Dde-lysine was selectively deprotected by incubating the resin three times with 2% hydrazine hydrate in DMF for 3 min (400 r.p.m.), which also cleaved the Fmoc groups. Therefore, the N-terminus was protected by Boc in peptides not modified with fluorescein. Peptides were acylated at the lysine side chain by the addition of free fatty acid (2 equiv.), DCC (2 equiv.) and HOBt (4 equiv.) in 3 ml DMF and shaking at 400 r.p.m. for 1 h. Myristic acid, palmitic acid and stearic acid were purchased from Tokyo Chemical Industry (TCI).
Myristic acid
Manufactured by Tokyo Chemical Industry
Sourced in Japan
Myristic acid is a saturated fatty acid with the chemical formula CH3(CH2)12COOH. It is a solid at room temperature and is commonly used in the production of various chemical products, such as soap, cosmetics, and food additives.
Automatically generated - may contain errors
Lab products found in correlation
Palmitic acid, by Tokyo Chemical Industry (6 mentions)
Stearic acid, by Tokyo Chemical Industry (5 mentions)
Lauric acid, by Tokyo Chemical Industry (4 mentions)
Arachidic acid, by Tokyo Chemical Industry (2 mentions)
Oleic acid, by Merck Group (2 mentions)
Capric acid, by Fujifilm (2 mentions)
Octanoic acid, by Tokyo Chemical Industry (2 mentions)
Docosanoic acid, by Merck Group (1 mentions)
Decanoic acid, by Merck Group (1 mentions)
Tetracosanoic acid, by Merck Group (1 mentions)
Docosapentaenoic acid, by Merck Group (1 mentions)
Arachidic acid, by Merck Group (1 mentions)
9 decenoic acid, by Merck Group (1 mentions)
Perfluorooctanoic acid pfoa, by Merck Group (1 mentions)
Lc ms ms grade acetonitrile, by Merck Group (1 mentions)
Hplc grade hexane, by Merck Group (1 mentions)
Anti syntaxin, by Merck Group (1 mentions)
Anti akt, by Cell Signaling Technology (1 mentions)
Anti erk, by Cell Signaling Technology (1 mentions)
Anti p akt, by Cell Signaling Technology (1 mentions)
7 protocols using myristic acid
1
Site-Specific Peptide Acylation
2
Rubber Compound Preparation with Fatty Acids
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Isoprene rubber (IR2200) was supplied from JSR Co, Japan. Natural rubber (NR, RSS no. 1) was used. Elemental sulfur (S8, purity: 99.9%, powder: 150 mesh), ZnO (average diameter: 0.29 μm), N-cyclohexyl-2-benzothiazole sulfenamide (CBS, Sanceler CM-G), and zinc stearate (ZnSt2) were rubber-processing commercial grade and used as received. They were purchased from Hosoi Chemical Industry Co., Ltd., Tokyo, Japan, Sakai Chemical Industry Co., Ltd., Osaka, Japan, Sanshin Chemical Industry Co., Ltd., Yamaguchi, Japan, and FUJIFILM Wako Pure Chemical Corporation., Osaka, Japan, respectively. Different kinds of saturated fatty acid, i.e., lauric acid (LaH, C12, purity: >98.0%), myristic acid (MyH, C14, purity: >99.0%), palmitic acid (PaH, C16, purity: >99.5%), and arachidic acid (ArH, C20, purity: >98.0%) were purchased from Tokyo Chemical Industry Co., Tokyo, Japan. Stearic acid (StH, C18, LUNAC S-25) was supplied from Kao Co., Tokyo, Japan. All fatty acids were used as received.
3
Fatty Acid Quantification by LC-MS/MS
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The following chemicals were purchased from Tokyo Chemical Industry (Tokyo, Japan): n-octanoic acid (C8:0), lauric acid (C12:0), myristic acid (C14:0), palmitic acid (C16:0), cis-9-hexadecenoic acid (C16:1), stearic acid (C18:0), γ-linolenic acid (C18:3), cis-5,8,11,14,17-eicosapentaenoic acid (EPA; C20:5) and arachidonic acid (C20:4). Decanoic acid (C10:0), 9-decenoic acid (C10:1), oleic acid (C18:1), arachidic acid (C20:0), all-cis-7,10,13,16,19-docosapentaenoic acid (DPA, C22:5), docosanoic acid (C22:0), tetracosanoic acid (C24:0), hexacosanoic acid (C26:0), DAABD-AE, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC), 4-(dimethylamino) pyridine (DMAP) and perfluorooctanoic acid (PFOA) were purchased from Sigma-Aldrich (Taufkirchen, Germany). The following deuterium or 13C labeled analogs used as IS were purchased from Cambridge Isotopes Laboratories (Tewksbury, MA, USA): 13C4-C8:0, d3-C10:0, d3-C12:0, d3-C14:0, d4-C16:0 and d3-C18:0. PRA, PHA, d3-PRA, d3-PHA, d4-C22:0, d4-C24:0, and d4-C26:0 were obtained from Dr. H. J. Ten Brink (Vrije Universiteit Medical Center, Amsterdam, The Netherlands). LC-MS/MS grade acetonitrile and water were purchased from Merck (Darmstadt, Germany). Merck also supplied us with HPLC grade hexane, toluene, and heptane.
4
Lipid Signaling Modulators in Neuroinflammation
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BHB and sodium salts of capric acid, caprylic acid, LA, myristic acid, palmitic acid, and stearic acid were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Anti-ERK, anti-phosphorylated ERK (pERK), anti-Akt, anti-pAkt, anti-NFκB, anti-pNFκB, and U0126 were purchased from Cell Signaling Technology Inc. (Danvers, MA, USA). Anti- N-methyl-D-aspartate receptor type 2B (NR2B), anti-syntaxin, anti-β-actin, LPS (from Escherichia coli O111:B4), and poly-ethylenimine (PEI) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Cytarabine (AraC) was purchased from FUJIFILM-Wako Pure Chemical Corp. (Osaka, Japan). Anti-synaptophysin (Boehringer Mannheim GmbH, Mannheim, Germany) and anti-synaptosomal nerve-associated protein 25 (SNAP25) (Synaptic Systems, Germany) were also used in the study.
5
Bacterial Growth Inhibition Assay
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Lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, and glutaraldehyde were purchased from Tokyo Chemical Industry Co. Ltd. (Tokyo, Japan). Caprylic acid, capric acid, linoleic acid, SLS, sodium chloride (NaCl), disodium hydrogen phosphate 12-water (Na2HPO4•12H2O), potassium dihydrogen phosphate (KH2PO4), sodium chloride (KCl), potassium hydroxide (KOH), hydrochloric acid (HCl), manganese (II) chloride tetrahydrate (MnCl2•4H2O), magnesium sulfate heptahydrate (MgSO4•7H2O), iron (II) sulfate heptahydrate (FeSO4•7H2O), calcium chloride dihydrate (CaCl2•2H2O), agar, crystal violet, Hank’s balanced salt solution (HBSS)(+) and 99.5% ethanol (EtOH) were purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan). SLES was purchased from the NOF Corporation (Tokyo, Japan). The Dulbecco’s phosphate-buffered saline (d -PBS)(+) preparation reagent (with Ca and Mg) (100×) and fetal bovine serum (FBS) were purchased from Nacalai Tesque (Kyoto, Japan) and Thermo Fisher Scientific K.K. (Tokyo, Japan), respectively. WELPAS® antiseptic solution for hands (0.2%), an alcohol-based disinfectant, was purchased from Maruishi Pharmaceutical Co. Ltd. (Osaka, Japan).
6
Albumin Binding Interactions Studied
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Recombinant
human albumin was a gift from
Nipro Co. (Shiga, Japan). Warfarin and dansylsarcosine were purchased
from Sigma Chemical Company (St. Louis, MO). Using a modification
of the procedure reported by Chen,28 (link) albumin
was defatted with activated charcoal at 0 °C in an acidic solution,
deionized, and then freeze-dried. ARP was purchased from Tokyo Chemical
Industry Co Ltd. (Tokyo, Japan). Dehydro-ARP, the main active metabolite
of ARP, was synthesized according to the method of Zeidan et al.29 (link) 2-Deschloro-ARP was purchased from Toronto Research
Chemicals (Toronto, Canada). 3-Deschloro-ARP was synthesized according
to the published procedure.30 (link) Deschloro-ARP
was synthesized following a method reported by Banno et al.31 (link) Octanoic acid and myristic acid were purchased
from Tokyo Chemical Industry Co Ltd. (Tokyo, Japan). All other chemicals
were purchased from commercial sources and were of the highest grade
available. About 67 mM sodium phosphate buffer (pH 7.4) was used in
the equilibrium dialysis and spectroscopic (CD and fluorescence) experiments.
Stock solutions of ARP, its derivatives, Warfarin, and dansylsarcosine
(2.5 mM) were prepared in methanol.
human albumin was a gift from
Nipro Co. (Shiga, Japan). Warfarin and dansylsarcosine were purchased
from Sigma Chemical Company (St. Louis, MO). Using a modification
of the procedure reported by Chen,28 (link) albumin
was defatted with activated charcoal at 0 °C in an acidic solution,
deionized, and then freeze-dried. ARP was purchased from Tokyo Chemical
Industry Co Ltd. (Tokyo, Japan). Dehydro-ARP, the main active metabolite
of ARP, was synthesized according to the method of Zeidan et al.29 (link) 2-Deschloro-ARP was purchased from Toronto Research
Chemicals (Toronto, Canada). 3-Deschloro-ARP was synthesized according
to the published procedure.30 (link) Deschloro-ARP
was synthesized following a method reported by Banno et al.31 (link) Octanoic acid and myristic acid were purchased
from Tokyo Chemical Industry Co Ltd. (Tokyo, Japan). All other chemicals
were purchased from commercial sources and were of the highest grade
available. About 67 mM sodium phosphate buffer (pH 7.4) was used in
the equilibrium dialysis and spectroscopic (CD and fluorescence) experiments.
Stock solutions of ARP, its derivatives, Warfarin, and dansylsarcosine
(2.5 mM) were prepared in methanol.
7
Fatty Acid Profiling Protocol
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2-Nitrophenylhydrazine hydrochloride (2-NPH•HCl), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1-EDC•HCl), butyric acid (FA4:0), hexanoic acid (FA6:0), heptanoic acid (FA7:0), octanoic acid (FA8:0), undecanoic acid (FA11:0), lauric acid (FA12:0), myristic acid (FA14:0), palmitic acid (FA16:0), heptadecanoic acid (margaric acid, FA17:0), stearic acid (FA18:0), nonadecanoic acid (FA19:0), arachidic acid (FA20:0), tricosanoic acid (FA23:0), linOleic acid (FA18:2), and linolenic acid (FA18:3) were purchased from Tokyo Chemical Industry Co., Ltd (Tokyo, Japan). Oleic acid (FA18:1), arachidonic acid (FA20:4), eicosapentaenoic acid (EPA, FA20:5) and docosahexaenoic acid (DHA, FA22:6) were obtained from Sigma-Aldrich Japan (Tokyo, Japan). Capric acid (FA10:0), and HPLC grade methanol and water were from Wako Pure Chemical Industry (Osaka, Japan). FA labeling reagents were obtained from YMC CO (Kyoto, Japan).
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