal performances. These results demonstrated the plasticizing efficiency of the synthesized bio-derived polyesters in overcoming PLA’s brittleness. Moreover, the tunable properties of the resulting PBSe can be of great industrial interest in the context of circular bioeconomy.

show abstract

Microbial production of sebacic acid from a renewable source: production, purification, and polymerization

Abstract: Sebacic acid is an aliphatic ten-carbon dicarboxylic acid (1,10-decanedioic acid) with a variety of industrial applications. Here, we present its microbial production, purification, and polymerization.

Cited by 23 publications

References 28 publications

Selective Reduction of Carboxylic Acids to Alcohols in the Presence of Alcohols by a Dual Bulky Transition-Metal Complex/Lewis Acid Catalyst

Selective Reduction of Carboxylic Acids to Alcohols in the Presence of Alcohols by a Dual Bulky Transition-Metal Complex/Lewis Acid Catalyst

Reprogramming Escherichia coli Metabolism for Bioplastics Synthesis from Waste Cooking Oil

Bio-Based Poly(lactic acid)/Poly(butylene sebacate) Blends with Improved Toughness

Contact Info

Product

Resources

About