Fmoc arg pbf oh

Manufactured by GL Biochem

Sourced in China

Fmoc-Arg(pbf)-OH is a protected amino acid used in peptide synthesis. It consists of the Fmoc protecting group and the arginine side chain protected by the pbf group.

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6 protocols using fmoc arg pbf oh

Peptide Synthesis and Characterization

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The conventional amino acids, Fmoc-Ala, Fmoc-Lys(Boc)-OH, Fmoc-Arg(Pbf)-OH, Fmoc-Gly, Fmoc-His(Trt)-OH, Fmoc-Leu, Fmoc-Ser(tBu)-OH, Fmoc-Thr(OtBu)-OH, Fmoc-Trp(Boc)-OH, Fmoc-Tyr(tBu)-OH, Fmoc-Asn(Trt)-OH, Fmoc-Ile-OH, Fmoc-Phe-OH, Fmoc-Cys(Trt)-OH, Fmoc-Pro-OH, were acquired from GL Biochem Ltd. (Shanghai, China). N,N′-diisopropylcarbodiimide (DIC), Oxyma pure, 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), N,N-Diisopropylethylamine, triisopropylsilane (TIS), 1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP), nonadecanoic acid (C19) were purchased from Sigma-Aldrich (Italy). Rink amide p-methylbenzhydrylamine (MBHA) resin, Fmoc-L-Lys(Mtt)-OH, piperidine, and trifluoroacetic acid (TFA) were purchased from Iris Biotech GmbH (Marktredwitz, Germany). Anhydrous solvents [N,N-dimethylformamide (DMF) and dichloromethane (DCM)], Doxo-EMCH, matrix metalloproteinase-9 (MMP-9) and dialysis tubing benzoylated, Nile Red, and Thioflavin T were purchased from Sigma-Aldrich (Milan, Italy). Silver nitrate (AgNO₃), and trisodium citrate were obtained from Sigma-Aldrich (Luzais, Saint-Quentin-Fallavier, France). Ultrapure water was produced using a Barnstead EASYpure RoDi system (Thermo Fisher Scientific, Villebon sur Yvette, France). All chemicals and reagents were of analytical grade and used as received.

Del Genio V., Falanga A., Allard-Vannier E., Hervé-Aubert K., Leone M., Bellavita R., Uzbekov R., Chourpa I, & Galdiero S. (2022). Design and Validation of Nanofibers Made of Self-Assembled Peptides to Become Multifunctional Stimuli-Sensitive Nanovectors of Anticancer Drug Doxorubicin. Pharmaceutics, 14(8), 1544.

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Synthesis and Characterization of Hydrogelator 1

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The reagents such as N, N-diisopropylethylamine (DIPEA), O-benzotriazole-N,N,N′,N′-tetramethyluronium-hexafluorophosphate (HBTU), were purchased from ACROS Organics USA. All other amino acid derivatives including Fmoc-Phe-OH, Fmoc-His(Trt)-OH, Fmoc-Asn(Trt)-OH, Fmoc-Pro-OH, Fmoc-Arg(pbf)-OH were purchased from GL Biochem (Shanghai) Ltd. The synthesis of hydrogelator 1 is based on solid phase peptide synthesis (SPPS) and has been reported previously. The crude compound that acquired from SPPS is purified by HPLC and the overall yield of the synthesis is about 80%. ¹H-NMR and LC-MS spectra are used to characterize the product.

Li J., Du X., Powell D.J., Zhou R., Shi J., He H., Feng Z, & Xu B. (2018). Down-regulating Proteolysis to Enhance Anticancer Activity of Peptide Nanofibers. Chemistry, an Asian journal, 13(22), 3464-3468.

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Solid-Phase Peptide Synthesis Protocol

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PL-Wang resin (0.4 mmole/g) was obtained from Varian, Inc. (Shropshire, UK). Fmoc-Ser(tBu)-OH, Fmoc-Met-OH, Fmoc-Leu-OH, Fmoc-Ile-OH, Fmoc-Ala-OH, Fmoc-Lys(Boc)-OH, Fmoc-Asp(OtBu)-OH, Fmoc-Asn(trt)-OH, Fmoc-Glu(OtBu)-OH, Fmoc-Phe-OH, Fmoc-Gln(trt)-OH, Fmoc-Tyr(tBu)-OH, Fmoc-Arg(pbf)-OH, N,N′-diisopropylcarbodiimide (DIC), 4-dimethylaminopyridine (DMAP) and triisopropylsilane (TIS) were obtained from GL Biochem Ltd. (Shanghai, China). Fmoc-Val-OH, Fmoc-Gly-OH, Fmoc-His(trt)-OH and N,N,N′,N′-tetramethyl-uronium-hexafluoro-phosphate (HBTU) were obtained from CS Bio Co. (Menlo Park, USA). Dimethylformamide (DMF), dichloromethane (DCM) and dimethyl sulfoxide (DMSO) were obtained from Daejung Chemicals & Metals Co., Ltd. (Siheung, Korea). Anisole, piperidine and N,N-diisopropylethylamine (DIEA) were obtained from Sigma-Aldrich (St. Louis, USA). Trifluoroacetic acid (TFA) was obtained from Yakuri Pure Chemicals Co., Ltd. (Kyoto, Japan). Ether, Anhydrous was obtained from J.T. Baker (Center Valley, USA). Zoletil® (Virbac) and Rompun® (Bayer Parma) were obtained from SMP animal medicine (Suwon, Korea). Protease inhibitor cocktail was obtained from Roche Diagnostics (IN, USA). EDTA treated BD vacutainer® was obtained from Becton, Dickinson and Company (NJ, USA). Human Aβ42 Ultrasensitive ELISA kit was obtained from Invitrogen (CA, USA).

Cho S.M., Kim H.V., Lee S., Kim H.Y., Kim W., Kim T.S., Kim D.J, & Kim Y. (2014). Correlations of amyloid-β concentrations between CSF and plasma in acute Alzheimer mouse model. Scientific Reports, 4, 6777.

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Solid-Phase Peptide Synthesis of Fmoc-protected Amino Acids

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N-Fluorenyl-9-methoxycarbonyl (Fmoc) protected amino acids (Fmoc-Trp(Boc)-OH, Fmoc-Phe-OH, Fmoc-Arg(Pbf)-OH, Fmoc-Asp(OtBu)-OH), Fmoc-Gly-OH, 2-chlorotrityl chloride resin (100–200 mesh, loading: 0.97 mmol g⁻¹, 1% DVB), N-hydroxybenzotriazole (HOBt) and o-benzotriazole-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HBTU) were purchased from GL Biochem. Ltd (Shanghai, China) and used as received. Trifluoroacetic acid (TFA) and diisopropylethylamine (DIEA) were provided by Aladdin Reagent Co. Ltd (Shanghai, China). Piperidine, N,N-dimethylformamide (DMF) and triisopropylsilane (TIS) were obtained from Sinopharm Chemical Reagent Co., Ltd (Shanghai, China) and used as received. Rhodamine B was obtained from Aladdin. Dulbecco's Modified Eagle's Medium (DMEM), fetal bovine serum (FBS), and 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetra-zoliumbromide (MTT) were provided by Invitrogen Corp. All other chemical agents were purchased from Sinopharm Chemical Reagent Co., Ltd and used without any pre-treatment.

Ding W.Q., Qin S.Y., Cheng Y.J., Ma Y.H, & Zhang A.Q. (2018). Novel oligopeptide nanoprobe for targeted cancer cell imaging. RSC Advances, 8(54), 30887-30893.

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Synthesis of Cys-Arg-Gly-Asp peptide

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Rink Amide-AM resin (0.8 mmol/g), L-amino acids protected by N-Fluorenyl-9-methoxycarbonyl (Fmoc) (Fmoc-Cys(Trt)-OH, Fmoc-Arg(Pbf)-OH, Fmoc-Gly-OH and Fmoc-Asp(OtBu)-OH), 1-hydroxybenzotriazole (HOBt) and O-benzotriazole-N,N,N′,N′-tetramethyl-uronium-hexafluoro-phosphate (HBTU) were provided by GL Biochem. Ltd. (Shanghai, China). Diisopropylethylamine (DIEA), N,N-dimethylformamide (DMF), piperidine, trifluoroacetic acid (TFA), methanol, dichloromethane (DCM), thioanisole, ethanedithiol (EDT) and anhydrous ether were obtained from Shanghai Chemical Reagent Co. (Shanghai, China). The 4-(2-hydroxyethyl)-1-piperazineethane-sulfonic acid (HEPES) buffers, hydrogen tetrachloroaurate (III) trihydrate (HAuCl₄) and Lipofectamine 2000 (Lipo2000) were provided by Sigma-Aldrich Co. LLC.

Chen S., Li J., Ma X., Liu F, & Yan G. (2021). Cationic Peptide-Modified Gold Nanostars as Efficient Delivery Platform for RNA Interference Antitumor Therapy. Polymers, 13(21), 3764.

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Solid-Phase Peptide Synthesis Protocol

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Fmoc-Gly–OH, Fmoc-Lys (Fmoc)–OH, Fmoc-Lys (Boc)–OH, Fmoc-Arg (Pbf)–OH, O-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) were purchased from GL Biochem (Shanghai) Ltd, China. Rink amide resin (200–400 mesh, loading capacity 0.34 g mmol⁻¹) was purchased from Chem-impex International, Inc (USA). The solvent used throughout the synthesis was peptide grade N,N-dimethylformamide (DMF; Merck Australia), trifluoroacetic acid (TFA), N,N-diisopropylethylamine (DIEA), dichloromethane (DCM), triisopropylsilane (TIPS), piperidine, were purchased from Sigma-Aldrich (Australia).

Jing J., Tupally K.R., Kokil G.R., Qu Z., Chen S, & Parekh H.S. (2019). Development of a hybrid peptide dendrimer micellar carrier system and its application in the reformulation of a hydrophobic therapeutic agent derived from traditional Chinese medicine. RSC Advances, 9(5), 2458-2463.

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