Heterostereocomplex‐ and Homocrystallization and Thermal Properties and Degradation of Substituted Poly(lactic acid)s, Poly(<scp>l</scp>‐2‐hydroxybutanoic acid) and Poly(<scp>d</scp>‐2‐hydroxy‐3‐methylbutanoic acid)

Tsuji, Hideto; Hayakawa, Tomohiro

doi:10.1002/macp.201600359

Cited by 11 publications

(10 citation statements)

References 103 publications

(186 reference statements)

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“…For solvent evaporated 50/50/0 blend, the melting peaks of L-P2HB and D-PLA homo-crystallites and D-PLA/L-P2HB HTSC crystallites appeared at 102, 163, and 168 °C, respectively. The melting temperature ( T m ) values of L-P2HB/D-P2H3MB HTSC crystallites and D-PLA/L-P2HB HTSC values are consistent with the reported values71727374.…”

Section: Resultssupporting

confidence: 90%

“…These results are indicative of the fact that ternary stereocomplex crystallites contain a higher amount of larger sized d -configured D-P2H3MB and a lower amount of small sized d -configured D-PLA and the attractive force of l -configured L-P2HB during precipitation and solvent evaporation acted correspondingly slightly and much stronger for d -configured D-P2H3MB than for d -configured D-PLA. These results are consistent with the fact that HTSC formation occurs readily between L-P2HB and D-P2H3MB compared to that between D-PLA and L-P2HB71727374.…”

Section: Discussionsupporting

confidence: 90%

“…The shown ratios in the figure are those of D-PLA/L-P2HB/D-P2H3MB (mol/mol/mol). For precipitated 0/50/50 blend, i.e., precipitated L-P2HB/D-P2H3MB 50/50 blend, L-P2HB/D-P2H3MB HTSC crystalline peaks were observed at 10.2, 17.7, 18.5, and 20.4° 7374 and D-P2H3MB and L-P2HB homo-crystalline peaks were seen at 13.8 and 14.9°, respectively22. For solvent evaporated 0/50/50 blend, in addition to L-P2HB/D-P2H3MB HTSC crystalline peaks which appeared at the 2θ values similar to those of precipitated 0/50/50 blend, D-P2H3MB homo-crystalline peaks appeared at 12.9 and 14.0°22 and no L-P2HB homo-crystalline peak was observed.…”

Section: Resultsmentioning

confidence: 99%

“…On the other hand, SC between the polymers with different chemical structures and opposite configurations, i.e., hetero-stereocomplexes (HTSCs) are formed between two oppositely configured polyesters: PLA and P2HB7172, P2HB and P2H3MB7374, oppositely configured polyester and polypeptides: d -configured D-PLA and l -configured polypeptides75767778798081828384, and oppositely configured polyketones: poly(propylene- alt -carbon monoxide) and poly(1-butene- alt -carbon monoxide)32. Ternary stereocomplex formation takes place in three optically active polyesters: enantiomeric P2HBs and either L-PLA or D-PLA, wherein the polymers with two different chemical structures are contained8586.…”

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confidence: 99%

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Configurational Molecular Glue: One Optically Active Polymer Attracts Two Oppositely Configured Optically Active Polymers

Tsuji

Noda

Kimura

et al. 2017

Sci Rep

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D-configured poly(D-lactic acid) (D-PLA) and poly(D-2-hydroxy-3-methylbutanoic acid) (D-P2H3MB) crystallized separately into their homo-crystallites when crystallized by precipitation or solvent evaporation, whereas incorporation of L-configured poly(L-2-hydroxybutanoic acid) (L-P2HB) in D-configured D-PLA and D-P2H3MB induced co-crystallization or ternary stereocomplex formation between D-configured D-PLA and D-P2H3MB and L-configured L-P2HB. However, incorporation of D-configured poly(D-2-hydroxybutanoic acid) (D-P2HB) in D-configured D-PLA and D-P2H3MB did not cause co-crystallization between D-configured D-PLA and D-P2H3MB and D-configured D-P2HB but separate crystallization of each polymer occurred. These findings strongly suggest that an optically active polymer (L-configured or D-configured polymer) like unsubstituted or substituted optically active poly(lactic acid)s can act as “a configurational or helical molecular glue” for two oppositely configured optically active polymers (two D-configured polymers or two L-configured polymers) to allow their co-crystallization. The increased degree of freedom in polymer combination is expected to assist to pave the way for designing polymeric composites having a wide variety of physical properties, biodegradation rate and behavior in the case of biodegradable polymers.

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Section: Resultssupporting

confidence: 90%

Section: Discussionsupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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Configurational Molecular Glue: One Optically Active Polymer Attracts Two Oppositely Configured Optically Active Polymers

Tsuji

Noda

Kimura

et al. 2017

Sci Rep

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“…411 Heterostereocomplexes of PHBs and PLLA were recently investigated and such complexes feature enhanced thermal properties. [412][413][414][415] As it stands, there exists a massive library of potential heterostereocomplexes and other interesting materials will certainly be discovered. These developments in stereocomplexation are expected to place stereochemistry at the forefront of renewable polymer advancement.…”

Section: Pla and Other Degradable Polymersmentioning

confidence: 99%

Stereochemical enhancement of polymer properties

et al. 2019

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The importance of stereochemistry to the function of molecules is generally well understood. However, to date, control over stereochemistry and its potential to influence properties of the resulting polymers are, as yet, not fully realised. This review focuses on the state-of-the-art with respect to how stereochemistry in polymers has been used to influence and control their physical and mechanical properties as well as begin to control their function. A brief overview of the synthetic methodology by which to access these materials is included, with the main focus directed towards stereochemical control over properties such as mechanical, biodegradation and conductivity. Additionally, the advances being made towards enantioseparation, enantioselective catalyst supports and stereo-directed transitions are discussed. Finally, we also consider the opportunities that the rich stereochemistry of sustainably-sourced monomers could offer in this field. Where possible, parallels and general design principles are drawn together to identify opportunities and limitations that these approaches may present in their effects on materials properties, performance and function.

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A synthetic pathway for the production of 2-hydroxyisovaleric acid in Escherichia coli

Cheong

Clomburg

González

2018

Journal of Industrial Microbiology and Biotechnology

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Synthetic biology, encompassing the design and construction of novel artificial biological pathways and organisms and the redesign of existing natural biological systems, is rapidly expanding the number of applications for which biological systems can play an integral role. In the context of chemical production, the combination of synthetic biology and metabolic engineering approaches continues to unlock the ability to biologically produce novel and complex molecules from a variety of feedstocks. Here, we utilize a synthetic approach to design and build a pathway to produce 2-hydroxyisovaleric acid in Escherichia coli and demonstrate how pathway design can be supplemented with metabolic engineering approaches to improve pathway performance from various carbon sources. Drawing inspiration from the native pathway for the synthesis of the 5-carbon amino acid L-valine, we exploit the decarboxylative condensation of two molecules of pyruvate, with subsequent reduction and dehydration reactions enabling the synthesis of 2-hydroxyisovaleric acid. Key to our approach was the utilization of an acetolactate synthase which minimized kinetic and regulatory constraints to ensure sufficient flux entering the pathway. Critical host modifications enabling maximum product synthesis from either glycerol or glucose were then examined, with the varying degree of reduction of these carbons sources playing a major role in the required host background. Through these engineering efforts, the designed pathway produced 6.2 g/L 2-hydroxyisovaleric acid from glycerol at 58% of maximum theoretical yield and 7.8 g/L 2-hydroxyisovaleric acid from glucose at 73% of maximum theoretical yield. These results demonstrate how the combination of synthetic biology and metabolic engineering approaches can facilitate bio-based chemical production.

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Heterostereocomplex‐ and Homocrystallization and Thermal Properties and Degradation of Substituted Poly(lactic acid)s, Poly(l‐2‐hydroxybutanoic acid) and Poly(d‐2‐hydroxy‐3‐methylbutanoic acid)

Cited by 11 publications

References 103 publications

Configurational Molecular Glue: One Optically Active Polymer Attracts Two Oppositely Configured Optically Active Polymers

Configurational Molecular Glue: One Optically Active Polymer Attracts Two Oppositely Configured Optically Active Polymers

Stereochemical enhancement of polymer properties

A synthetic pathway for the production of 2-hydroxyisovaleric acid in Escherichia coli

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