Synthesis and enantioselective enzymatic hydrolysis of rac-dimethylphenyl[1-phenylacetamido)ethyl]silane

Hengelsberg, Heidi; Tacke, Reinhold; Fritsche, Kirsten; Syldatk, Christoph; Wagner, Fritz

doi:10.1016/0022-328x(91)83279-d

Cited by 21 publications

(8 citation statements)

References 15 publications

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“…The enzymatic synthesis of (R)-(1-aminoethyl)dimethylphenylsilane from a racemic mixture of dimethylphenyl[1-(phenylacetamido)ethyl]silane using immobilized penicillin G acylase from E. coli has been demonstrated ( Fig. 11) [69]. The (R)-enantiomer was achieved in 40% yield and 92%ee (GLC) from DMSO, pH 7.5, at 37°C.…”

Section: Free Enzymes and Organosilicon Compoundsmentioning

confidence: 98%

“…10 The selective acylation of a silyl ether by Pseudomonas fluorescens lipase [66] Fig. 11 Synthetic scheme for the synthesis and resolution of (R)-(2-aminoethyl)dimethylphenylsilane by penicillin G acylase from E. coli [69] the N-carbamoyl trimethylsilylmethyl amino acid with either D-N-carbamoylase or L-N-carbamoylase afforded the desired enantiomers after 50% conversion (Fig. 13).…”

Section: Free Enzymes and Organosilicon Compoundsmentioning

confidence: 98%

See 1 more Smart Citation

Organosilicon Biotechnology

Frampton

Zelisko

2009

Silicon

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Inspired by Nature, biocatalysis and biotechnology have quickly become burgeoning fields in silicon chemistry. From cell cultures to isolated enzymes researchers are exploring the use of biological systems to affect chemical transformations at or near silicon atoms. This review will examine the history of biotechnology as it pertains to organosilicon compounds (i.e., compounds with one or more Si-C bonds) and provide some insights into future directions for the field.

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Section: Free Enzymes and Organosilicon Compoundsmentioning

confidence: 98%

Section: Free Enzymes and Organosilicon Compoundsmentioning

confidence: 98%

Organosilicon Biotechnology

Frampton

Zelisko

2009

Silicon

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“…The well-known penicillin G acylase enzyme was shown to selectively hydrolyze a specific phenylsilane from a racemic mixture. [180] An alcohol dehydrogenase from horse liver also displays the ability of oxidizing silylated alcohols. [181] Besides natural biocatalysts, enzyme engineering expanded the scope of enzymatic functionalization of organosilanes.…”

Section: Enzymatic Synthesis Of Organosilicon Compoundsmentioning

confidence: 99%

Intersecting Xenobiology and Neometabolism To Bring Novel Chemistries to Life

Nieto-Domínguez

Nikel

2020

ChemBioChem

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The diversity of life relies on a handful of chemical elements (carbon, oxygen, hydrogen, nitrogen, sulfur and phosphorus) as part of essential building blocks; some other atoms are needed to a lesser extent, but most of the remaining elements are excluded from biology. This circumstance limits the scope of biochemical reactions in extant metabolism – yet it offers a phenomenal playground for synthetic biology. Xenobiology aims to bring novel bricks to life that could be exploited for (xeno)metabolite synthesis. In particular, the assembly of novel pathways engineered to handle nonbiological elements (neometabolism) will broaden chemical space beyond the reach of natural evolution. In this review, xeno‐elements that could be blended into nature's biosynthetic portfolio are discussed together with their physicochemical properties and tools and strategies to incorporate them into biochemistry. We argue that current bioproduction methods can be revolutionized by bridging xenobiology and neometabolism for the synthesis of new‐to‐nature molecules, such as organohalides.

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“…[8][9][10][11][12][13][14] This work has been the subject of otherr eviewsa nd as such is only briefly discussed herein.…”

Section: Inspired By Naturementioning

confidence: 99%

“…The use of isolated enzymes to affect biotransformations in organosilicon chemistry has been known since work by the Tacke group in the 1980s and 1990s . This work has been the subject of other reviews and as such is only briefly discussed herein.…”

Section: Inspired By Naturementioning

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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Synthesis and enantioselective enzymatic hydrolysis of rac-dimethylphenyl[1-phenylacetamido)ethyl]silane

Cited by 21 publications

References 15 publications

Organosilicon Biotechnology

Organosilicon Biotechnology

Intersecting Xenobiology and Neometabolism To Bring Novel Chemistries to Life

Biocatalysis in Silicon Chemistry

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