Efficient production of 2-pyrone 4,6-dicarboxylic acid as a novel polymer-based material from protocatechuate by microbial function

Abstract

Sphingomonas paucimobilis SYK-6, which can degrade various low molecular weight compounds derived from plant polyphenols such as lignin, lignan, and tannin, metabolizes these substances via 2-pyrone-4,6-dicarboxylic acid (PDC). We focused on this metabolic intermediate as a potential raw material for novel, bio-based polymers. We cloned the ligAB and ligC genes of SYK-6, which respectively encode protocatechuate 4,5-dioxygenase and 4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase, into a broad host range plasmid vector, pKT230MC. The resulting plasmid, pDVABC, was introduced into the PpY1100 strain of Pseudomonas putida, and we found that PDC could be stably produced from protocatechuate and accumulated. In addition, we examined the efficiency of production of PDC from protocatechuate on a 5-L scale in a Luria-Bertani medium containing 100 mM glucose and determined that PDC was stably produced from protocatechuate to yield 10 g/L or more.

Tenacious Epoxy Adhesives Prepared from Lignin-derived Stable Metabolic Intermediate

“…PDC was prepared from protocatechuate via the metabolic pathway of Sphingomonas paucimobilis SYK-6 as reported previously [14].…”

“…Although lignin is the typical waste biomass, its chemical application has been limited [4] because of difficulties in transforming its highly networked structure. Recently, we reported the massive production of 2-pyrone-4,6-dicarboxylic acid (PDC) from lignin via protocatechuate by the action of transformed bacterium [14]. PDC is produced in the major metabolic pathway of biodegradation of aromatic substances [15] and it consists of the polar pseudo-aromatic ring system and two carboxylic acids (Fig.…”

Click synthesis and adhesive properties of novel biomass-based polymers from lignin-derived stable metabolic intermediate

“…In a previous study, we succeeded in the metabolic conversion of lignin into 2-pyrone-4,6-dicarboxylic acid (PDC) on a large scale via protocatechuate by a transformed bacterium. 6 PDC consists of a polar pseudo-aromatic ring and two carboxylic acids, suggesting the potential use as a bifunctional monomer for polycondensation and polyaddition. As PDC was not accessible from petrochemicals, its chemical reactivity and physical properties were comprehensively investigated.…”

Subcritical Water Extraction of Low-molecular-weight Phenolic Compounds from Oil Palm Biomass

“…1) can be prepared using C 6 -C 1 or C 6 -C 3 low-molecular-weight phenolic compounds (e.g. p-hydroxybenzoic acid, protocatechualdehyde, syringaldehyde, vanillin, p-coumaric acid and ferulic acid; hereinafter referred to as "PDC precursors") by fermentation using transgenic bacteria (Otsuka et al 2006), and PDC can easily be converted into various useful polymers such as polyester, polyurethane, and polyamide. The conventional method used to prepare these PDC precursors is the alkaline nitrobenzene oxidation decomposition of lignin (Otsuka et al 2006, Xiang & Lee 2001.…”