N n diisopropylcarbodiimide dic

Manufactured by Iris Biotech

Sourced in Germany

N,N'-diisopropylcarbodiimide (DIC) is a coupling agent commonly used in organic synthesis and biochemistry. It is a colorless liquid that facilitates the formation of amide bonds between carboxylic acids and amines.

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Diisopropylcarbodiimide (4 citations) N,N′-diisopropylcarbodiimide (3 citations) N,N’-Diisopropylcarbodiimide (DIC), trifluoroacetic acid (TFA), scavenger triisopropylsilane (TIS) (2 citations)

7 protocols using n n diisopropylcarbodiimide dic

Synthesis of Daunomycin Conjugates

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All amino acid derivatives, the Wang resin, N,N’-diisopropylcarbodiimide (DIC), and trifluoroacetic acid (TFA) were purchased from Iris Biotech GmbH (Marktredwitz, Germany). Boc-aminooxyacetic acid (Boc-Aoa-OH), 1-hydroxybenzotriazole hydrate (HOBt), 4-(dimethylamino)pyridin (DMAP), triisopropylsilane (TIS), and hydrazine hydrate were obtained from Sigma Aldrich Kft. (Budapest, Hungary). Aminooxyacetic acid, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were from TCI Europe N.V. (Zwijndrecht, Belgium), while piperidine was purchased from Molar Chemicals Kft (Budapest, Hungary). Formic acid 2,4,6-trichlorophenyl ester (For-OTcp) was prepared in our laboratory from formic acid and 2,4,6-trichlorophenol with N,N′-dicyclohexylcarbodiimide (DCC) (Sigma Aldrich Kft. Budapest, Hungary). Daunomycin hydrochloride was a kind gift from IVAX (Budapest, Hungary). All solvents used for synthesis and purification were purchased from VWR International Kft. (Debrecen, Hungary).
Solvents and salts (NH₄OAc, NH₄HCO₃) for the mass spectrometric measurements were purchased from Sigma Aldrich Kft. (Budapest, Hungary). Double distilled water was used for sample preparation.
All reagents and solvents were of analytical grade or highest available purity.

Pethő L., Mező G, & Schlosser G. (2019). Overcharging Effect in Electrospray Ionization Mass Spectra of Daunomycin-Tuftsin Bioconjugates. Molecules, 24(16), 2981.

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Peptide Synthesis Using Commercial Reagents

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All chemicals were acquired from commercial sources and used without further purification unless otherwise stated. Solvents and reagents, including acetonitrile (CH₃CN), dimethylformamide (DMF), sym-collidine, N,N-diisopropylethylamine (DIPEA), piperidine, acetic anhydride (Ac2O), trifluoroacetic acid (TFA), and Tris (2-carboxyethyl) phosphine (TCEP) were purchased from Sigma-Aldrich (Milan, Italy). Protected amino acids and coupling agents, such as 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo [4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), ethyl 2-cyano-2-(hydroxyimino)acetate (OxymaPure^®, Marktrewitz, Germany), and N-N’ diisopropylcarbodiimide (DIC) used for peptide synthesis, were acquired from IRIS Biotech GmbH.

Zannella C., Chianese A., Monti A., Giugliano R., Morone M.V., Secci F., Sanna G., Manzin A., De Filippis A., Doti N, & Galdiero M. (2023). SARS-CoV-2 Fusion Peptide Conjugated to a Tetravalent Dendrimer Selectively Inhibits Viral Infection. Pharmaceutics, 15(12), 2791.

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Solid-Phase Peptide Synthesis Protocol

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All Fmoc-protected amino acids, N,N′-diisopropylcarbodiimide (DIC) and oxyma
(ethyl cyanohydroxyiminoacetate), were purchased from Iris Biotech
GmbH (Marktredwitz, Germany). Dichloromethane (DCM), piperidine, triisopropylsilane
(TIS), and trifluoroacetic acid (TFA) were purchased from Sigma-Aldrich
(Milano, Italy). Tentagel S RAM resin was purchased from Rapp Polymere
(Tuebingen, Germany). Acetonitrile and peptide synthesis-grade N,N-dimethylformamide were purchased from Carlo Erba (Milano,
Italy).

Quagliata M., Stincarelli M.A., Papini A.M., Giannecchini S, & Rovero P. (2023). Antiviral Activity against SARS-CoV-2 of Conformationally Constrained Helical Peptides Derived from Angiotensin-Converting Enzyme 2. ACS Omega, 8(25), 22665-22672.

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Solid-Phase Peptide Synthesis and Caspase Assay

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All solvents and reagents were used as supplied. Fmoc amino acid derivatives were purchased from Novabiochem (Billerica, MA, USA). 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyluro noium hexafluorphosphate (HATU), formic acid, trifluoroacetic acid (TFA) and N,N’-diisopropylcarbodiimide (DIC) were obtained from IrisBiotech. TentaGel^® HL-NH₂ resin (0.56 mmol/g, 110 μm particle size) was purchased from RappPolymere (Tuebingen, Germany). Cyanogen bromide (3M solution in dichloromethane), 1,4-diazabicyclo[2.2.2]octane (DABCO), iodoacetic acid, triisopropylsilane (TIS), Pipes (2,2′-(Piperazine-1,4-diyl)di(ethane-1-sulfonic acid)), ethylenediaminetetraacetic acid (EDTA), DL-dithiothreitol (DTT), caspases 3 and 7 and solvents for peptide synthesis (N,N-dimethylformamide (DMF), dichloromethane (DCM), and (N-ethyldiisopropylamine (DIEA)) were obtained from Sigma Aldrich (St. Louis, MO, USA).

, & Bąchor R. (2022). Peptidyl-Resin Substrates as a Tool in the Analysis of Caspase Activity. Molecules, 27(13), 4107.

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Optimized Peptide Synthesis Protocol

Cited 1 time

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All chemicals for peptide synthesis were from commercial sources and used without further purification unless otherwise stated. Solvents, including acetonitrile (CH₃CN), dimethylformamide (DMF) were purchased from Sigma Aldrich (Milano, Italy). Acetic acid, N,N-Diisopropylethylamine (DIPEA), piperidine, and TFA were also from Sigma-Aldrich. Protected amino acids and the coupling agents OxymePure^® (ethyl 2-cyano-2-(hydroxyimino)acetate, called Oxyma Pure) and N-N′ diisopropylcarbodiimide (DIC) used for peptide synthesis were from IRIS Biotech (Marktredwitz, Germany). The peptide was prepared as previously reported [27 (link),28 (link)], with some modifications. In particular as coupling and deprotection agents we used Oxyma/DIC/DIPEA and 40% piperidine in DMF to improve the final yield and to obtain purer products. The crude material was characterized by LC–MS [29 (link)] and purified by preparative RP-HPLC using a gradient from 20% solvent B (CH₃CN, 0.1% TFA) to 80% solvent B over solvent A (H₂O, 0.1% TFA) in 20 min, monitoring the eluate at 214 nm. The purified material was collected, lyophilized, and characterized for purity and identity by LC–MS using the conditions previously reported [29 (link)].

Tarallo V., Iaccarino E., Cicatiello V., Sanna R., Ruvo M, & De Falco S. (2020). Oral Delivery of a Tetrameric Tripeptide Inhibitor of VEGFR1 Suppresses Pathological Choroid Neovascularization. International Journal of Molecular Sciences, 21(2), 410.

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Peptide Synthesis and Purification

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All amino acid derivatives, N,N'-diisopropylcarbodiimide (DIC) and Rink-amide MBHA resin were purchased from IRIS Biotech GmbH (Marktredwitz, Germany). N,Ndiisopropylethylamine (DIEA), 1.8-diazabicyclo [5.4 .0]undec-7-ene (DBU), thioanisole, 1,2ethandithiol (EDT) were FLUKA (Buchs, Switzerland), while 1-hydroxybenzotriazole (HOBt), trifluoroacetic acid (TFA) and phenol were Sigma Aldrich (Budapest, Hungary) products. Solvents for synthesis and purification were obtained from Molar Chemicals Ltd (Budapest, Hungary). Carboxyfluorescein (cf) and all other chemicals used in biological experiments were purchased from Sigma Aldrich (Hungary). Buffers were prepared with distilled water.

Szabó I., Orbán E., Schlosser G., Hudecz F, & Bánóczi Z. (2016). Cell-penetrating conjugates of pentaglutamylated methotrexate as potential anticancer drugs against resistant tumor cells. European journal of medicinal chemistry, 115.

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Synthesis of Fluorescent Peptide Conjugates

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Fmoc-protected amino acids were purchased from ORPEGEN (Heidelberg, Germany). Fmoc-D-homocysteine(Trt)-OH and Fmoc-NH-PEG(4)-OH were purchased from Iris Biotech (Marktredwitz, Germany). Peptide resins, 1-hydroxy benzotriazole (HOBt), ethanedithiol (EDT), diethyl ether, and trifluoracetic acid (TFA) were obtained from Merck (Darmstadt, Germany). N,N’-diisopropyl carbodiimide (DIC) and 2-cyano-2-(hydroxyimino) acetic acid ethyl ester (oxyma) were purchased from Iris Biotech (Marktredwitz, Germany). Dimethylformamide (DMF) and dichloromethane (DCM) were purchased from Biosolve (Valkenswaard, Netherlands), acetonitrile (ACN) was obtained from VWR (Darmstadt, Germany). O-(7-Azabenzotriazol-1-yl)-N,N,N,N-tetramethyluronium hexafluorophosphate (HATU), N,N-diisopropylethylamine (DIPEA), piperidine, and thioanisole (TA) were obtained from Sigma-Aldrich (St. Louis, USA). 6-Carboxytetramethylrhodamine (Tam) was purchased from emp biotech (Berlin, Germany).

Fischer T.F., Czerniak A.S., Weiß T., Schoeder C.T., Wolf P., Seitz O., Meiler J, & Beck-Sickinger A.G. (2021). Ligand-binding and -scavenging of the chemerin receptor GPR1. Cellular and Molecular Life Sciences, 78(17-18), 6265-6281.

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