4 mercaptophenylacetic acid

Manufactured by Merck Group

Sourced in Germany

4-mercaptophenylacetic acid is a chemical compound used as a laboratory reagent. It has the molecular formula C8H8O2S. The compound is a white crystalline solid at room temperature.

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Lab products found in correlation

Anhydrous hydrazine, by Merck Group (1 mentions) 5 6 carboxyfluorescein, by Merck Group (1 mentions) N n diisopropylcarbodiimide, by Merck Group (1 mentions) Fmoc l cys trt oh, by Gyros Protein Technologies (1 mentions) Fmoc l lys boc oh, by Gyros Protein Technologies (1 mentions) Fmoc l val oh, by Gyros Protein Technologies (1 mentions) Fmoc l leu oh, by Gyros Protein Technologies (1 mentions) Lc ms grade water with 0.1 formic acid, by Thermo Fisher Scientific (1 mentions) Oxyma pure, by Merck Group (1 mentions) Acetic anhydride, by Merck Group (1 mentions) Piperidine, by Merck Group (1 mentions) Tentagel r ram resin, by Rapp Polymere (1 mentions) Tribute peptide synthesizer, by Protein Technologies (1 mentions) Tris base, by Thermo Fisher Scientific (1 mentions) Guanidine hydrochloride, by Thermo Fisher Scientific (1 mentions) 4 nitrophenyl chloroformate, by Thermo Fisher Scientific (1 mentions) Fluorescein 5 maleimide, by Thermo Fisher Scientific (1 mentions) Nanodrop 2000c spectrophotometer, by Thermo Fisher Scientific (1 mentions) Phospholipid, by Avanti Polar Lipids (1 mentions) N n dimethylformamide dmf dichloromethane, by Merck Group (1 mentions)

5 protocols using 4 mercaptophenylacetic acid

Solid-Phase Peptide Synthesis with HATU

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2-chlorotrityl resin and 1-[Bis(dimethylamino)methylene]−1 H-1,2,3-triazolo[4,5-b]pyridinium-3-oxidhexafluorophosphate (HATU) were purchased from ChemPep. TentaGel R RAM resin was purchased from Rapp Polymere. Boc-Cys(Trt)-OH, Fmoc-L-Cys(Trt)-OH, Fmoc-L-Lys(Boc)-OH, Fmoc-L-Asp(tBu)-OH, Fmoc-L-Glu(tBu)-OH, Fmoc-L-Ser(tBu)-OH, Fmoc-L-Asn(Trt)-OH, Fmoc-Gly-OH, Fmoc-L-Ala-OH, Fmoc-L-Val-OH, Fmoc-L-Leu-OH, and Fmoc-Gly-Ser(psiMe,Mepro)-OH were purchased from Gyros Protein Technologies. Fmoc-Lys(Ac)-OH was purchased from Anaspec. Fmoc-Lys(Dde)-OH was purchased from AAPPTec. Synthesis grade trifluoracetic acid (TFA), ACS grade dimethylformamide (DMF), peptide synthesis grade n-methylmorpholine (NMM), synthesis grade n-methylpyrrolidinone (NMP), ACS grade anhydrous diethyl ether, HPLC grade acetonitrile (ACN), HPLC grade methanol, LC-MS grade ACN with 0.1% formic acid, and LC-MS grade water with 0.1% formic acid were purchased from Fisher Scientific (all reagent brands from Fisher Scientific were Fisher Chemical). Piperidine, triisopropylsilane (TIS), 1,2-ethanedithiol (EDT), 5 (6)-carboxyfluorescein, N,N′-Diisopropylcarbodiimide, Oxyma Pure, anhydrous hydrazine, acetic anhydride, and 4-mercaptophenylacetic acid (MPAA) were purchased from Sigma Aldrich.

Han H., Fulcher J.M., Dandey V.P., Iwasa J.H., Sundquist W.I., Kay M.S., Shen P.S, & Hill C.P. (2019). Structure of Vps4 with circular peptides and implications for translocation of two polypeptide chains by AAA+ ATPases. eLife, 8, e44071.

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Peptide Synthesis and Characterization

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Dawson (3-(Fmoc-amino)-4-aminobenzoyl) resin and HBTU were purchased from Novabiochem (San Diego, CA). 4-nitrophenylchloroformate, fluorescein-5-maleimide, Tris base and Guanidine Hydrochloride were purchased from Thermo Fisher Scientific (Waltham, MA). 4-mercaptophenylacetic acid was purchased from Sigma Aldrich (St. Louis, MO). The phospholipids were purchased from Avanti Polar Lipids (Alabaster, AL). Fmoc-(4, 4′)-Biphenylalanine (Fmoc-Bip) was purchased from Chem-Impex Int’l Inc (Wood Dale, IL). All other Fmoc-protected and Boc-protected amino acids were purchased from Advanced Chemtech (Louisville, KY) or Chem-Impex Int’l Inc (Wood Dale, IL). Peptide synthesis was carried out on a Tribute peptide synthesizer (Protein Technologies, Tuscon, AZ). Peptide concentration measurements were performed on a Nanodrop 2000c Spectrophotometer (Thermo Fisher Scientific, Waltham, MA).

Hosseini A.S., Zheng H, & Gao J. (2014). Understanding Lipid Recognition by Protein-Mimicking Cyclic Peptides. Tetrahedron, 70(42), 7632-7638.

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Solid-Phase Peptide Synthesis of Natural Compounds

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Boc-amino acids were purchased from Peptides
Institute. Boc-Leu–OCH₂–PAM resin and p-methyl-BHA (MBHA) resin were purchased from Applied Biosystems
(Foster City, CA). N,N-Dimethylformamide
(DMF), dichloromethane (DCM), N,N-diisopropylethylamine (DIEA), dimethyl sulfoxide (DMSO), methanol,
4-mercaptophenylacetic acid (MPAA), tris(2-carboxyethyl) phosphine
(TCEP), p-cresol, and HPLC grade acetonitrile were
purchased from Sigma-Aldrich (St. Louis, MO). Hydrogen fluoride (HF)
was purchased from APK (Shanghai, China). Trifluoroacetic acid (TFA)
was purchased from HaloCarbon (River Edge, NJ). Tanshinone IIA, dihydrotanshinone
1, tanshinone 1, and cryptotanshinone were purchased from Nature Standard
(Shanghai, China). Ammonium glycyrrhizinate, astragaloside A, baicalein,
curculigoside, ginsenoside Rb, ginsenoside Re, osthol, panaxadiol,
quercetin, and dihydrotanshinone were provided as generous gifts by
Dr. Sha Liao of Northwestern University of China. All natural herbal
compounds were prepared in DMSO (5–10 mM) and stored in the
dark at room temperature for no more than 1 month.

Feng C., Huang Y., He W., Cheng X., Liu H., Huang Y., Ma B., Zhang W., Liao C., Wu W., Shao Y., Xu D., Su Z, & Lu W. (2019). Tanshinones: First-in-Class Inhibitors of the Biogenesis of the Type 3 Secretion System Needle of Pseudomonas aeruginosa for Antibiotic Therapy. ACS Central Science, 5(7), 1278-1288.

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Ixonnexin Protein Synthesis and Purification

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Purified Ixonnexin (1–50) thioester 2.0 µM and Ixonnexin (51–104) 2.3 µM were dissolved in 1.9 mL of 6 M guanidine hydrochloride/200 mM PBS buffer containing 4-mercaptophenylacetic acid (Sigma-Aldrich, St.Louis, 68 mg) and tris(2-carboxyethyl)phosphine hydrochloride (TCEP, Sigma-Aldrich, St.Louis, 68 mg). The pH of the mixture was adjusted to 7.1 with 6 M sodium hydroxide and the resultant solution was kept at room temperature, monitoring ligation progress by analytical HPLC using a gradient of acetonitrile/water with UV monitoring at 215 nm. After 24 hrs the reaction mixture was acidified with diluted (~2%) TFA and the product was isolated by preparative reverse-phase HPLC and its purity checked by HPLC analyses and MALDI-TOF mass spectrometry. Pure fractions were combined, frozen, and lyophilized to afford pure unfolded Ixonnexin 1–104 with 32% theoretical yield (MALDI-TOF MS: m/z calculated 11867.1, found 11868.0 [M + H⁺]).

Assumpção T.C., Mizurini D.M., Ma D., Monteiro R.Q., Ahlstedt S., Reyes M., Kotsyfakis M., Mather T.N., Andersen J.F., Lukszo J., Ribeiro J.M, & Francischetti I.M. (2018). Ixonnexin from Tick Saliva Promotes Fibrinolysis by Interacting with Plasminogen and Tissue-Type Plasminogen Activator, and Prevents Arterial Thrombosis. Scientific Reports, 8, 4806.

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Synthesis of Gold Nanoparticles

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The following chemicals were purchased from Sigma-Aldrich Chemie GmbH, Germany, and were used as received: hydrogen tetrachloroaurate (III) trihydrate (HAuCl₄∙3H₂O), trisodium citrate dihydrate (Na₃C₆H₅O₇∙2H₂O), 11-amino-1-undecanethiol hydrochloride (AUT), 4-Mercaptophenylacetic acid (MPA) and 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES). Absolute (abs.) ethanol, hydrogen peroxide (H₂O₂), and ammonia solution 25% were purchased from Th. Geyer GmbH, Germany. All glassware was cleaned with aqua regia and rinsed with copious amounts of water prior to use. Ultrapure water with a conductivity <55 nScm⁻¹ was used for all procedures.

Nguyen V.H., Kaulen C., Simon U, & Schnakenberg U. (2017). Single Interdigital Transducer Approach for Gravimetrical SAW Sensor Applications in Liquid Environments. Sensors (Basel, Switzerland), 17(12), 2931.

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