Production of a chiral polyester by <i>Pseudomonas oleovorans</i> grown with 5‐phenyl‐2,4‐pentadienoic acid

Antoun, S.; Grizzi, Ilaria; Lenz, Robert W.; Fuller, R. C.

doi:10.1002/chir.530030615

Cited by 6 publications

(11 citation statements)

References 6 publications

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“…In numerous literature reports, the aromatic PHAs have been studied widely. Properties such as degradability (Olivera et al, 2001 ), surface structure (Takagi et al, 2004 ), solubility (Mizuno et al, 2017 ), and thermal behavior (Antoun et al, 1991 ) have been assessed, and their dependency on the polymer's structure was identified (Ishii-Hyakutake et al, 2018 ).…”

Section: Trends Unveiledmentioning

confidence: 99%

What Has Been Trending in the Research of Polyhydroxyalkanoates? A Systematic Review

Guzik

Witko

Steinbüchel

et al. 2020

Front. Bioeng. Biotechnol.

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Over the past decades, enormous progress has been achieved with regard to research on environmentally friendly polymers. One of the most prominent families of such biopolymers are bacterially synthesized polyhydroxyalkanoates (PHAs) that have been known since the 1920s. However, only as recent as the 1990s have extensive studies sprung out exponentially in this matter. Since then, different areas of exploration of these intriguing materials have been uncovered. However, no systematic review of undertaken efforts has been conducted so far. Therefore, we have performed an unbiased search of up-to-date literature to reveal trending topics in the research of PHAs over the past three decades by data mining of 2,227 publications. This allowed us to identify eight past and current trends in this area. Our study provides a comprehensive review of these trends and speculates where PHA research is heading.

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Section: Trends Unveiledmentioning

confidence: 99%

What Has Been Trending in the Research of Polyhydroxyalkanoates? A Systematic Review

Guzik

Witko

Steinbüchel

et al. 2020

Front. Bioeng. Biotechnol.

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“…Generally, to generate aromatic PHAs, defined compounds containing aromatic groups are added to the medium as a precursor (i.e., 5PhV or 5-phenyl-2,4-pentadienoic acid is used as a precursor to produce PHAs containing 3H5PhV [14,15,19,20]). However, there are a few reports on the production of aromatic PHAs without any supplementation with these defined aromatic compounds [16,18].…”

Section: Biosynthesized Phas Bearing Aromatic Groups As Side Chainsmentioning

confidence: 99%

“…The same polymer was obtained when P. putida BM01 [19] or P. putida KT2440 [15] was used as the PHA production host. It was reported that the P(3H5PhV) homopolymer was also produced from 5-phenyl-2,4-pentadienoic acid by P. oleovorans [20] and from 7PhV or 9PhN by P. putida U [25]. In the latter case, the 3H5PhV monomer would be generated through the β -oxidation cycle.…”

Section: Biosynthesized Phas Bearing Aromatic Groups As Side Chainsmentioning

confidence: 99%

“…However, the endothermic peak for the melting transition in the differential scanning calorimetry (DSC) thermogram was very small. This observation indicates that this polymer has a very low degree of crystallinity and is thus highly amorphous [20,27,52]. This is unusual because the homopolymer has a highly ordered isotactic structure, which generally provides an ordered packing structure in the solid state [21].…”

Section: Physical and Chemical Properties Of Aromatic Phasmentioning

confidence: 99%

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Biosynthesis and Characteristics of Aromatic Polyhydroxyalkanoates

2018

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Polyhydroxyalkanoates (PHAs) are polyesters synthesized by bacteria as a carbon and energy storage material. PHAs are characterized by thermoplasticity, biodegradability, and biocompatibility, and thus have attracted considerable attention for use in medical, agricultural, and marine applications. The properties of PHAs depend on the monomer composition and many types of PHA monomers have been reported. This review focuses on biosynthesized PHAs bearing aromatic groups as side chains. Aromatic PHAs show characteristics different from those of aliphatic PHAs. This review summarizes the types of aromatic PHAs and their characteristics, including their thermal and mechanical properties and degradation behavior. Furthermore, the effect of the introduction of an aromatic monomer on the glass transition temperature (Tg) of PHAs is discussed. The introduction of aromatic monomers into PHA chains is a promising method for improving the properties of PHAs, as the characteristics of aromatic PHAs differ from those of aliphatic PHAs.

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“…Several aromatic pendant groups with different functionalities, such as phenyl, phenoxy, methyphenyl, methylphenoxy, nitrophenyl, cyanophenoxy, fluorophenoxy, thiophenoxy, and benzoyl groups, have been incorporated into aromatic PHAs . However, only P(3H5PhV) ,− and poly(3-hydroxy-6-phenylhexanoate) have been biosynthesized as homopolymers, while all other aromatic PHAs have been incorporated as copolymers with P3HB or other aromatic groups.…”

Section: Introductionmentioning

confidence: 99%

Catalyzed Chemical Synthesis of Unnatural Aromatic Polyhydroxyalkanoate and Aromatic–Aliphatic PHAs with Record-High Glass-Transition and Decomposition Temperatures

Westlie

Chen

2020

Macromolecules

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The catalyzed chemical synthesis of polyhydroxyalkanoates (PHAs) via stereoselective ring-opening polymerization (ROP) of eight-membered cyclic diolides (8DLR, R denotes the two substituents on the ring) has shown its ability to synthesize a variety of stereoregular aliphatic PHAs, but its utility for the synthesis of aromatic PHAs has not yet been demonstrated. Here, we report that the controlled ROP of meso-8DLBn (Bn = benzyl)catalyzed by metal-based complexes supported by C2-Salen ligandsaffords syndiotactic ([rr] = 92%) poly(3-hydroxy-4-phenylbutyrate) (st-P3H4PhB) with a high molar mass (M n up to 147 kg mol–1) and the highest glass-transition temperature (43 °C) reported in the PHA family, whereas the ROP of rac-8DLBn leads to essentially pure isotactic ([mm] > 99%) it-P3H4PhB. With judicious selections of catalysts, monomers, and procedures, copolymerizations of meso-8DLBn with rac-8DLR (R = Me, n Bu) produces aromatic–aliphatic random, stereotapered, or crystalline stereo-diblock PHA copolymers. In particular, the copolymer of meso-8DLBn with rac-8DLBuP3H4PhB-co-P3HHp (M n = 205 kg mol–1)is a strong, hard, but ductile (∼191% elongation at break) material, displaying perhaps the highest decomposition temperature (281 °C) reported for PHAs to date.

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Production of a chiral polyester by Pseudomonas oleovorans grown with 5‐phenyl‐2,4‐pentadienoic acid

Cited by 6 publications

References 6 publications

What Has Been Trending in the Research of Polyhydroxyalkanoates? A Systematic Review

What Has Been Trending in the Research of Polyhydroxyalkanoates? A Systematic Review

Biosynthesis and Characteristics of Aromatic Polyhydroxyalkanoates

Catalyzed Chemical Synthesis of Unnatural Aromatic Polyhydroxyalkanoate and Aromatic–Aliphatic PHAs with Record-High Glass-Transition and Decomposition Temperatures

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