All used in this research reagents were commercially available materials and were used without further purification. (R,S)-Ibuprofen (>98%) was provided from Am-Beed (Arlington Heights, IL, USA). Thionyl chloride (99.5%) was obtained from Acros Organics (Geel, Belgium). l -Histidine (≥99%) and l -phenylalanine (>98.5%) were purchased from Carl Roth (Karlsruhe, Germany). l -Tyrosine, acetonitrile (≥99.9%) for HPLC gradient grade, deuterated DMSO (99.9%), 2-ethylhexyl acrylate (2-EHA) (98%), isobornyl methacrylate (IBOMA) (>99%), azobis(isobutyronitrile) (AIBN) (99%), and n-octanol (≥99%) were provided by Sigma-Aldrich (Steinheim am Albuch, Germany). l -Tryptophan was provided by Tokyo Chemical Industry Co., Ltd (TCI, Tokyo, Japan). Propanol (PrOH), ammonium hydroxide solution 25% (NH3·H2O), anhydrous sodium sulfate, n-hexane, methylene chloride, and diethyl ether were high-purity obtained from Chempur (Gliwice, Poland). 4-Acryloyloxy benzophenone (ABP) was obtained from POLY-CHEM BmbH (Bitterfeld-Wolfen, Germany). Acrylic acid (AA) (>98%), ethanol (EtOH), chloroform, toluene, and ethyl acetate were of analytical grade purchased from StanLab (Lublin, Poland). Deuterated chloroform (CDCl3) (99.8%) (+0.03% TMSCl) was purchased from Eurisotop (Cheshire, England).
L phenylalanine
Manufactured by Carl Roth
Sourced in Germany
L-phenylalanine is a naturally occurring amino acid. It is a colorless crystalline powder and serves as a building block for proteins.
Automatically generated - may contain errors
Lab products found in correlation
Acetonitrile, by Merck Group (3 mentions)
L tyrosine, by Carl Roth (2 mentions)
Diethyl ether, by Chempur (1 mentions)
Isobornyl methacrylate, by Merck Group (1 mentions)
Thionyl chloride, by Thermo Fisher Scientific (1 mentions)
Sodium sulfate anhydrous, by Chempur (1 mentions)
Methylene chloride, by Chempur (1 mentions)
Toluene, by EKF Diagnostics (1 mentions)
N octanol, by Merck Group (1 mentions)
Deuterated chloroform cdcl3, by Eurisotop (1 mentions)
N hexane, by Chempur (1 mentions)
L histidine, by Carl Roth (1 mentions)
Deuterated dmso, by Merck Group (1 mentions)
2 ethylhexyl acrylate 2 eha, by Merck Group (1 mentions)
L tyrosine, by Merck Group (1 mentions)
Azobisisobutyronitrile, by Merck Group (1 mentions)
Betulinic acid, by Merck Group (1 mentions)
L serine, by Carl Roth (1 mentions)
L cysteine, by Carl Roth (1 mentions)
L phenylalanine, by Thermo Fisher Scientific (1 mentions)
6 protocols using l phenylalanine
1
Synthesis and Characterization of Ibuprofen Derivatives
2
Betulinic Acid Derivatization and Amino Acid Characterization
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Unless otherwise specified, all reagents and materials used were obtained without additional purification from commercial suppliers. Betulinic acid (BA) (≥98%), 1-octanol, and acetonitrile (for HPLC, gradient grade) were obtained from Sigma-Aldrich (Steinheim am Albuch, Germany). L-aspartic acid, L-isoleucine, L-leucine, L-methionine, L-proline, L-threonine, and L-valine of purity ≥98% were purchased from FluoroChem (Derbyshire, UK). L-serine (≥98.5%), L-phenylalanine (≥98.5%), L-proline (≥98.5%), and L-cysteine (≥98%) were provided by Carl Roth (Karlsruhe, Germany). L-alanine (>99.0%) was acquired from Bachem (Bubendorf, Switzerland) and L-lysine (≥98.0%, anhydrous) from Glentham Life Sciences (Corsham, UK). L-phenylalanine (99%) was provided by Alfa Aesar (Ward Hill, MA, USA). L-tryptophan (>98.5%) was purchased from TCI. Thionyl chloride (99.5%) was provided by Across Organic Geel (Geel, Belgium). Ammonium hydroxide solution 25% (NH3.H2O) of analytical grade was purchased from StanLab (Lublin, Poland). Ethanol (99.8%) was provided by Merck (Darmstadt, Germany). Methylene chloride and DMSO of high purity were provided by Chempur (Gliwice, Poland). Deuterated dimethyl sulfoxide (DMSO-d6) (99.8%) was obtained from Deutero GMBH (Kastellaun, Germany).
3
Quantitative Analysis of Phenolic Compounds
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Methanol, acetonitrile, external standards, such as gallic acid, chlorogenic acid, β- coumaric acid, with a purity of 99.5%, were purchased from Sigma-Aldrich and Fluka (Warsaw, Poland). Tween 20, L-tryptophan, L-phenylalanine, L-tyrosine were purchased from Carl Roth (Karlsruhe, Germany).
4
Fluorinated Amino Acid Synthesis
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4‐Benzyl‐L‐aspartate, 4‐nitrophenyl chloroformate, dithiothreitol, trifluoromethanesulfonic acid, and trifluoroacetic acid were obtained from TCI (Eschborn, Germany). L‐phenylalanine was purchased from Carl Roth (Karlsruhe, Germany). S‐carbobenzoxy‐L‐cysteine was obtained from BLD Pharmatech GmbH. Anhydrous dimethylacetamide (DMAc) was obtained from Acros (Geel, Belgium). S‐Benzyl‐L‐cysteine, hydrogen peroxide, and n‐butylamine were purchased from Alfa Aesar (Kandel, Germany). PFD was obtained from Fluorochem Chemicals (Derbyshire, UK). Methanol, ethyl acetate and diethyl ether were purchased from Fisher Scientific (Schwerte, Germany). Finally, n‐hexane and dichloromethane were obtained from VWR International (Darmstadt, Germany) and acetonitrile was purchased from Carl Roth (Karlsruhe, Germany).
5
Amino Acid Depletion in MEFs
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Human cancer cell lines were obtained from ATCC. MEFs eIF2αS51 A/S51 A (AA-MEFs) and the corresponding controls, MEFs eIF2αS51 /S (SS-MEFs)53 were obtained from the R. Kaufman laboratory. Cells were cultivated in DMEM (Gibco) supplemented with 10% FCS (Gibco), 100 U/ml penicillin and 100 µg/ml streptomycin (Gibco).
For essential amino acid depletion, cells were cultured for 24 h in DMEM without amino acids (Thermo Fisher Scientific) supplemented with all amino acids at the concentrations of regular DMEM but lacking each essential amino acid. Regular DMEM (Gibco) and DMEM without amino acids (Thermo Fisher Scientific) supplemented with all amino acids at the concentrations of regular DMEM were used as controls. L-Arginine, L-Glutamine, L-Histidine, L-Serine, L-Threonine, L-Valine and L-Isoleucine were all from Genaxxon, L-Tryptophan, L-Cysteine, L-Leucine and L-Lysine were all from Sigma-Aldrich, L-Glycine, L-Phenylalanine and L-Tyrosine were from Carl Roth, and L-Methionine was from Usbiologicals. All media were supplemented with 10% dialyzed FCS (Gibco).
For essential amino acid depletion, cells were cultured for 24 h in DMEM without amino acids (Thermo Fisher Scientific) supplemented with all amino acids at the concentrations of regular DMEM but lacking each essential amino acid. Regular DMEM (Gibco) and DMEM without amino acids (Thermo Fisher Scientific) supplemented with all amino acids at the concentrations of regular DMEM were used as controls. L-Arginine, L-Glutamine, L-Histidine, L-Serine, L-Threonine, L-Valine and L-Isoleucine were all from Genaxxon, L-Tryptophan, L-Cysteine, L-Leucine and L-Lysine were all from Sigma-Aldrich, L-Glycine, L-Phenylalanine and L-Tyrosine were from Carl Roth, and L-Methionine was from Usbiologicals. All media were supplemented with 10% dialyzed FCS (Gibco).
6
Antioxidant and Glycation Assay Reagents
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2,2-Diphenyl-1-picrylhydrazyl (DPPH • ), 2,2-azinobis-3-ethyl benzothiazoline-6-sulphonic acid (ABTS), 6-hydroxy-2,5,7,8,-tetramethylchromane-2-carboxylic acid (Trolox), 2,2'-azobis(2methylpropionamidine) dihydrochloride (AAPH), diethylene glycol, sodium borohydride, boric acid, nonafluoropentanoic acid (NFPA), trichloroacetic acid (TCA), D (+)-lactose monohydrate, acetonitrile (HPLC grade), rutin, quercetin-3-O-glucoside, quinic acid, p-coumaric, caffeic and gallic acids, Folin-Ciocalteu phenol reagent and Milli-Q water were from Sigma-Aldrich (St.
Louis, MO, USA). (+)-Catechin reference was purchased from Chromadex (Irvine, California, USA), chlorogenic acid, L-phenylalanine and glucose were from Roth (Karlsruhe, Germany); fluorescein sodium salt (FL) from Fluka Chemicals (Steinheim, Germany). Heterocyclic amines,
and PhIP were purchased from Toronto Research Chemicals Inc. (Toronto, Canada). CML, d2-CML and furosine were purchased from PolyPeptide Laboratories (Strasbourg, France).
Creatinine was from Alfa Aesar (Karlsruhe, Germany). Bond Elut PRS LRC cartridges and Bond-Elut C18 cartridges were purchased from Agilent Technologies (Lake Forest, CA, USA).
Chromabond XTR cartridges were from Macherey-Nagel GmbH & Co. (Bethlehem, PA, USA).
Oasis HLB cartridges for CML and furosine stable isotope dilution assay were purchased from Waters Corporation (Milford, CA, USA).
Louis, MO, USA). (+)-Catechin reference was purchased from Chromadex (Irvine, California, USA), chlorogenic acid, L-phenylalanine and glucose were from Roth (Karlsruhe, Germany); fluorescein sodium salt (FL) from Fluka Chemicals (Steinheim, Germany). Heterocyclic amines,
and PhIP were purchased from Toronto Research Chemicals Inc. (Toronto, Canada). CML, d2-CML and furosine were purchased from PolyPeptide Laboratories (Strasbourg, France).
Creatinine was from Alfa Aesar (Karlsruhe, Germany). Bond Elut PRS LRC cartridges and Bond-Elut C18 cartridges were purchased from Agilent Technologies (Lake Forest, CA, USA).
Chromabond XTR cartridges were from Macherey-Nagel GmbH & Co. (Bethlehem, PA, USA).
Oasis HLB cartridges for CML and furosine stable isotope dilution assay were purchased from Waters Corporation (Milford, CA, USA).
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