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.
Acetic anhydride ac2o
Manufactured by Merck Group
Sourced in Italy
Acetic anhydride (Ac2O) is a clear, colorless liquid chemical compound. It is used as a reagent in various laboratory and industrial applications, primarily as a acetylating agent.
Automatically generated - may contain errors
Lab products found in correlation
N n diisopropylethylamine dipea piperidine, by Merck Group (1 mentions)
Trifluoroacetic acid tfa, by Merck Group (1 mentions)
Tris 2 carboxyethyl phosphine tcep, by Merck Group (1 mentions)
N n diisopropylcarbodiimide dic, by Iris Biotech (1 mentions)
Thioanisole, by Thermo Fisher Scientific (1 mentions)
Fmoc d phe oh, by Iris Biotech (1 mentions)
N methylmorpholine nmm, by Merck Group (1 mentions)
1 2 ethanedithiol edt, by Thermo Fisher Scientific (1 mentions)
Acetonitrile, by Scharlab (1 mentions)
Chloroform, by Avantor (1 mentions)
N n dimethylacetamide dmac, by Avantor (1 mentions)
Tmpda, by Merck Group (1 mentions)
Triethylamine tea, by Merck Group (1 mentions)
Matrimid 5218 polymer, by Huntsman (1 mentions)
Triisopropylsilane, by Merck Group (1 mentions)
Pyridine, by ITW Reagents (1 mentions)
Phenol, by ITW Reagents (1 mentions)
Isopropyl alcohol, by ITW Reagents (1 mentions)
Trifluoroacetic acid, by ITW Reagents (1 mentions)
Diethyl ether, by ITW Reagents (1 mentions)
5 protocols using acetic anhydride ac2o
1
Peptide Synthesis Using Commercial Reagents
2
Synthesis of Triazolyl-Containing MT-II Analogues
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The ω-alkynyl-alcohols
were purchased from Alfa Aesar; Fmoc-l -Trp-(Boc)-OH, Fmoc-d -Phe-OH, and Fmoc-l -Pra-OH amino acids, Fmoc-Rink
amide resin, and HOBt were purchased from Iris Biotech GmbH (Marktredwitz,
Germany); Fmoc-l -Arg(Pbf)-OH and Fmoc-l -His(Trt)-OH
amino acids were purchased from CBL (Patras, Greece); Fmoc-l -Nle was purchased from NeoMPS (Strasbourg, France); TBTU from Advanced
Biotech Italy (Milan, Italy). Peptide-synthesis grade N,N-dimethylformamide (DMF) was purchased from Scharlau
(Barcelona, Spain); acetonitrile from Carlo Erba (Milan, Italy); dichloromethane
(DCM), trifluoroacetic acid (TFA), piperidine, acetic anhydride (Ac2O), and N-methyl morpholine (NMM) were purchased
from Sigma-Aldrich (Milan, Italy). The scavengers for cleavage of
peptides from resin, 1,2-ethanedithiol (EDT), thioanisole, and phenol
(PhOH), were purchased from Acros Organics (Geel, Belgium), Jansenn
Chimica (Beerse, Belgium), and Carlo Erba (Milan, Italy).
The
purity of the final linear precursors (I′–X′)
and the [1,2,3]triazolyl-containing MT-II analogues (I–X) was
established by analytical RP-HPLC and exceeded 95%, their structural
integrity was established by ESI-MS.
were purchased from Alfa Aesar; Fmoc-
amide resin, and HOBt were purchased from Iris Biotech GmbH (Marktredwitz,
Germany); Fmoc-
amino acids were purchased from CBL (Patras, Greece); Fmoc-
Biotech Italy (Milan, Italy). Peptide-synthesis grade N,N-dimethylformamide (DMF) was purchased from Scharlau
(Barcelona, Spain); acetonitrile from Carlo Erba (Milan, Italy); dichloromethane
(DCM), trifluoroacetic acid (TFA), piperidine, acetic anhydride (Ac2O), and N-methyl morpholine (NMM) were purchased
from Sigma-Aldrich (Milan, Italy). The scavengers for cleavage of
peptides from resin, 1,2-ethanedithiol (EDT), thioanisole, and phenol
(PhOH), were purchased from Acros Organics (Geel, Belgium), Jansenn
Chimica (Beerse, Belgium), and Carlo Erba (Milan, Italy).
The
purity of the final linear precursors (I′–X′)
and the [1,2,3]triazolyl-containing MT-II analogues (I–X) was
established by analytical RP-HPLC and exceeded 95%, their structural
integrity was established by ESI-MS.
3
Fabrication of Matrimid-based Membranes
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Activated carbon (YP-50F) was purchased from Kuraray Chemical Co. (Tokyo, Japan). Matrimid® 5218 polymer was purchased from Huntsman Corporation (Conroe, TX, USA). TMPDA, ODPA, acetic anhydride (Ac2O), graphene oxide (GO, 15–20 sheets, 4–10% edge-oxidized) and triethylamine (TEA) were purchased from Sigma Aldrich (St. Louis, MO, USA). Chloroform and N,N-dimethylacetamide (DMAc) were purchased from VWR. Distilled water was synthesized in-house. All chemicals and reagents mentioned above were used as received without additional purifications.
4
Peptide Synthesis Protocol Optimized
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The following reagents, 9-fluorenylmethoxycarbonyl (Fmoc) protected aa, O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU), N,N′-dicyclohexylcarbodiimide (DDC) and 1-hydroxybenzotrazole (HOBt), were purchased from AAPPTEC (Louisville, KY, USA), ChemMatrix resin (0.60 mmol/g) from PCAS BiomMatrix Inc. (Saint-Jean-sur-Richelieu, QC, Canada), N,N-diisopropylethylamine (DIPEA), triisopropylsilane (TIS), Triton X-100, α-cyano-4-hydroxycinnamic acid (HCCA), methanol and absolute ethanol from Sigma-Aldrich (St. Louis, MO, USA), piperidine, pyridine, phenol, potassium cyanide, isopropyl alcohol (IPA), acetonitrile (ACN), N-methyl-2-pyrrolidone (NMP), trifluoroacetic acid (TFA) and diethyl ether from Panreac (Barcelona, Spain), acetic anhydride (Ac2O), ninhydrin and ethanedithiol (EDT) from Merck (Boston, MA, USA) and dichloromethane (DCM) from The Dow Chemical Company (Bogotá, Colombia).
5
Synthesis of Fluorescently Labeled Peptides
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Amino acid derivatives and piperidine were
obtained from Iris Biotech (Marktredwitz, Germany). N,N′-diisopropylcarbodiimide (DIC), 1-hydroxybenzotriazole (HOBt),
1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), hydrazine monohydrate (N2H2·H2O), triisopropylsilane (TIS),
ammonium acetate (NH4OAc), palmitic acid, 6-maleimidohexanoic
acid, acetic anhydride (Ac2O), formic acid, Fmoc-Rink Amide
MBHA resin, and 5(6)-carboxyfluorescein (5(6)-FAM) were obtained from
Merck (Budapest, Hungary). Trifluoroacetic acid (TFA), N,N-dimethylformamide (DMF), dichloromethane (DCM), diethyl ether, and
acetonitrile (AcN) were from VWR (Budapest, Hungary).
For the
biological assays, RPMI-1640, Dulbecco’s modified Eagle’s
medium (DMEM), PBS, 2 mMl -glutamine, and trypan blue were
from Lonza (Basel, Switzerland), while trypsin, nonessential amino
acids, and penicillin–streptomycin were from Gibco (Thermo
Fisher Scientific, Waltham, MA). Fetal bovine serum (FBS) was from
EuroClone (Pero, Itlay); HPMI buffer (9 mM glucose, 10 mM NaHCO3, 119 mM NaCl, 9 mM HEPES, 5 mM KCl, 0.85 mM MgCl2, 0.053 mM CaCl2, 5 mM Na2HPO4 ×
2H2O, pH = 7.4) was prepared in-house using components
obtained from Merck (Budapest, Hungary). For the AlamarBlue assay,
resazurin sodium salt (Merck) was dissolved in PBS (0.15 mg/mL, pH
7.4) and sterile-filtered. Sigma Adjuvant System (SAS) was from Merck
(Budapest, Hungary).
obtained from Iris Biotech (Marktredwitz, Germany). N,N′-diisopropylcarbodiimide (DIC), 1-hydroxybenzotriazole (HOBt),
1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), hydrazine monohydrate (N2H2·H2O), triisopropylsilane (TIS),
ammonium acetate (NH4OAc), palmitic acid, 6-maleimidohexanoic
acid, acetic anhydride (Ac2O), formic acid, Fmoc-Rink Amide
MBHA resin, and 5(6)-carboxyfluorescein (5(6)-FAM) were obtained from
Merck (Budapest, Hungary). Trifluoroacetic acid (TFA), N,N-dimethylformamide (DMF), dichloromethane (DCM), diethyl ether, and
acetonitrile (AcN) were from VWR (Budapest, Hungary).
For the
biological assays, RPMI-1640, Dulbecco’s modified Eagle’s
medium (DMEM), PBS, 2 mM
from Lonza (Basel, Switzerland), while trypsin, nonessential amino
acids, and penicillin–streptomycin were from Gibco (Thermo
Fisher Scientific, Waltham, MA). Fetal bovine serum (FBS) was from
EuroClone (Pero, Itlay); HPMI buffer (9 mM glucose, 10 mM NaHCO3, 119 mM NaCl, 9 mM HEPES, 5 mM KCl, 0.85 mM MgCl2, 0.053 mM CaCl2, 5 mM Na2HPO4 ×
2H2O, pH = 7.4) was prepared in-house using components
obtained from Merck (Budapest, Hungary). For the AlamarBlue assay,
resazurin sodium salt (Merck) was dissolved in PBS (0.15 mg/mL, pH
7.4) and sterile-filtered. Sigma Adjuvant System (SAS) was from Merck
(Budapest, Hungary).
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