Wang resin

Manufactured by Merck Group

Sourced in United States, Germany

Wang resin is a type of solid-phase resin used in organic synthesis. It is a polystyrene-based resin that is functionalized with a hydroxybenzotriazole group, which allows for the attachment of amino acids or other molecules during peptide synthesis or other chemical reactions. The core function of Wang resin is to provide a solid support for the immobilization of these molecules, enabling their subsequent chemical manipulation and purification.

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Preloaded Fmoc-protected Wang resin (2 citations)

5 protocols using wang resin

Synthesis and Characterization of Functionalized Boltorn H40

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Boltorn H40 (Sigma-Aldrich) was purified by precipitation from acetone and diethyl ether and dried under a vacuum at room temperature before use. Amino acids, coupling agents and the Wang resin (0.87 mmol/g) were obtained from EMD Millipore USA and used as received. The Rink amide resin (Rink amide chemMatrix, 0.49 mmol/g) was purchased from Biotage. Fmoc–N–amido–dPEG₄–acid (Quantabiode-sign), mannosamine hydrochloride (Aldrich), triethylamine (TEA, Aldrich), dimethylamino pyridine (Aldrich), azido-dPEG₁₂–NHS ester (Quanta Biodesign), pHRodo red succinimidyl ester (Thermofisher), O-(2-azidoethyl)-O′-methyl-triethylene glycol (Aldrich), 1,2-ethanedithiol (EDT, Al-drich), phenol (Acros Organics), diisopropylethylamine (DIPEA, Aldrich), trifluoroacetic acid (TFA, Alfa Aesar), thioanisole (Aldrich), triisopropylsilane (TIPS, Aldrich), succinic anhydride (Acros Organics), N-(3-(dimethylamino)-propyl)-N′-ethylcarbodiimide hydrochloride, EDC·HCl (Al-drich), N-hydroxybenzotriazole (HOBT, Aldrich) and dibenzylcylooctyne (Click Chemistry Tools) were used as received. Methanol (Fisher) and dimethylformamide (Fisher) were dried over molecular sieves (Aldrich) of 3 and 4 Å, respectively. Azidovaleric acid was synthesized in accordance with a previously published protocol.⁷⁰ All other solvents were purchased from Fisher at the highest purity available and used as received.

Kakwere H., Ingham E.S., Allen R., Mahakian L.M., Tam S.M., Zhang H., Silvestrini M.T., Lewis J.S, & Ferrara K.W. (2017). Toward Personalized Peptide-Based Cancer Nanovaccines: A Facile and Versatile Synthetic Approach. Bioconjugate chemistry, 28(11), 2756-2771.

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Synthesis and Characterization of Antimicrobial Peptides

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In our experiment, we used two peptides LL-37 (LLGDFFRKSKEKIGKEFKRIVQRIKDFLRNLV-PRTES) and KR-12 (KRIVQRIKDFLR) which were synthesized manually by solid-phase method using 9-fluorenylmethoxycarbonyl (Fmoc) chemistry on a Wang resin (loading 0.50—mmol/g, 100–200 mesh, Merck, Germany) according to procedures described in our previous works [12 (link), 13 (link)]. The purity of peptides after purification was at least 95%, as determined by analytical reversed-phase high-performance liquid chromatography (RP HPLC). Their identity was confirmed by the matrix-assisted laser desortion/ionization time-of-flight (MALDI TOF) mass spectrometry. All drugs were dissolved in 5% dimethyl sulfoxide (DMSO) in saline, which was used as vehicle.

Fabisiak N., Fabisiak A., Chmielowiec-Korzeniowska A., Tymczyna L., Kamysz W., Kordek R., Bauer M., Kamysz E, & Fichna J. (2020). Anti-inflammatory and antibacterial effects of human cathelicidin active fragment KR-12 in the mouse models of colitis: a novel potential therapy of inflammatory bowel diseases. Pharmacological Reports, 73(1), 163-171.

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Solid-phase Peptide Synthesis Protocol

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The peptides were synthesized by solid phase methods using reagent systems and methodologies of standard Fmoc-chemistry 36 (link),37 (link). Fmoc-L-Asp-(OtBu)-OH, Wang resin, diisopropylethylamine (DIPEA), trifluoroacetic acid (TFA) and triisopropylsilane (TIS) were purchased from Sigma-Aldrich. All other Fmoc-protected amino acids (Fmoc-L-AA-OH) were prepared from the corresponding α-amino acids and 9-fluorenylmethyloxycarbonyl chloride 38 (link). O-Benzotriazole-N,N,N′,N′-tetramethyl-uronium-hexafluoro-phosphate (HBTU) was purchased from Matrix Innovation.
For the synthesis of polyethylene glycol (PEG)-attached peptide was used TentaGel® PAP Resin (Rapp Polymere GmbH, Tuebingen, Germany), a polystyrene/DVB matrix with amine terminated polyethylene oxide attached via a cleavable linkage with TFA. Dichloromethane (DCM), N,N-dimethylformamide (DMF), N-methylpyrrolidone (NMP), diethyl ether, formic acid (FA), HPLC grade water and acetonitrile were obtained by VWR.
The peptides were characterized by NMR spectroscopy and LC/MS analysis. Electrospray ionization source-quadrupole time of flight (ESI-QTOF) mass spectra and ¹H NMR and ¹³C NMR spectra identified correct and pure samples (more details in Data S1).

Catalano S., Leggio A., Barone I., De Marco R., Gelsomino L., Campana A., Malivindi R., Panza S., Giordano C., Liguori A., Bonofiglio D., Liguori A, & Andò S. (2015). A novel leptin antagonist peptide inhibits breast cancer growth in vitro and in vivo. Journal of Cellular and Molecular Medicine, 19(5), 1122-1132.

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Fmoc Solid-Phase Peptide Synthesis

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Peptides were synthesized by standard Fmoc solid-phase synthesis. The first Fmoc-amino acid was loaded on Wang resin (Sigma-Aldrich) by esterification with N,N′-Dicyclohexylcarbodiimide/4-dimethylaminopyridine. The peptide chains were elongated by using Fmoc-amino acids (3 eq.), N,N-diisopropylethylamine (DIPEA, 6 eq.), HBTU (3 eq.), and HOBt (3 eq.) in N-methylpyrrolidone (NMP) for coupling and 20% piperidine in NMP for Fmoc deprotection. All peptides were cleaved from the resin and deprotected by treating with trifluoroacetic acid (TFA)/triisopropylsilane/water (95:2.5:2.5 v/v). Crude peptides were precipitated in cold diethyl ether and purified by semi-preparative RP-HPLC running a linear gradient of acetonitrile at a flow rate of 3.0 mL min^–1 on a COSMOSIL 5C18-AR-300 or 5C18-AR-II packed column (10 × 250 mm) with ultraviolet detection at 220 nm. We used eluent A (0.1% TFA ultra-pure water) and eluent B (0.08% TFA acetonitrile). Pure fractions were analyzed by analytical RP-HPLC and MALDI-TOF MS. The pure peptides were lyophilized.

Miki T., Nakai T., Hashimoto M., Kajiwara K., Tsutsumi H, & Mihara H. (2021). Intracellular artificial supramolecules based on de novo designed Y15 peptides. Nature Communications, 12, 3412.

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Synthesis and Purification of PNC-28 Peptide

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In the synthesis of PNC-28 Peptide the reagents used are obtained from Sigma-Aldrich Company and these are Wang Resin, Fmoc protected amino acids (ETFSDLWKLL), additives (HOBT and HBTU, HATU and HOAT), Diisopropylcarbodiimide, DMF, DCM, IPA, IPE, TFA, DI water, KCN, Pyridine, n-Butanol, Ninhydrin, Phenol, trifluoroacetic acid (82.5% v/v), Phenol (5% v/v), water (5% v/v), thioanisole (5% v/v), 1,2-ethanedithiol (2.5% v/v), Diethyl ether. The equipment used is also obtained from Sigma-Aldrich Company and they are frit glass vessel, caframo, stopper test-tubes, weighing machine, round bottom flask, desiccator, lyophilizer.

Verma D., & Rajasekharan P.V.N. (2020). Synthesis and Characterization of Kalata B2 Cyclotide (GLPVCGETCFGGTCNTPGCSCTWPICTRD) on Wang Resin, as Solid Support. Open Journal of Medicinal Chemistry, 10(02), 46-55.

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