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Anthranilic acid

Anthranilic acid, also known as 2-Aminobenzoic acid, is a naturally occurring organic compound with the chemical formula C6H7NO2.
It is a white crystalline solid with a distinctive odor and is an important intermediate in the synthesis of various pharmaceuticals, dyes, and other industrial chemicals.
Anthranilic acid plays a crucial role in the metabolism of tryptophan and is involved in the production of niacin, a essential B-vitamin.
It has been studied for its potential therapeutic applications in areas such as pain management, inflammation reduction, and neurological disorders.
Researchers can leverage PubCompare.ai to optimzie their anthranilic acid-related research, locating the best protocols from literature, preprints, and patents using AI-driven comparisons to enhance reproducibility and accuracy, and streamline their research workflow to achieve greater results.

Most cited protocols related to «Anthranilic acid»

Mass spectrometry-based metabolomics profiling was performed on frozen prostate cell pellets (∼10 million cells). The process of metabolite extraction involved introduction of equimolar mixture of 11 standard compounds dissolved in methanol (Epibrassinolide, [D3] Testosterone, [15N] Anthranilic acid, Zeatine, Jasmonic acid, Gibberelic acid, [D4] Estrone, [15N]-Tryptophan, [D4] Thymine, [13C] Creatinine and [15N] Arginine) followed by homogenization of the cells. The homogenate was then subjected to extraction with sequential use of aqueous (chilled water) and organic (chilled methanol and chloroform) solvents in the following ratio 1∶4∶3∶1 (water∶methanol∶chloroform∶water) [28] . The resulting extracts were de-proteinized using a 3 KDa molecular filter (Amicon Ultracel -3K Membrane, Millipore Corporation, Billerica, MA) and the filtrate containing metabolites were dried under vacuum (Genevac EZ-2plus, Gardiner, NY). Prior to mass spectrometry analysis, the dried extract was resuspended in identical volume of injection solvent composed of water∶methanol (50∶50) with 0.2% acetic acid and subjected to liquid chromatography (LC) mass spectrometry. As additional controls to monitor the profiling process, an equimolar mixture of 11 standard compounds (Epibrassinolide, [D3] Testosterone, [15N] Anthranilic acid, Zeatine, Jasmonic acid, Gibberelic acid, [D4] Estrone, (15N) Tryptophan, [D4] Thymine, [13C] Creatinine, and [15N] Arginine) and a characterized pool of mouse liver (extracted in tandem with cell lines) were analyzed along with the cell line samples. Each of these controls, were included multiple times into the randomization scheme such that samples preparation and analytical variability could be constantly monitored. Furthermore, analysis of each cell line was succeeded by at least two blank runs, to prevent any carryover of metabolites between samples. Figure S1 illustrates the reproducibility in the profiling process monitored using the standard mixture described above. Notably the CV for the entire profiling process measured using five independent replicates of the mouse liver extract mentioned above was less than 5%.
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Publication 2011
Acetic Acid Acids anthranilic acid Arginine Cell Lines Cells Chloroform Creatinine Estrone Freezing jasmonic acid Liquid Chromatography Liver Liver Extracts Mass Spectrometry Methanol Mus Pellets, Drug Prostate Solvents Testosterone Thymine Tissue, Membrane Tryptophan Vacuum
Synthesis of modified oligodeoxyribonucleotides (ONs) was performed on an DNA synthesizer using 0.2 μmol scale succinyl linked LCAA-CPG (long chain alkyl amine controlled pore glass) columns with a pore size of 500Å. Standard protocols for incorporation of DNA phosphoramidites were used. A ~50-fold molar excess of modified phosphoramidites in anhydrous acetonitrile (at 0.05 M) was used during hand-couplings (performed to conserve material) except with 4Z (~70-fold molar excess in anhydrous CH2Cl2, at 0.07M). Moreover, extended oxidation (45s) and coupling times were used (0.01 M 4,5-dicyanoimidazole as activator, 15 min for monomers V/W/Y, 35 min for monomer Z; 0.01 M 5-(bis-3,5-trifluoromethylphenyl)-1H-tetrazole [Activator 42], 15 min for monomers Q/S/V). Cleavage from solid support and removal of protecting groups was accomplished upon treatment with 32% aq. ammonia (55 °C, 24 h). Purification of all modified ONs was performed to minimum 80% purity using either of two methods: a) overall synthesis yield >80%: cleavage of DMT using 80% aq. AcOH, followed by precipitation from acetone (−18 °C for 12-16 h) and washing with acetone, or b) overall synthesis yield <80%: purification of ONs by RP-HPLC as described below, followed by detritylation and precipitation as outlined under “a”.
Purification of the crude ONs was performed on a HPLC system equipped with an XTerra MS C18 pre-column (10 μm, 7.8 × 10 mm) and a XTerra MS C18 column (10μm, 7.8 × 150 mm) using the representative gradient protocol depicted in Table S1. The identity of synthesized ONs was established through MALDI-MS/MS analysis (Table S2-S3) recorded in positive ions mode on a Quadrupole Time-Of-Flight Tandem Mass Spectrometer equipped with a MALDI source using anthranilic acid as a matrix, while purity (>80%) was verified by RP-HPLC running in analytical mode.
Publication 2011
1H-tetrazole Acetone acetonitrile Amines Ammonia Anabolism anthranilic acid Cytokinesis High-Performance Liquid Chromatographies Ions Molar Oligodeoxyribonucleotides phosphoramidite Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Tandem Mass Spectrometry
The ZIKV-Nanoluciferase (Nanoluc) construct (Fig. 1A) used in these assays was described previously34 (link). For maintenance and propagation of the plasmid containing the pCCI-SP6-ZIKV-Nanoluc, the E. coli Turbo strain (New England Biolabs) was used.
Complete amplification of the viral genome was performed using a PCR reaction with Phusion High Fidelity (Thermo Fisher) enzyme and the designed primers ZIKV-Forward (5′ CG ATT AAG TTG GGT AAC GCC AGG GT 3′) and ZIKV-Reverse (5′ T AGA CCC ATG GAT TTC CCC ACA CC 3′). The PCR product containing SP6 promoter followed by complete viral cDNA was purified with the DNA clean and concentration kit (Zymo Research). In vitro transcription was performed using the RiboMAX™ Large-scale RNA Production Systems kit (Promega), as instructed by the manufacturers.
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Publication 2019
Biological Assay DNA, Complementary Enzymes Escherichia coli Oligonucleotide Primers Plasmids Promega Strains Transcription, Genetic Viral Genome Zika Virus
Constructs, Cell Culture, and Transfection—The construct
encoding human TRPM2 (8 (link)) with a
C-terminal EE epitope (29 ) was
used. Mutations were introduced using QuikChange system (Stratagene) and
confirmed by sequencing. The constructs encoding subunit concatemers with a
C-terminal EE epitope were made as follows. Firstly, the sequence (nucleotides
1–700) encoding part of the TRPM2 N terminus (TRPM2N) was amplified by
PCR using Pfu and forward primer
5′-TCTCTAGAATGGAGCCCTCAGCCCTGAGG-3′ (XbaI
sequence underlined and TRPM2 sequence in italic) and reverse primer
5′-TCAGTACAGGTAGAGCAAGGTGTCC-3′. The resultant PCR product
containing XbaI site was inserted into pCR2.1 following the manufacturer's
instructions (Invitrogen) to generate TRPM2N-pCR2.1. Secondly, the vector
sequence between EcoRI and XbaI and the TRPM2 sequence between XbaI and SacI
were separately excised from TRPM2N-pCR2.1 and ligated with the sequence
between SacI and EcoRI from TRPM2-EE-pcDNA3.1 to generate TRPM2-EE-pCR2.1.
Finally, the TRPM2-EE sequence between XbaI and HindIII was excised from
TRPM2-EE-pCR2.1 to replace the sequence between XbaI and PmeI in
TRPM2-Myc-pcDNA3.1 to produce the constructs encoding concatenated subunits
(see Fig. 4A).
Maintenance of human embryonic kidney cells (HEK293) and transient
transfection with plasmids were described previously
(29 ).
Biotin Labeling and Western Blotting Analysis—Experiments
were performed as described previously
(29 ,
30 (link)). Proteins were resolved on
SDS-PAGE gels and detected using primary rabbit anti-EE antibody (1:2000
dilution; Bethyl Laboratories) and secondary goat horseradish
peroxidase-conjugated anti-rabbit IgG antibody (1:2000 dilution; Santa Cruz
Biotechnology).
Electrophysiological Recording—Whole-cell recordings were
made using an Axopatch 200B amplifier at room temperature 24–48 h after
transfection as described previously
(29 ,
30 (link)). The data were filtered at
2 kHz and sampled at 10 kHz. Cells were held at –40 mV and voltage ramps
with a 1-s duration from –120 mV to 80 mV were applied every 5 s. The
currents at –80 mV denoted in the figures by circles (see Figs.
1, B and C,
3, A–D, and
4, C and D)
were obtained from the current responses to voltage ramps. In some
experiments, cells were held constantly at –40 mV or 40 mV, and the
currents were plotted as continuous lines (see
Fig. 3E).
Intracellular solution contained (in mm): 147 NaCl, 0.05 EGTA, 1
MgCl2, 10 HEPES, 1 Na2ATP, and 1 ADPR.
Table 1 lists the compositions
of extracellular solutions used. Flufenamic acid (FFA) (0.5 mm)
(31 (link)) or
N-(p-amylcinnamoyl) anthranilic acid (20 μm)
(32 (link)) was applied at the end of
each recording via a RSC-160 system (Biologic Science Instruments) to confirm
TRPM2 channel-mediated currents.

Compositions of extracellular recording solutions (in
mm)

Solutions
NaClKClMgCl2CaCl2HEPESGlucose
Standard
147
2
1
2
10
13
147 NaCl + 2 CaCl2 + 1 MgCl2 147
0
1
2
10
13
147 NaCl (no CaCl2)
147
0
0
0
10
24
147 NaCl + 0.1 CaCl2 147
0
0
0.1
10
24
147 NaCl + 0.3 CaCl2 147
0
0
0.3
10
22
147 NaCl + 1 CaCl2 147
0
0
1
10
21
147 NaCl + 2 CaCl2 147
0
0
2
10
17
147 NaCl + 3 CaCl2 147
0
0
3
10
11
147 NaCl + 10 CaCl2 147
0
0
10
10
0
147 NaCl + 2 MgCl2 147
0
2
0
10
20
110 CaCl2 0
0
0
110
10
24
110 MgCl2 0
0
110
0
10
24
The reversal or zero-current potentials (Er) were
determined from current responses to the aforementioned voltage ramps. After
cell-attached configuration was established in standard extracellular
solution, application of voltage ramps started and continued throughout
experiments, during which whole-cell configuration was achieved at least 2 min
after the external solution was replaced with the indicated extracellular
solutions. The flufenamic acid/anthranilic acid-insensitive current components
were negligible (e.g. Fig.
1B
), and no subtraction from the total currents was made.
The reversal potentials were corrected for liquid junction potentials as we
described previously (33 (link)). Ion
activities were used, converted from ion concentrations using the following
coefficients: γNa = 0.75, γCa = 0.28, and
γMg = 0.34. The relative permeability
PX/PNa (X = calcium or
magnesium) were derived using the Goldman-HodgkinKatz equation
(8 (link),
23 (link)):
PX/PNa = [Na]i exp(ErF/RT)(1 + exp
(ErF/RT))/4[X]o,
where F, R, and T are Faraday constant, gas constant, and
absolute temperature.
Data Analysis—All the data, where appropriate, are presented
as mean ± S.E. The calcium inhibition was estimated by fitting to the
Hill equation: I/I (%) = (100–C)/[1+
([calcium]/IC50)n], where I is the
sustained current as a percentage of the peak current (Ip),
C is the Ca2+-insensitive current component,
IC50 is the concentration producing half-maximal inhibition, and
n is the Hill coefficient. Curve fitting was carried using Origin
(OriginLab, Northampton, MA). Comparisons were made using the Student's
t test between two groups or analysis of variance (post hoc Tukey)
between multiple groups with significance at the level of p <
0.05.
Publication 2008
All reagents and KP metabolites were analytical reagent grade and were purchased from Sigma-Aldrich (St Louis, MO), unless otherwise stated. Deuterated internal standards were purchased from Medical Isotopes, Inc (Pelham, NH). KP metabolites were extracted using 10% (w/v) trichloroacetic acid (TCA) with equal volume of serum samples in accordance with methods previously described15 . CSF samples were prepared similarly to serum samples except that deproteinization with TCA was not performed.
Concurrent analysis of tryptophan, kynurenine, 3-hydroxykynrenine (3-HK), 3-hydroxyanthranilic acid (3-HAA), and anthranilic acid (AA) was performed with UHPLC as described by Jones et al.16 (link), using an injection volume of 20 μL of the prepared extract from each samples. KA detection was performed using a gradient mobile phase comprise of 50 mM sodium acetate buffer supplement with 25 mM zinc acetate (dihydrate) to enhance fluorescence intensity and 2.25% acetonitrile as organic modifier (Solvent A), and 10% acetonitrile (Solvent B). Each sample (10 μL) was injected into a Poroshell RRHT C-18, 1.8 μm 2.1 × 100 mm column (Agilent Technologies, Inc, Santa Clara, CA) maintained at 38 °C for 12 min run time at a unison flowrate of 0.75 mL/min. The gradient elution consisted of 100% solvent A for 3 min and then 50% solvent A and 50% solvent B for 2 min, followed by 100% B for 2 min and 100% solvent A (run time 10 min). This gradient ensures sufficient time for KA retention while minimizing potential build-up of pressure due to precipitation of the high salt buffer. Detection of KA used fluorescence (excitation and emission wavelengths of 344 and 388 nm, respectively with a retention time of 1.5 min). Agilent OpenLAB CDS ChemStation (Edition C.01.04) was used to analyze the chromatograms (Supplementary Figure S1A and B).
For GCMS, 50 μL of the prepared extract were derivatized. Concurrent analysis of PA and QA were carried out as described by Smythe et al.17 (link) with slight modification using an Agilent 7890 A GC system coupled with Agilent 5975 C mass spectrometry detector and Agilent 7693 A autosampler (Agilent Technologies, Inc, Santa Clara, CA) with one microliter of derivatized mixture. Separation of PA and QA were achieved with a DB-5MS column, 0.25 μm film thickness, 0.25 mm × 30 m capillary column (Agilent Technologies, Inc, Santa Clara, CA) within 7 min but the assay run time was set for 12 min to prevent sample carryover. Concentrations of PA and QA were analyzed using Agilent GC/MSD ChemStation software (Edition 02.02.1431) and interpolated from the established six-point calibration curves based on the abundance count ratio of the metabolites to their corresponding deuterated internal standards within each standards and samples (Supplementary Figure S1C and D).
The intra- and inter-assay CV was within the acceptable range of 4–8% for UHPLC assays and 7–10% for GCMS assays calculated from the repeated measures of the metabolites standards incorporated during the sequence run. Nicotinamide adenine dinucleotide (NAD+) was measured with 20 μL of neat serum using a previously described method18 (link).
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Publication 2017
3-Hydroxyanthranilic Acid acetonitrile anthranilic acid Biological Assay Buffers Capillaries Coenzyme I Dietary Supplements Fluorescence Gas Chromatography-Mass Spectrometry Isotopes Kynurenine Mass Spectrometry Pressure Retention (Psychology) Serum Sodium Acetate Sodium Chloride Solvents Trichloroacetic Acid Tryptophan Zinc Acetate

Most recents protocols related to «Anthranilic acid»

In a round bottom flask fitted with condenser carrying 10 mL of solvent (Dichloroethane), 0.3 g of aromatic monomer (anthranilic acid), 1 mL of cross-linker (CCl4) and 0.3 g of Ferric Chloride (FeCl3), used as a catalyst, were continuously mixed and heated in an oil bath. Initially, temperature was maintained at 45 °C for 4–5 h, and then raised to 80–85 °C for 19–20 h till product was formed. The thick paste like appearance indicates the syntheses of HCP-AA which was washed with ethanol till pure HCP-AA was obtained after the removal of excessive solvent and FeCl3 (washed until brown color of FeCl3 disappeared). After filtrations, purified product was collected in china dish and dried at 100 °C in an oven57 ,58 (link).
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Publication 2024
Anthranilic acid (monomer), Carbon tetrachloride (cross-linker), Dichloroethane (DCE) (solvent), Ferric chloride (catalyst), Ethanol and Chromium Chloride were obtained from Sigma Organics and used as received in their pure form.
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Publication 2024
Mannose was labelled with anthranilic acid (2-aminobenzoic acid) (2AA) through a Maillard reaction similarly to already reported [11] (link). Briefly, 6 mg of anthranilic acid (2AA) was dissolved in 100 µL of dimethyl sulfoxide: acetic acid (7:3, v: v) containing 1 M of sodium cyanoborohydride (NaBH 3 CN). Then, mannose (25.2 mg) was dissolved in the previously prepared solution. The resulting mixture was vigorously vortexed at maximum speed (Fisherbrand, USA), protected from light, and incubated for 12 h at 37 °C. After this time, the labelled mannose was diluted in acetate buffer, purified employing a cyano-modified silica gel-SPE column (Chromabond ® ), and lyophilized.
Proton nuclear magnetic resonance spectroscopy analysis ( 1 H-NMR) was conducted to confirm the labelling. For this purpose, fluorescently labelled mannose and unlabelled mannose were dissolved in deuterated water (D 2 O) obtained from Sigma Aldrich (St Louis, MO, USA) at 200 mM, while anthranilic acid was dissolved in deuterated dimethyl sulfoxide (DMSO-D6; Cambridge Isotope Laboratories, Inc. (Andover, MA, USA)) at the same concentration. The solutions were then placed in NMR tubes (600 µl) to be characterized using a Bruker NEO-750 equipment (Karlsruhe, Germany). (
Publication 2024

Example 1

TABLE 1
Amount (% w/w)
Example Example Example Example
IngredientsABCD
Tetrofosmin13.00-15.0013.14-14.5314.7214.19
Disulfosalicylate
Stannous  0.37-0.5 0.37-0.46 0.44 0.43
Chloride
Dihydrate
Sodium D-12.00-16.0012.65-15.4714.9714.43
Gluconate
Sodium 50.00-62.0050.59-61.8454.8952.91
Bicarbonate
Gentisic Acid*15.00-17.0013.54-15.0014.9718.03
*Para-amino benzoic acid, Maleic acid, Anthranilic acid can also be used

Procedure:

Approximately 90% of the total volume of Water for Injection (WFI) was added to a preparation vessel. The WFI was deoxygenated. Tetrofosmin, reducing agent selected from stannous chloride dihydrate, transchelator selected from Sodium D-gluconate, radioprotectant selected from Gentisic acid, para-amino benzoic acid, maleic acid, anthranilic acid and combinations thereof and sodium hydrogen carbonate were dissolved. The solution obtained was deoxygenated and final volume and the bulk solution was deoxygenated. The solution was sterile filtered. The vials were partially stoppered and then lyophilized.

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Patent 2024
Acids Amino Acids anthranilic acid Benzoic Acid Bicarbonate, Sodium Blood Vessel Dietary Fiber gentisic acid gluconate maleic acid Reducing Agents Sodium Sodium Chloride stannous chloride dihydrate Strains
An analytical protocol based on targeted LC-MS/MS was developed to measure tryptophan metabolites. The latter (with tryptophan) includes 5-hydroxytryptophan, serotonin, kynurenin, 3-hydroxy kynurenin, 3-hydroxy anthranilic acid, xantherunic acid, kynurenic acid, quinaldic acid, 8-hydroxy quinaldic acid, anthranilic acid, indol-3-acetic acid, tryptamine, indole-3-lactic acid, 5-hydroxy indole-3-acetic acid, quinolinic acid, picolinic acid, indole-3-carboxaldehyde, and indol-3-propionic acid. Serum or cecal content (50 µL) was mixed with 50 µL pure acetonitrile (for protein precipitation) containing deuterated compounds at 50 μ µM as an internal standard (CDN isotopes, Pointe-Claire, QC, Canada). The supernatant (50 µL) was then added to deionized water (600 µL). Ten microliters of this mixture were injected onto an UPLC-MS/MS system (Acquity TQ-XS Detector, Waters, Milford, MA) equipped with a C18-XB column (1.7 µm-100Å-150 × 2.1 mm from Phenomenex®, Torrance, USA). The ions of each analyzed compound were detected in positive ion mode using multiple reaction monitoring. The Masslinks software (Waters) was used for data acquisition and processing.
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Publication 2024

Top products related to «Anthranilic acid»

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Anthranilic acid is a chemical compound with the molecular formula C6H7NO2. It is a white crystalline solid that is soluble in water and organic solvents. Anthranilic acid is used as an intermediate in the production of various pharmaceutical and agricultural chemicals.
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Gibberellic acid is a plant hormone that belongs to the gibberellin family. It is a naturally occurring substance produced by various fungi and plants. Gibberellic acid plays a key role in the regulation of plant growth and development, including stem elongation, seed germination, and flower induction.
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Jasmonic acid is a naturally occurring plant hormone that plays a crucial role in plant growth and development. It is a carboxylic acid with the chemical formula C₁₂H₁₈O₃. Jasmonic acid functions as a signaling molecule, regulating various physiological processes in plants, including defense responses, stress tolerance, and reproductive development.
Thymine-d4 is a deuterated form of the DNA base thymine. It is a chemical compound used as a standard or label in research applications, such as mass spectrometry and nuclear magnetic resonance spectroscopy.
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Glutamic acid-d5 is a stable isotope-labeled amino acid. It is used as a reference standard and as a tracer compound in various analytical and research applications.
15N anthranilic acid is a stable isotope-labeled compound. It is a white crystalline solid used as a research tool in various scientific applications.
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Testosterone-d3 is a stable isotope-labeled compound used as an internal standard in analytical methods for the quantification of testosterone in biological samples. It serves as a reference substance to ensure accurate and reliable measurement of testosterone levels.
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Formic acid is a colorless, pungent-smelling liquid chemical compound. It is the simplest carboxylic acid, with the chemical formula HCOOH. Formic acid is widely used in various industrial and laboratory applications.
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Tryptophan-15N2 is a stable isotope-labeled amino acid product manufactured by Merck Group. It contains two nitrogen-15 atoms in the indole ring of the tryptophan molecule. This product is commonly used as a research tool in various scientific applications, such as metabolism studies and protein labeling.
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Acetonitrile is a colorless, volatile, flammable liquid. It is a commonly used solvent in various analytical and chemical applications, including liquid chromatography, gas chromatography, and other laboratory procedures. Acetonitrile is known for its high polarity and ability to dissolve a wide range of organic compounds.

More about "Anthranilic acid"

Anthranilic acid, also known as 2-Aminobenzoic acid, is a naturally occurring organic compound with the chemical formula C6H7NO2.
It is a white crystalline solid with a distinctive odor and is an important intermediate in the synthesis of various pharmaceuticals, dyes, and other industrial chemicals.
Anthranilic acid plays a crucial role in the metabolism of tryptophan, an essential amino acid, and is involved in the production of niacin, a vitamin B-complex.
Researchers have explored the potential therapeutic applications of anthranilic acid in areas such as pain management, inflammation reduction, and neurological disorders.
Closely related compounds like gibberellic acid, jasmonic acid, and thymine-d4 have also been studied for their biological and chemical properties.
Amino acids like glutamic acid-d5 and tryptophan-15N2 are often used in conjunction with anthranilic acid for various analytical and experimental purposes.
Leveraging the power of PubCompare.ai, researchers can optimize their anthranilic acid-related studies by locating the best protocols from literature, preprints, and patents using AI-driven comparisons.
This can enhance the reproducibility and accuracy of their experiments, while also streamlining their research workflow to achieve greater results.
Whether exploring the metabolism of anthranilic acid or developing new pharmaceutical applications, PubCompare.ai can be a valuable tool in the researcher's arsenal.