Selective pyrone functionalization: reductive alkylation of triacetic acid lactone

Kraus, George A.; Basemann, Kevin; Guney, Tezcan

doi:10.1016/j.tetlet.2015.01.141

Cited by 15 publications

(15 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Here, we focus on the interesting, yet simple, polyketide, triacetic acid lactone (TAL) as it is derived from two common polyketide precursors, acetyl-CoA and malonyl-CoA. TAL has been demonstrated as a platform chemical that can be converted into a variety of valuable products traditionally derived from fossil fuels including sorbic acid, a common food preservative with a global demand of 100,000 t (1,(15)(16)(17)(18). However, meeting this annual demand using the low concentrations of TAL derived from native plants like gerbera daisies (9) would require four times the quantity of global arable land.…”

mentioning

confidence: 99%

Rewiring Yarrowia lipolytica toward triacetic acid lactone for materials generation

Markham

Palmer

Chwatko

et al. 2018

Proc. Natl. Acad. Sci. U.S.A.

152

151

View full text Add to dashboard Cite

Polyketides represent an extremely diverse class of secondary metabolites often explored for their bioactive traits. These molecules are also attractive building blocks for chemical catalysis and polymerization. However, the use of polyketides in larger scale chemistry applications is stymied by limited titers and yields from both microbial and chemical production. Here, we demonstrate that an oleaginous organism (specifically, ) can overcome such production limitations owing to a natural propensity for high flux through acetyl-CoA. By exploring three distinct metabolic engineering strategies for acetyl-CoA precursor formation, we demonstrate that a previously uncharacterized pyruvate bypass pathway supports increased production of the polyketide triacetic acid lactone (TAL). Ultimately, we establish a strain capable of producing over 35% of the theoretical conversion yield to TAL in an unoptimized tube culture. This strain also obtained an averaged maximum titer of 35.9 ± 3.9 g/L with an achieved maximum specific productivity of 0.21 ± 0.03 g/L/h in bioreactor fermentation. Additionally, we illustrate that a β-oxidation-related overexpression () can support high TAL production and is capable of achieving over 43% of the theoretical conversion yield under nitrogen starvation in a test tube. Next, through use of this bioproduct, we demonstrate the utility of polyketides like TAL to modify commodity materials such as poly(epichlorohydrin), resulting in an increased molecular weight and shift in glass transition temperature. Collectively, these findings establish an engineering strategy enabling unprecedented production from a type III polyketide synthase as well as establish a route through O-functionalization for converting polyketides into new materials.

show abstract

mentioning

confidence: 99%

Rewiring Yarrowia lipolytica toward triacetic acid lactone for materials generation

Markham

Palmer

Chwatko

et al. 2018

Proc. Natl. Acad. Sci. U.S.A.

152

151

View full text Add to dashboard Cite

show abstract

“…Diversification at C3 and C6 was targeted, along with some modification of the pyrone core (Scheme ). , We then investigated the impact of these analogues on biofilm and swarming properties in B. atropheaus.…”

Section: Resultsmentioning

confidence: 99%

Pyrones Identified as LuxR Signal Molecules in Photorhabdus and Their Synthetic Analogues Can Alter Multicellular Phenotypic Behavior of Bacillus atropheaus

et al. 2021

View full text Add to dashboard Cite

Individual bacteria communicate by the release and interpretation of small molecules, a phenomenon known as quorum sensing (QS). We hypothesized that QS compounds extruded by Photorhabdus could be interpreted by Bacillusa form of interspecies communication. We interrogate the structure−activity relationship within the recently discovered pyrone QS network and reveal the exquisite structural features required for targeted phenotypic behavior. The interruption of QS is an exciting, nonbiocidal approach to tackling infection, and understanding its nuances can only be achieved by studies such as this.

show abstract

“…Also, Crypton and Hydroquinone are best known to have potential antifungal and antibacterial activities [35,36]. Furthermore, long-chain unsaturated fatty acids (LCUFAs), such as triacetic acid lactone, also show higher antibacterial activity and are considered to be the essential ingredients of antimicrobial, food additives and some antibacterial activities [37]. Moreover, Calder [38] has reported a similar investigation as an anti-inflammatory agent for these compounds.…”

Section: IIImentioning

confidence: 99%

Active Fractions of Methanol Crude Obtained from Acacia Seyal Gum and their Antiproliferative Effects against Human Breast Cancer Cell Lines

Elnour¹,

Mirghani²,

Kabbashi³

et al. 2020

GJSFR

View full text Add to dashboard Cite

Background: This study is on Acacia seyal gum, which is an exudate from Talha (Acacia seyal) tree. It provides a rich source of prebiotic that is used traditionally in folk medicine. Aims: The anti-proliferative effect (APE) of Acacia seyal gum (ASG) and Prebio-T-commercial (PTC) samples on human breast cancer (MCF-7) cell lines, and their antioxidant activities (AA) were investigated. Methods: The methanol crude extracts of both Acacia seyal gum and Prebio-T- commercial were fractioned into acetone and methanol, respectively. The anti-proliferative effect on human breast cancer cell lines for each fraction was examined using sulphorhodamine assay (SRB assay). Methanol crude extracts and their active compositions were analysed carefully using Gas chromatography-mass spectrometry technique.

show abstract

Selective pyrone functionalization: reductive alkylation of triacetic acid lactone

Abstract: a b s t r a c tThe one-pot reaction of aldehydes, triacetic acid lactone, and Hantzsch 1,4-dihydropyridine affords 3-alkyl pyrones via a reductive alkylation strategy.

Cited by 15 publications

References 11 publications

Rewiring Yarrowia lipolytica toward triacetic acid lactone for materials generation

Rewiring Yarrowia lipolytica toward triacetic acid lactone for materials generation

Pyrones Identified as LuxR Signal Molecules in Photorhabdus and Their Synthetic Analogues Can Alter Multicellular Phenotypic Behavior of Bacillus atropheaus

Active Fractions of Methanol Crude Obtained from Acacia Seyal Gum and their Antiproliferative Effects against Human Breast Cancer Cell Lines

Contact Info

Product

Resources

About