Cyclotetrasiloxane frameworks for the chemoenzymatic synthesis of oligoesters

Frampton, Mark B.; Jones, Timothy R. B.; Zelisko, Paul M.

doi:10.1039/c4ra14828b

Cited by 6 publications

(16 citation statements)

References 49 publications

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“…This new knowledge of how CalB interacted with siliconbased substrates made it possible to design as ynthesis of oligoesters based on ac yclotetrasiloxane framework ( Figure 20). [106] The larger cyclic siloxanem otif had as tronger influenceo nt he capacity of the enzyme to form oligomers and, as before,t here was ac orrelation between chain length and oligomerization. Short ester chain lengths, that is, those between five and seven carbon atoms, could barely be processed by CalB;e ven the ester with eight carbon atoms did not yield particularly hopefulr esults.…”

Section: Chain-length Selectivity By Calbmentioning

confidence: 52%

“…[91,106] While examiningt he enzymatic oligomerizationo ft he cyclic siloxanes, Framptone tal. [91] realizedt hat there was very little difference in substratec onversion if the chain lengths weres ufficiently long and, as such, hydrophobic.…”

Section: Chain-length Selectivity By Calbmentioning

confidence: 99%

“…These chain-length studies indicated that longerlinkages between reactive groups and the siloxane fragments would be an ecessary consideration when designing biocatalytic methodologieso fo rganosilanes. [91,106] While examiningt he enzymatic oligomerizationo ft he cyclic siloxanes, Framptone tal. [91] realizedt hat there was very little difference in substratec onversion if the chain lengths weres ufficiently long and, as such, hydrophobic.…”

Section: Chain-length Selectivity By Calbmentioning

confidence: 99%

“…By using MALDI-TOF MS, Frampton et al [106] were able to follow the growth of oligomers. Fractions were removed from the reactionm ixture, analyzed, and the individual chemical species were identified.…”

Section: Chain-length Selectivity By Calbmentioning

confidence: 99%

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Biocatalysis in Silicon Chemistry

Frampton

Zelisko

2017

Chemistry An Asian Journal

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The application of biocatalytic or chemoenzymatic techniquesi ns ilicon chemistry serves two roles:i tp rovides ag reater understanding of the processing of silicon species by natural systems, such as plants, diatoms, and sponges, as well openingu pa venues to green methodologies in the field. In the latter case, biocatalytic approaches have been applied to the synthesis of small-molecule systems and polymeric materials. Often these biocatalytic approaches allow access to molecular structures under mild conditions and, in some cases, molecular structures that are not accessible throught raditional chemical methodologies. Ar eview of recent advances in the applications of biocatalysis in silicon chemistry is presented.

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Section: Chain-length Selectivity By Calbmentioning

confidence: 52%

Section: Chain-length Selectivity By Calbmentioning

confidence: 99%

Section: Chain-length Selectivity By Calbmentioning

confidence: 99%

Section: Chain-length Selectivity By Calbmentioning

confidence: 99%

See 2 more Smart Citations

Biocatalysis in Silicon Chemistry

Frampton

Zelisko

2017

Chemistry An Asian Journal

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“…Perhaps using ionic liquids as a reaction media could solve this limitation. More recently, a cyclotetrasiloxane framework was used to synthesize oligoesters chemoenzymatically . This synthesis was characterized by an impressive consumption of monomers (65–80 %) in a relatively short time period (24–48 h).…”

Section: Recent Erop Techniques and Architectures Using Calbmentioning

confidence: 99%

Recent Developments and Optimization of Lipase-Catalyzed Lactone Formation and Ring-Opening Polymerization

Champagne

Strandman

Zhu

2016

Macromol. Rapid Commun.

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To obtain materials useful for the biomedical field, toxic catalysts should be removed from the synthetic route of polymerization reactions and of their precursors. Lipase-catalyzed ring-opening polymerization and the synthesis of cyclic precursors can be performed with the same catalyst under different conditions. Here, we highlight the use of lipases as catalysts and optimization of their performance for both ring-closing and ring-opening polymerization, via varying parameters such as ring size, concentration, substrate molar ratio, temperature, and solvent. While the conditions for ring-closing reactions and ring-opening polymerizations of small molecules, such as ε-caprolactone, have been extensively explored using Candida antarctica lipase B (CALB), the optimization of macrocyclization, especially for more bulky substrates is surveyed here. Finally, recent methods and polymer architectures are summarized with an emphasis on new procedures for more sustainable chemistry, such as the use of ionic liquids as solvents and recycling of polyesters by enzymatic pathways.

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