Steric Inhibition of Resonance in 1-Methyl-2-isopropenylbenzene

Murray, M. J.; Gallaway, W. S.

doi:10.1021/ja01191a098

Cited by 12 publications

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“…All samples were incubated at room temperature with the subsequent accumulation of styrene in the reaction mixture then followed at 247 nm for a total of 5 min at 20 s intervals using a UV/Vis spectrophotometer. A molar extinction coefficient of 10,000 M −1 cm −1 [50] and a 1 cm path length were used to establish activity in terms of mU mg −1 total protein. Total protein content in crude lysates was determined by Bradford Assay using bovine serum albumin (BSA) as an external standard.…”

Section: Methodsmentioning

confidence: 99%

Rational and combinatorial approaches to engineering styrene production by Saccharomyces cerevisiae

et al. 2014

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BackgroundStyrene is an important building-block petrochemical and monomer used to produce numerous plastics. Whereas styrene bioproduction by Escherichia coli was previously reported, the long-term potential of this approach will ultimately rely on the use of hosts with improved industrial phenotypes, such as the yeast Saccharomyces cerevisiae.ResultsClassical metabolic evolution was first applied to isolate a mutant capable of phenylalanine over-production to 357 mg/L. Transcription analysis revealed up-regulation of several phenylalanine biosynthesis pathway genes including ARO3, encoding the bottleneck enzyme DAHP synthase. To catalyze the first pathway step, phenylalanine ammonia lyase encoded by PAL2 from A. thaliana was constitutively expressed from a high copy plasmid. The final pathway step, phenylacrylate decarboxylase, was catalyzed by the native FDC1. Expression of FDC1 was naturally induced by trans-cinnamate, the pathway intermediate and its substrate, at levels sufficient for ensuring flux through the pathway. Deletion of ARO10 to eliminate the competing Ehrlich pathway and expression of a feedback-resistant DAHP synthase encoded by ARO4K229L preserved and promoted the endogenous availability precursor phenylalanine, leading to improved pathway flux and styrene production. These systematic improvements allowed styrene titers to ultimately reach 29 mg/L at a glucose yield of 1.44 mg/g, a 60% improvement over the initial strain.ConclusionsThe potential of S. cerevisiae as a host for renewable styrene production has been demonstrated. Significant strain improvements, however, will ultimately be needed to achieve economical production levels.Electronic supplementary materialThe online version of this article (doi:10.1186/s12934-014-0123-2) contains supplementary material, which is available to authorized users.

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Section: Methodsmentioning

confidence: 99%

Rational and combinatorial approaches to engineering styrene production by Saccharomyces cerevisiae

et al. 2014

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Zur Kenntnis der Sesquiterpene und Azulene. Mitteilung. Azulenaldehyde und Azulenketone: Bathochrome Verschiebungen durch sterische Hinderung der Resonanz

Heilbronner

Gerdil

1956

Helvetica Chimica Acta

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Die absolute Konfiguration von Carquejol und verwandten o‐Menthan‐Derivaten

Snatzke

Thomas

Ohloff

1969

Helvetica Chimica Acta

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The structure of carquejol is amended to that of cis‐3‐hydroxy‐o‐mentha‐1(7),4,8‐triene; the chirality has been confirmed as 2 R, 3 S by correlation with the (−)‐cis‐o‐menthane obtained from carquejol and that from (+)‐verbenene of known absolute configuration. The two double bonds of the dihydrocarquejol system (15 and 16) constitute a helical system, that especially in the case of the acetate (16) fixes the isopropenyl group in such a way that a very high Δϵ value in the CD. curve is observed. The conformational significance of this phenomenon is discussed.

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Steric Inhibition of Resonance in 1-Methyl-2-isopropenylbenzene

Cited by 12 publications

References 0 publications

Rational and combinatorial approaches to engineering styrene production by Saccharomyces cerevisiae

Rational and combinatorial approaches to engineering styrene production by Saccharomyces cerevisiae

Zur Kenntnis der Sesquiterpene und Azulene. Mitteilung. Azulenaldehyde und Azulenketone: Bathochrome Verschiebungen durch sterische Hinderung der Resonanz

Die absolute Konfiguration von Carquejol und verwandten o‐Menthan‐Derivaten

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