Combined Biocatalytic and Chemical Transformations of Oleic Acid to ω-Hydroxynonanoic Acid and α,ω-Nonanedioic Acid

2016 ◽  
Vol 358 (19) ◽  
pp. 3084-3092 ◽  
Author(s):  
Satish Koppireddi ◽  
Joo-Hyun Seo ◽  
Eun-Yeong Jeon ◽  
Partha Sarathi Chowdhury ◽  
Hyun-Young Jang ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Chemical Transformations ◽  
Nonanedioic Acid

scholarly journals Multi-Step Enzymatic Synthesis of 1,9-Nonanedioic Acid from a Renewable Fatty Acid and Its Application for the Enzymatic Production of Biopolyesters

Polymers ◽  
2019 ◽  
Vol 11 (10) ◽  
pp. 1690
Author(s):  
Lee ◽  
Kang ◽  
Kim ◽  
Seo ◽  
Pyo ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Immobilized Lipase ◽  
Diphenyl Ether ◽  
Average Molecular Weight ◽  
Reaction Medium ◽  
Building Blocks ◽  
Biological Synthesis ◽  
Enzymatic Production ◽  
Nonanedioic Acid ◽  
Long Chain

1,9-Nonanedioic acid is one of the valuable building blocks for producing polyesters and polyamides. Thereby, whole-cell biosynthesis of 1,9-nonanedioic acid from oleic acid has been investigated. A recombinant Corynebacterium glutamicum, expressing the alcohol/aldehyde dehydrogenases (ChnDE) of Acinetobacter sp. NCIMB 9871, was constructed and used for the production of 1,9-nonanedioic acid from 9-hydroxynonanoic acid, which had been produced from oleic acid. When 9-hydroxynonanoic acid was added to a concentration of 20 mM in the reaction medium, 1,9-nonanedioic acid was produced to 16 mM within 8 h by the recombinant C. glutamicum. The dicarboxylic acid was isolated via crystallization and then used for the production of biopolyester by a lipase. For instance, the polyesterification of 1,9-nonanedioic acid and 1,8-octanediol in diphenyl ether by the immobilized lipase B from Candida antarctica led to formation of the polymer product with the number-average molecular weight (Mn) of approximately 21,000. Thereby, this study will contribute to biological synthesis of long chain dicarboxylic acids and their application for the enzymatic production of long chain biopolyesters.

A magnetic super lattice

1987 ◽  
Vol 45 ◽  
pp. 360-361 ◽  
Author(s):  
M.D. Bentzon ◽  
J. v. Wonterghem ◽  
A. Thölén
Keyword(s):  
Thermal Decomposition ◽  
Oleic Acid ◽  
Magnetic Fluid ◽  
Magnetic Particles ◽  
Carbon Film ◽  
Thick Layer ◽  
Amorphous Iron ◽  
Super Lattice ◽  
Carrier Liquid ◽  
Median Diameter

We report on the oxidation of a magnetic fluid. The oxidation results in magnetic super lattice crystals. The “atoms” are hematite (α-Fe2O3) particles with a diameter ø = 6.9 nm and they are covered with a 1-2 nm thick layer of surfactant molecules.Magnetic fluids are homogeneous suspensions of small magnetic particles in a carrier liquid. To prevent agglomeration, the particles are coated with surfactant molecules. The magnetic fluid studied in this work was produced by thermal decomposition of Fe(CO)5 in Declin (carrier liquid) in the presence of oleic acid (surfactant). The magnetic particles consist of an amorphous iron-carbon alloy. For TEM investigation a droplet of the fluid was added to benzine and a carbon film on a copper net was immersed. When exposed to air the sample starts burning. The oxidation and electron irradiation transform the magnetic particles into hematite (α-Fe2O3) particles with a median diameter ø = 6.9 nm.

Intestinal Absorption of Iodine131-Labeled Triolein and Oleic Acid in Normal Subjects and in Steatorrhea

1958 ◽  
Vol 34 (5) ◽  
pp. 901-909 ◽  
Author(s):  
Ervin Kaplan ◽  
Bernard D. Edidin ◽  
Robert C. Fruin ◽  
Lyle A. Baker
Keyword(s):  
Oleic Acid ◽  
Intestinal Absorption ◽  
Normal Subjects

Oleic acid

2015 ◽  
Author(s):  
LB Becnel ◽  
YF Darlington ◽  
S Orechsner ◽  
J Easton-Marks ◽  
CA Watkins ◽  
...  
Keyword(s):  
Oleic Acid

Reusability Study of Sulfated Zirconia Functionalized SBA-15 Catalyst for Biolubricant Oil Production from Oleic Acid

2019 ◽  
Vol 1 (1) ◽  
pp. 46
Author(s):  
F R Rangganita ◽  
L Hermida ◽  
A Angraeni ◽  
D Khoirunnisa
Keyword(s):  
Oleic Acid ◽  
Sulfated Zirconia ◽  
Room Temperature ◽  
Oil Production ◽  
Catalyst Reusability

Sulfated zirconia functionalized SBA-15 catalsyt (SZr-SBA-15) was prepared byreacting SBA-15 with Zirkoniumoxychloride and urea at 90oC to form ZrO2-SBA-15. Then, ZrO2-SBA-15 was reacted with H2SO4 at room temperature to produceSZr-SBA-15 catalsyt.. The catalyst was characterized in terms of adsorptiondesorption nitrogen analysis, SEM-EDX and FTIR. Based on SEM-EDX andadsorption-desorption nitrogen analysis results, it was found that Zr had beenincorporated in SBA-15. By using the SZr-SBA-15 catalyst, esterification reactionof oleic acid with TMP to produce biolubricant oil of Trimethylolpropanetrioleatachieved 85% oleic acid conversion and selectivity of 63,7%. Reusability study ofSZr-SBA-15 catalyst was carried out for 3 rounds of reaction. It was found that thecatalyst could be used up to 3 rounds without significant decrease in activityKeywords: biolubricant oil, catalyst reusability, sba-15, sulfated zirconia.

PEMBUATAN SURFAKTAN DARI ASAM OLEAT

2019 ◽  
Vol 1 (3) ◽  
pp. 68
Author(s):  
Puguh Setyopratomo ◽  
Edy Purwanto ◽  
H. Yefrico ◽  
H. Yefrico
Keyword(s):  
Oleic Acid ◽  
Optimum Condition ◽  
Reaction Temperature ◽  
Catalyst Concentration ◽  
Acid Number ◽  
Esterification Reaction ◽  
Number Density ◽  
Sample Analysis ◽  
Reaction Conversion ◽  
Glycerol Mono

The synthesis of glycerol mono oleic from oleic acid and glycerol is classified as an esterification reaction. This research is aimed to study the influent of reaction temperature and catalyst concentration on reaction conversion. During the experiment the temperature of reaction mixture was varied as 110 oC, 130 oC, and 150 oC, while the catalyst concentration of 1%, 3 %, and 5% was used. The batch experiment was conducted in a glass reactor equipped with termometer, agitator, and reflux condensor. The oleic acid – glycerol mol ratio of 1 : 2 was used as a mixture feed. To maintain the reaction temperature at certain level, the oil bath was used. After the temperature of reaction mixture was reached the expected value, then H2SO4 catalyst was added to the reactor.  To measure the extent of the reaction, every 30 minutes the sample was drawn out from the reactor vessel. The sample analysis include acid number, density, and viscosity measurement. From this research the optimum condition which is the temperature of reaction of 150 oC and 1% catalyst concentration was obtained. At this optimum condition the convertion reach 86% and the analysis of other physical properties of the product show the acid number of 24.12, the density of 0.922 g/cc, and the viscosity of 118.4 cp.

BODIPY Fluorophores for Membrane Potential Imaging

2019 ◽  
Author(s):  
Jenna Franke ◽  
Benjamin Raliski ◽  
Steven Boggess ◽  
Divya Natesan ◽  
Evan Koretsky ◽  
...  
Keyword(s):  
Mammalian Cells ◽  
Water Solubility ◽  
Water Soluble ◽  
Voltage Sensitivity ◽  
Chemical Transformations ◽  
Direct Modification ◽  
Biological Compatibility ◽  
Meso Position ◽  
Ionizable Groups ◽  
Boron Center

Fluorophores based on the BODIPY scaffold are prized for their tunable excitation and emission profiles, mild syntheses, and biological compatibility. Improving the water-solubility of BODIPY dyes remains an outstanding challenge. The development of water-soluble BODIPY dyes usually involves direct modification of the BODIPY fluorophore core with ionizable groups or substitution at the boron center. While these strategies are effective for the generation of water-soluble fluorophores, they are challenging to implement when developing BODIPY-based indicators: direct modification of BODIPY core can disrupt the electronics of the dye, complicating the design of functional indicators; and substitution at the boron center often renders the resultant BODIPY incompatible with the chemical transformations required to generate fluorescent sensors. In this study, we show that BODIPYs bearing a sulfonated aromatic group at the meso position provide a general solution for water-soluble BODIPYs. We outline the route to a suite of 5 new sulfonated BODIPYs with 2,6-disubstitution patterns spanning a range of electron-donating and -withdrawing propensities. To highlight the utility of these new, sulfonated BODIPYs, we further functionalize them to access 13 new, BODIPY-based voltage-sensitive fluorophores. The most sensitive of these BODIPY VF dyes displays a 48% ΔF/F per 100 mV in mammalian cells. Two additional BODIPY VFs show good voltage sensitivity (≥24% ΔF/F) and excellent brightness in cells. These compounds can report on action potential dynamics in both mammalian neurons and human stem cell-derived cardiomyocytes. Accessing a range of substituents in the context of a water soluble BODIPY fluorophore provides opportunities to tune the electronic properties of water-soluble BODIPY dyes for functional indicators.

Strongly Coupled Redox-Linked Conformational Switching at the Active Site of the Non-Heme Iron-Dependent Dioxygenase, TauD

2019 ◽  
Author(s):  
Christopher John ◽  
Greg M. Swain ◽  
Robert P. Hausinger ◽  
Denis A. Proshlyakov
Keyword(s):  
Active Site ◽  
Structural Model ◽  
Heme Iron ◽  
Chemical Transformations ◽  
Experimental Conditions ◽  
Strongly Coupled ◽  
Non Heme Iron ◽  
Reversible Redox ◽  
Wide Range ◽  
Complex Structural

2-Oxoglutarate (2OG)-dependent dioxygenases catalyze C-H activation while performing a wide range of chemical transformations. In contrast to their heme analogues, non-heme iron centers afford greater structural flexibility with important implications for their diverse catalytic mechanisms. We characterize an <i>in situ</i> structural model of the putative transient ferric intermediate of 2OG:taurine dioxygenase (TauD) by using a combination of spectroelectrochemical and semi-empirical computational methods, demonstrating that the Fe (III/II) transition involves a substantial, fully reversible, redox-linked conformational change at the active site. This rearrangement alters the apparent redox potential of the active site between -127 mV for reduction of the ferric state and 171 mV for oxidation of the ferrous state of the 2OG-Fe-TauD complex. Structural perturbations exhibit limited sensitivity to mediator concentrations and potential pulse duration. Similar changes were observed in the Fe-TauD and taurine-2OG-Fe-TauD complexes, thus attributing the reorganization to the protein moiety rather than the cosubstrates. Redox difference infrared spectra indicate a reorganization of the protein backbone in addition to the involvement of carboxylate and histidine ligands. Quantitative modeling of the transient redox response using two alternative reaction schemes across a variety of experimental conditions strongly supports the proposal for intrinsic protein reorganization as the origin of the experimental observations.

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