N methylmorpholine

Manufactured by Gyros Protein Technologies

N-methylmorpholine is a chemical compound commonly used as a solvent and reagent in organic synthesis. It is a colorless liquid with a characteristic amine-like odor. The primary function of N-methylmorpholine is to serve as a versatile solvent and reagent in various chemical reactions and processes.

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3 protocols using n methylmorpholine

Peptide Synthesis and Purification Protocol

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Peptides were synthesized using a Protein Technologies SymphonyX synthesizer and using 4-methylbenzydrylamine hydrochloride resin (Iris Biotech GMBH) (Perez et al., 2018 ). Standard Fmoc-protected amino acid (AA) coupling occurred in the presence of 95 mM HCTU (Iris Biotech GMBH) and 200 mM N-methylmorpholine (Gyros Protein Technologies; S-1L-NMM) over two 20-minute coupling cycles. Fmoc deprotection occurred in the presence 20% piperidine in dimethylformamide (DMF, Iris Biotech GMBH;) over two 5-minute cycles. The peptides were purified to >95% purity by preparative C18 reverse phase HPLC (Agilent 1200 series) over a water/0.1% TFA and acetonitrile/0.1% TFA gradient characterized using HPLC-MS (Agilent 6300 MSD). Peptide substrates were dissolved in mass spectrometry grade water. Absorbance measurements at 280 nm wavelength were used to determine the peptide concentration; peptide extinction coefficients were calculated using ExPASy Bioinformatics Resource portal (https://web.expasy.org/protparam/).

Najt C.P., Khan S.A., Heden T.D., Witthuhn B.A., Perez M., Heier J.L., Mead L.E., Franklin M.P., Karanja K.K., Graham M.J., Mashek M.T., Bernlohr D.A., Parker L., Chow L.S, & Mashek D.G. (2019). Lipid droplet-derived monounsaturated fatty acids traffic via PLIN5 to allosterically activate SIRT1. Molecular cell, 77(4), 810-824.e8.

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Biotinylated PEG Peptide Synthesis

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NovaPEG Rink Amide resin and FMOC-Glu(biotinyl-PEG)-OH were purchased from NovaBiochem^®(Millipore Sigma, Billerica, MA). 2-(6-Chloro-1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate (HCTU), N,N-Dimethylmethanamide, N-Methylmorpholine, 2,2,2-Trifluoroacetic acid, and all FMOC amino acids were purchased from Gyros Protein Technologies (Tucson, AZ). FMOC-NH-(PEG)₁₁-COOH (C₄₂H₆₅NO₁₆) was purchased from Polypure (Oslo, Norway). Triisopropylsilane and 1,2-Ethanedithiol were purchased from Sigma Aldrich (Livermore, CA). Piperidine was purchased from Alfa Aesar (Tewksbury, MA), and acetonitrile, dichloromethane, diethyl ether through VWR (Radnor, PA).

Allred C.A., Gormley C., Venugopal I., Li S., McGuire M.J, & Brown K.C. (2023). Tumor-specific intracellular delivery: peptide-guided transport of a catalytic toxin. Communications Biology, 6, 60.

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Peptide Synthesis and Conjugation Protocol

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2(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate (HBTU) and the N-hydroxybenzotriazole (HOBt) were purchased from Vivitide (Gardner, MA). All protected amino acids, rink amide MBHA resin, and N-methylmorpholine (NMM) were supplied by Gyros Protein Technologies (Tucson, AZ). Polyethylene glycol (PEG₃) was obtained from Creative PEGWorks (Durham, NC). Trifluoroacetic acid (TFA), piperidine, thio anisole, anisole, 1,2-ethanedithiole, methyl-tert-butyl ether, N,N-diisopropylethylamine (DIPEA), dimethylformamide (DMF), acetonitrile (ACN), N-methyl-2-pyrrolidone (NMP), sodium carbonate, Sephadex G25, L-glutathione reduced (GSH), lipopolysaccharide (LPS), and cis-dichlorodiammine platinum (II) (cisplatin) were purchased from Sigma Aldrich (Saint-Louis, MO). Succinimidyl 3-(2-pyridyldithio)propionate (SPDP) was supplied by Invitrogen (Carlsbad, CA). p-SNC-deferoxamine (DFO) was from Macrocyclics Inc. (Plato, TX). N2’-deacetyl-N2’-(3-mercapto-1-oxopropyl)-maytansine (DM1) and aldoxorubicin HCl (aldox) were from MedKoo Biosciences (Morrisville, NC). Doxorubicin (DOX) and gemcitabine (GEM) were obtained from LC Laboratories (Woburn, MA). Mitomycin (MIT) was supplied by Selleckchem (Houston, TX). Cyanine5.5 NHS ester was purchased from Lumiprobe Corporation (Hallandale Beach, FL) and luciferin was from Caliper LifeScience (Hopkinton, MA).

Bellat V., Michel A.O., Thomas C., Stokol T., Choi B.B, & Law B. (2022). A Urinary Drug-Disposing Approach as an Alternative to Intravesical Chemotherapy for Treating Nonmuscle Invasive Bladder Cancer. Cancer Research, 82(7), 1409-1422.

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