Organosilicon Biotechnology

Frampton, Mark B.; Zelisko, Paul M.

doi:10.1007/s12633-009-9021-3

Cited by 36 publications

(37 citation statements)

References 104 publications

(180 reference statements)

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“…Silicon constitutes almost 30% of the mass of the Earth’s crust, yet no life form is known to have the ability to forge carbon–silicon bonds (1). Despite the absence of organosilicon compounds in the biological world, synthetic chemistry has enabled us to appreciate the unique and desirable properties that have led to their broad applications in chemistry and material science (2, 3).…”

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confidence: 99%

Directed evolution of cytochrome c for carbon–silicon bond formation: Bringing silicon to life

Kan

Lewis

Chen

et al. 2016

Science

510

406

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Enzymes that catalyze carbon–silicon bond formation are unknown in nature, despite the natural abundance of both elements. Such enzymes would expand the catalytic repertoire of biology, enabling living systems to access chemical space previously only open to synthetic chemistry. We have discovered that heme proteins catalyze the formation of organosilicon compounds under physiological conditions via carbene insertion into silicon–hydrogen bonds. The reaction proceeds both in vitro and in vivo, accommodating a broad range of substrates with high chemo- and enantioselectivity. Using directed evolution, we enhanced the catalytic function of cytochrome c from Rhodothermus marinus to achieve more than 15-fold higher turnover than state-of-the-art synthetic catalysts. This carbon–silicon bond-forming biocatalyst offers an environmentally friendly and highly efficient route to producing enantiopure organosilicon molecules.

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confidence: 99%

Directed evolution of cytochrome c for carbon–silicon bond formation: Bringing silicon to life

Kan

Lewis

Chen

et al. 2016

Science

510

406

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“…In the experiment, sodium methylsiliconate resin was not found to be utilized by diatoms when it was the sole source of silicon. Since that time, studies of hydrolysis of organosilicate esters have differentiated active sites of serine proteases [19] as well as the biologically mediated transformation of organosilicon compounds [20]. Despite the ability of a variety of enzymatic and non-enzymatic proteins to interact with organosilicates, the in vivo conversion of organosilicates to higher order structures containing organic substitution has not been observed.…”

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confidence: 99%

Hydroxymethylsilanetriol – A Simple Analog of Silicic Acid

Arkles

King

Pannell

2013

Silicon

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Hydroxymethyltriethoxysilane and hydroxymethyltrimethoxysilane, precursors by hydrolysis to a simple analog of silicic acid, hydroxymethylsilanetriol, were prepared. Hydroxymethyltrialkoxysilanes undergo condensation to form silmethyleneoxide oligomers and dimeric 2,2,5,5-tetraalkoxy-2,5-disila-1,4-dioxanes. Hydroxymethylsilanetriol undergoes condensation reactions similar to silicic acid and readily forms organosilicate structures by sol-gel processing techniques which may be converted at relatively low temperatures to silicon dioxide. Hydroxmethylsilanetriol derived gels were subject to less stresscracking during drying than conventional tetraethoxysilane derived gels, suggesting that Si-O-C bond equilibration during drying provides a mechanism for stress-relief. In screening experiments, hydroxymethylsilanetriol appears to be a competitive inhibitor of the growth of the diatom C. fusiformis, a silicate dependent species, which produces silicate structures.

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“…[9,13,15,16] These transformations were accomplished both with whole microorganisms and free enzymes. This work has been reviewed in greater detail previously, [17] and the reader is referred to this paper forf urther details about these biocatalytic reactions.…”

Section: Inspired By Naturementioning

confidence: 99%

“…An example of early research into silicon biocatalysis. [17] Figure 2. Silica spicules from the sponge T. aurantia (A) and the silicatein filaments that template and catalyze the condensation of Si(OH) 4 in vivo (B).…”

Section: Silicateinmentioning

confidence: 99%

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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Organosilicon Biotechnology

Cited by 36 publications

References 104 publications

Directed evolution of cytochrome c for carbon–silicon bond formation: Bringing silicon to life

Directed evolution of cytochrome c for carbon–silicon bond formation: Bringing silicon to life

Hydroxymethylsilanetriol – A Simple Analog of Silicic Acid

Biocatalysis in Silicon Chemistry

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