Stereoregularity in synthetic β-hydroxybutyrate and β-hydroxyvalerate homopolyesters

Bloembergen, Steven; Holden, David A.; Bluhm, Terry L.; Hamer, Gordon K.; Marchessault, R. H.

doi:10.1021/ma00194a027

Cited by 155 publications

(97 citation statements)

References 15 publications

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“…The amounts of polymer were expressed in terms of monomeric unit weight: 3-hydroxy butyric acid weight equivalent (HBA) for the PHB; HBA and 3-hydroxyvaleric acid (HVA) for the copolymer poly(3-hydroxybutyrateco-3-hydroxyvalerate) [P (HB-HV)] and HBA and 3-hydroxypropionic acid (HPA) for poly(3-hydroxybutyrate-co-3-hydroxypropionate) [P (HB-HP)]. The 13 C-NMR spectral analysis showed resonances that were consistent with data reported in literature for butyrate, valerate and propionate (Doi et al 1986;Bloemberg et al 1989). In particular, the signal resonances at d = 9.31 ppm and 19.72 ppm present in the 13 C-NMR spectrum of the copolyester were assigned to the carbon of the methyl valerate and butyrate group, respectively; the signal resonances at d = 67.62 ppm and d = 71.93 ppm were assigned to the carbon of the CHOH group belonging to the butyrate and valerate, respectively; the signal resonance at d = 26.76 ppm was assigned to the carbon of the methylene group adjacent to the methyl group belonging to the valerate; the signal resonances at d = 40.78 ppm and d = 38.78 ppm were assigned to the carbon of the methylene group adjacent to the carboxylic group of butyrate and valerate; respectively.…”

Section: Chemical and Physical Analyses For Data Collectionsupporting

confidence: 76%

Chemical-physical characterization of polyhydroxyalkanoates recovered by means of a simplified method from cultures of Halomonas campaniensis

Strazzullo

Gambacorta

Vella

et al. 2007

World J Microbiol Biotechnol

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In this study we suggest a simplified and effective method to directly recover polyhydroxyalkanoates (PHAs) from humid biomass of Halomonas campaniensis with no pre-treatment steps. Sodium dodecyl sulphate (SDS) was directly added to dispersed biomass of cultured micro-organism (w/w ratio: 1) in distilled water followed by shaking, heat treatment, and washing steps. The purity of the recovered PHAs synthesized by H. campaniensis was over 95%, regardless of the cell concentrations and the best yield was 12% (w/w) of the cell wet weight when the micro-organism was cultivated in a glucose-based medium or a glucose/propionate-based medium. MS spectroscopy and 1 H, 13 C-NMR analysis were used to chemically characterize the PHAs; their thermal characteristics were obtained using a differential scanning calorimeter and the average viscosity molecular weight was assessed through specific viscosity measurements. Due to its ease and velocity, our simplified method is suitable for the detection and recovery of PHAs from humid biomasses with high yield and purity. The method, which is quick and at low environmental impact, is very valuable for the simultaneous testing of cultures grown with different inducers for PHAs having particular chemical/physical characteristics.

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Section: Chemical and Physical Analyses For Data Collectionsupporting

confidence: 76%

Chemical-physical characterization of polyhydroxyalkanoates recovered by means of a simplified method from cultures of Halomonas campaniensis

Strazzullo

Gambacorta

Vella

et al. 2007

World J Microbiol Biotechnol

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“…[25][26][27] The carbonyl peak around 167 ppm is a particularly sensitive and effective signal, which provides the stereo information. [28][29][30] In case of observation of three peaks, the racemic polymer is present, indicating atactic fragments in the polymer chain corresponding to isotactic, syndiotactic, and heterotactic triads.…”

Section: -24mentioning

confidence: 99%

Synthesis and characterizations of new isotactic homopolyesters, statistical and block copolyesters derived of poly((S)‐3,3‐dimethylmalic acid) via the lactone route

Belibel

Azzouz

Barbaud

2015

J. Polym. Sci. Part A: Polym. Chem.

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This article presents the synthesis of a new family of synthetic isotactic polyesters derived from poly((S)‐3,3‐dimethylmalic acid) (PDMMLA). These polyesters are prepared via the lactone route bearing functionalized groups in its main or side chain. The aim of this work is twofold: metabolism and stereochemistry. First, the synthesis of these new polyesters is chosen to provide biodegradable polyesters biocompatible and bioassimilable by the human body. Next, the molecular chain of this family contains a stereogenic center in the aim to provide 100% isotactic homopolymers and copolymers (statistical and block). Finally, these polymers have been characterized by several analytical techniques: FTIR, 1H and 13C NMR, SEC, DSC, and TGA. The greatest importance will be given to the 13C NMR and DSC to principally confirm the stereoregularity and crystallinity of these stereopolyesters. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 1495–1507

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“…Atactic, syndiotactic, and isotactic PHBs have been reported. 108,109 The properties of naturally occurring PHAs depend on the composition: PHB is a highly crystalline, brittle polymer with T m = 177…”

Section: Poly(β-esters)mentioning

confidence: 99%

Polyesters

Fradet

Tessier

2003

Synthetic Methods in Step‐Growth Polymers

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Stereoregularity in synthetic β-hydroxybutyrate and β-hydroxyvalerate homopolyesters

Cited by 155 publications

References 15 publications

Chemical-physical characterization of polyhydroxyalkanoates recovered by means of a simplified method from cultures of Halomonas campaniensis

Chemical-physical characterization of polyhydroxyalkanoates recovered by means of a simplified method from cultures of Halomonas campaniensis

Synthesis and characterizations of new isotactic homopolyesters, statistical and block copolyesters derived of poly((S)‐3,3‐dimethylmalic acid) via the lactone route

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