The heterogeneous selective reduction of PHB as a useful method for preparation of oligodiols and surface modification

Chaber, Paweł; Kwiecień, Michał; Zięba, Magdalena; Sobota, Michał; Adamus, Grażyna

doi:10.1039/c7ra06111k

Cited by 14 publications

(12 citation statements)

References 34 publications

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“…The structural characterization of the oligomers conducted using NMR and ESI-MS n analyses confirmed that oligomers were terminated by two hydroxyl end groups. The reduction of the PHA occurred in a statistical way, regardless of the chemical structure of the comonomer units or of the microstructure of the polyester chain [71,72]. This method can be used to synthesize various PHA oligodiols that were useful in the further synthesis of tailor-made biodegradable materials [73,74].…”

Section: Functionalization Of Pha To Oligomers Containing Hydroxyl End Groupsmentioning

confidence: 99%

Bioactive and Functional Oligomers Derived from Natural PHA and Their Synthetic Analogs

Ekere¹,

Kurcok²,

Adamus³

et al. 2020

The Handbook of Polyhydroxyalkanoates

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Section: Functionalization Of Pha To Oligomers Containing Hydroxyl End Groupsmentioning

confidence: 99%

Bioactive and Functional Oligomers Derived from Natural PHA and Their Synthetic Analogs

Ekere¹,

Kurcok²,

Adamus³

et al. 2020

The Handbook of Polyhydroxyalkanoates

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“…The observed decrease in the PHA’s M w impairs the utilization of the biopolymer in most of the conventional applications of plastics due to the loss of mechanical properties. Nevertheless, there are specific applications for which low-M w PHAs are of interest, such as their utilization as plasticizers [ 44 ] and surfactants, or for the preparation of graft and block co-polymers, which are useful for the fabrication of bio-adhesives, drug-delivery systems, drug-coating systems, and tissue-engineering materials [ 45 , 46 , 47 ]. Nevertheless, for biomedical and pharmaceutical uses, the biopolymers would require further purification to meet the requirements of such high-value areas.…”

Section: Resultsmentioning

confidence: 99%

“…Nevertheless, for biomedical and pharmaceutical uses, the biopolymers would require further purification to meet the requirements of such high-value areas. For such applications, the PHA molecules are depolymerized into monomers or short oligomers (10 2 –10 4 g/mol) by physical (e.g., thermal decomposition), chemical methods (e.g., acid hydrolysis, alcoholysis), and/or enzymatic methods [ 46 , 47 , 48 ]. The developed SBW–hypochlorite digestion methodology could be of great value for the extraction of the biopolymer with the appropriate M w for use in such areas of application, without the need to resort to the chemical hydrolysis of high-M w PHA.…”

Section: Resultsmentioning

confidence: 99%

Subcritical Water as a Pre-Treatment of Mixed Microbial Biomass for the Extraction of Polyhydroxyalkanoates

et al. 2022

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Polyhydroxyalkanoate (PHA) recovery from microbial cells relies on either solvent extraction (usually using halogenated solvents) and/or digestion of the non-PHA cell mass (NPCM) by the action of chemicals (e.g., hypochlorite) that raise environmental and health hazards. A greener alternative for PHA recovery, subcritical water (SBW), was evaluated as a method for the dissolution of the NPCM of a mixed microbial culture (MMC) biomass. A temperature of 150 °C was found as a compromise to reach NPCM solubilization while mostly preventing the degradation of the biopolymer during the procedure. Such conditions yielded a polymer with a purity of 77%. PHA purity was further improved by combining the SBW treatment with hypochlorite digestion, in which a significantly lower hypochlorite concentration (0.1%, v/v) was sufficient to achieve an overall polymer purity of 80%. During the procedure, the biopolymer suffered some depolymerization, as evidenced by the lower molecular weight (Mw) and higher polydispersity of the extracted samples. Although such changes in the biopolymer’s molecular mass distribution impact its mechanical properties, impairing its utilization in most conventional plastic uses, the obtained PHA can find use in several applications, for example as additives or for the preparation of graft or block co-polymers, in which low-Mw oligomers are sought.

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“…The higher density of these groups was attained by using lithium borohydride (LiBH 4 ). In our previous study, this reducing agent permitted us to obtain low-molar-mass poly(3-hydroxybutyrate) (PHB) with hydroxyl terminal groups, which was confirmed by GPC, proton NMR, and ESI-MS experiments [ 53 ]. The oligomers, of course, were synthesized in a heterogeneous system, that is, by reducing high-molar-mass PHB in the form of a powder.…”

Section: Introductionmentioning

confidence: 95%

Surface Modification of PHBV Fibrous Scaffold via Lithium Borohydride Reduction

et al. 2022

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In this study, lithium borohydride (LiBH4) reduction was used to modify the surface chemistry of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBV) fibers. Although the most common reaction employed in the surface treatment of polyester materials is hydrolysis, it is not suitable for fiber modification of bacterial polyesters, which are highly resistant to this type of reaction. The use of LiBH4 allowed the formation of surface hydroxyl groups under very mild conditions, which was crucial for maintaining the fibers’ integrity. The presence of these groups resulted in a noticeable improvement in the surface hydrophilicity of PHBV, as revealed by contact angle measurements. After the treatment with a LiBH4 solution, the electrospun PHBV fibrous mat had a significantly greater number of viable osteoblast-like cells (SaOS-2 cell line) than the untreated mat. Moreover, the results of the cell proliferation measurements correlated well with the observed cell morphology. The most flattened SaOS-2 cells were found on the surface that supported the best cell attachment. Most importantly, the results of our study indicated that the degree of surface modification could be controlled by changing the degradation time and concentration of the borohydride solution. This was of great importance since it allowed optimization of the surface properties to achieve the highest cell-proliferation capacity.

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The heterogeneous selective reduction of PHB as a useful method for preparation of oligodiols and surface modification

Abstract: A selective heterogeneous reduction of natural PHB with lithium borohydride as a reducing agent has been described.

Cited by 14 publications

References 34 publications

Bioactive and Functional Oligomers Derived from Natural PHA and Their Synthetic Analogs

Bioactive and Functional Oligomers Derived from Natural PHA and Their Synthetic Analogs

Subcritical Water as a Pre-Treatment of Mixed Microbial Biomass for the Extraction of Polyhydroxyalkanoates

Surface Modification of PHBV Fibrous Scaffold via Lithium Borohydride Reduction

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