N methylmorpholine

Manufactured by Merck Group

Sourced in United States, Germany

N-methylmorpholine is a chemical compound used as an organic solvent and as a raw material in the production of various pharmaceutical and industrial products. It is a clear, colorless liquid with a characteristic amine-like odor. The core function of N-methylmorpholine is to serve as a versatile chemical building block and intermediate in various synthesis reactions and formulations.

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Lab products found in correlation

Piperidine, by Merck Group (10 mentions) Trifluoroacetic acid, by Merck Group (8 mentions) N n dimethylformamide (dmf), by Merck Group (8 mentions) Dichloromethane, by Merck Group (7 mentions) Trifluoroacetic acid tfa, by Merck Group (5 mentions) Dimethylformamide dmf, by Protein Technologies (4 mentions) Chlorhexidine digluconate, by Merck Group (4 mentions) Camphoroquinone, by Merck Group (4 mentions) Methacrylic acid, by Merck Group (4 mentions) 2 hydroxyethyl methacrylate, by Merck Group (4 mentions) Rink amide resin, by AAPPTec (4 mentions) Fmoc amino acid building blocks, by AAPPTec (4 mentions) 2 1h benzotriazole 1 yl 1 1 3 3 tetramethyluranium hexafluorophosphate hbtu, by AAPPTec (4 mentions) Iodoacetamide, by Merck Group (4 mentions) Methanol, by Merck Group (4 mentions) Acetic acid, by Thermo Fisher Scientific (3 mentions) Diisopropylethylamine, by Merck Group (3 mentions) 3 6 dioxa 1 8 octanedithiol dodt, by Merck Group (3 mentions) Butyl ether, by Thermo Fisher Scientific (3 mentions) 2 6 chloro 1 h benzotriazole 1 yl 1 1 3 3 tetramethylaminium hexafluorophosphate hctu, by AAPPTec (3 mentions)

Close spelling variants of this product

N-methylmorpholine (NMM) (4 citations)

48 protocols using n methylmorpholine

Solid-Phase Peptide Synthesis Protocol

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Fmoc-protected amino acids, piperidine, trifluoroacetic acid (TFA), 2-chlorotrityl chloride resin, 2 - (6 - chloro - 1H - benzotriazole - 1 - yl) - 1,1,3,3 - tetramethylaminium hexafluorophosphate (HCTU), and 1, 1-[bis(dimethylamino) methylene]-1H-1,2,3-triazolo[4,5-b] pyridinium 3-oxide hexafluorophosphate (HATU) were purchased from Advanced ChemTech (Louisville, KY). Diisopropylethylamine (DIEA), triisopropylsilane (TIPS), and N-methylmorpholine (NMM) were purchased from Sigma Aldrich (St. Louis, MO). Dimethylformamide (DMF) was purchased from Protein Technologies (Tucson, AZ). Dichloromethane (DCM), methanol (MeOH), and acetonitrile (CH₃CN) were purchased from VWR International, LLC (Radnor, PA). 4-(Fmoc-2-aminoethyl)-6-dibenzofuranpropionic acid (Fmoc-DBF) was purchased from Chem-Implex International Inc. (Wood Dale, IL).

Dahal A., Parajuli P., Singh S.S., Shrestha L., Sonju J.J., Shrestha P., Chatzistamou I, & Jois S. (2022). Targeting protein–protein interaction for immunomodulation: A sunflower trypsin inhibitor analog peptidomimetic suppresses RA progression in CIA model. Journal of pharmacological sciences, 149(3), 124-138.

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Synthesis and Characterization of Dental Composite Materials

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The following components were obtained from Sigma-Aldrich (St. Louis, MO): 2-hydroxyethyl methacrylate (HEMA), triethylene glycol dimethacrylate (TEGDMA), methacrylic acid (MA), camphoroquinone (CQ), ethyl-4-(dimethylamino) benzoate (EDMAB), diphenyliodonium hexafluorophosphate (DPIHP), mono(2-methacryloyloxy)ethyl succinate (MMES), dodecyltrichlorosilane, chlorhexidine digluconate (CHX), N,N-Dimethylformamide (DMF), dichloromethane (DCM), and N-methyl morpholine (NMM). γ-methacryloxypropyl trimethoxysilane (MPS) was used as received from MP Biomedicals (Solon, OH). Rink amide resin, Fmoc-amino acid building blocks and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluranium hexafluorophosphate (HBTU) were purchased from AAPPTec LLC (Louisville, KY). All chemicals were used as received without further purification.

Spencer P., Ye Q., Kamathewatta N.J., Woolfolk S.K., Bohaty B.S., Misra A, & Tamerler C. (2021). Chemometrics-Assisted Raman Spectroscopy Characterization of Tunable Polymer-Peptide Hybrids for Dental Tissue Repair. Frontiers in materials, 8, 681415.

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Glycoprotein Enrichment and Analysis

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Methanol (MeOH), ethanol (EtOH), acetonitrile (ACN), dichloromethane (DCM), dimethyl sulfoxide (DMSO), acetic acid (AA), formic acid (FA), and water were purchased from Fisher Scientific (Pittsburgh, PA). Formaldehyde, sodium cyanoborohydride, N-(3-(Dimethylamino)propyl)-N′-ethylcarbodiimide hydro-chloride (EDCI), N-methylmorpholine (NMM), 1-hydroxybenzotriazole hydrate (HOBt), glycine methyl ester hydro-chloride, hydrazine, triethylammonium bicarbonate buffer (TEAB, 1.0 M), and tris(2-carboxyethyl)phosphine hydro-chloride (TCEP) were purchased from Sigma-Aldrich (St. Louis, MO). PNGase F was purchased from Promega (Madison, WI). Oasis HLB 1 cc³ (30 mg) extraction cartridges were purchased from Waters Corporation (Milford, MA). Bovine thyroglobulin (BTG) was provided by Thermo Fisher Scientific (Rockford, IL). Microcon-30 kDa centrifugal filters (30K MWCO) were purchased from Merck Millipore Ltd. (Darmstadt, Germany). PolyGLYCOPLEX A beads (3 μm) were purchased from PolyLC Inc. (Columbia, MD). Fused silica capillary tubing (inner diameter 75 μm, outer diameter 375 μm) was purchased from Polymicro Technologies (Phoenix, AZ). All reagents were used without additional purification.

Feng Y., Chen B., Yu Q., Zhong X., Frost D.C., Ikonomidou C, & Li L. (2019). Isobaric Multiplex Labeling Reagents for Carbonyl-Containing Compound (SUGAR) Tags: A Probe for Quantitative Glycomic Analysis. Analytical chemistry, 91(4), 3141-3146.

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Solid-Phase Peptide Synthesis Reagents

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Fmoc-protected amino acids and synthesis resin, 2-Chlorotrityl chloride were purchased from Akaal Organics (Long Beach, CA). Dimethylformamide (DMF), N-methyl pyrrolidone (NMP), Acetonitrile and Methyl-tert. Butyl Ether (MTBE) were purchased from Fisher Bioreagents (Fair Lawn, NJ). 2-(6-Chloro-1-H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate (HCTU) was purchased from AAPPTEC (Louisville, KY). Piperidine and Dichloromethane (DCM) were from EMD-Millipore (Billerica, MA). Diisopropylethylamine (DIEA), N-Methyl-morpholine (NMM), Triisoprpopyl-silane, 3,6-dioxa-1,8-octanedithiol (DODT) and trifluoroacetic acid (TFA) were purchased from Sigma–Aldrich.

Kaseke C., Park R.J., Singh N.K., Koundakjian D., Bashirova A., Garcia Beltran W.F., Takou Mbah O.C., Ma J., Senjobe F., Urbach J.M., Nathan A., Rossin E.J., Tano-Menka R., Khatri A., Piechocka-Trocha A., Waring M.T., Birnbaum M.E., Baker B.M., Carrington M., Walker B.D, & Gaiha G.D. (2021). HLA class-I-peptide stability mediates CD8+ T cell immunodominance hierarchies and facilitates HLA-associated immune control of HIV. Cell Reports, 36(2), 109378.

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Solid-Phase Peptide Synthesis Protocol

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Fmoc-protected amino acids, 2-(6-Chloro-1H-benzotriazole-1-yl)-1,−1,3,3-tetramethylaminium hexafluorophosphate (HCTU), trifluoroacetic acid (TFA), and rink amide SS resin were purchased from Advanced ChemTech, Louisville, Kentucky. Nα-Fmoc-Nδ-allyloxycarbonyl-l-ornithine (Fmoc-Orn[Aloc]-OH) was purchased from Chem-Impex International, Inc, Wood Dale, Illinois. 1-Hydroxy-6-(trifluoromethyl)benzotriazole (HOBt) and (Ethyl cyano[hydroxyimino]acetato)-tri-(1-pyrrolidinyl)-phosphonium (PyBOP) were purchased from Novabiochem, Billerica, Massachusetts. Dimethylformamide (DMF) was purchased from Protein Technologies, Tucson, Arizona. Diisopropylethylamine (DIEA), triisopropylsilane (TIPS), tetrakis(triphenylphosphine)palladium(0) (palladium), 5(6)-carboxyfluorescein (FAM), chloroform (CHCl₃), methanol (MeOH), dichloromethane (DCM), and N-methylmorpholine (NMM) were purchased from Sigma-Aldrich, St. Louis, Missouri. Glacial acetic acid was purchased from Alfa Aesar, Ward Hill, Massachusetts. Acetic anhydride was purchased from Fisher Scientific, Fair Lawn, New Jersey.

Safa N., Anderson J.C., Vaithiyanathan M., Pettigrew J.H., Pappas G.A., Liu D., Gauthier T.J, & Melvin A.T. (2018). CPProtectides: Rapid uptake of well-folded β-hairpin peptides with enhanced resistance to intracellular degradation. Peptide science (Hoboken, N.J.), 111(2), e24092.

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Solid-Phase Peptide Synthesis Reagents

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Nathan A., Rossin E.J., Kaseke C., Park R.J., Khatri A., Koundakjian D., Urbach J.M., Singh N.K., Bashirova A., Tano-Menka R., Senjobe F., Waring M.T., Piechocka-Trocha A., Garcia-Beltran W.F., Iafrate A.J., Naranbhai V., Carrington M., Walker B.D, & Gaiha G.D. (2021). Structure-guided T cell vaccine design for SARS-CoV-2 variants and sarbecoviruses. Cell, 184(17), 4401-4413.e10.

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Peptide Synthesis via Fmoc SPPS

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Synthesis of peptide precursors was performed manually using fritted syringes on a vacuum manifold via 9‐fluorenylmethyloxycarbonyl (Fmoc) solid‐phase peptide synthesis (SPPS). All reagents were purchased from commercial sources and used without further purification. 2‐Chlorotrityl chloride resin (sub. = 1.2 mmol/g), Wang resin (sub. = 0.73 mmol/g), Oxyma Pure and all standard Fmoc amino acids were sourced from Mimotopes Pty Ltd (Australia). Fmoc‐L‐Dap(Boc)‐OH and Fmoc‐L‐Asp‐OMe were obtained from AK Scientific, Inc. (USA). Fmoc‐Cys(StBu)‐OH was sourced from CreoSalus, Inc. (USA). (1‐Cyano‐2‐ethoxy‐2‐oxoethylidenaminooxy)dimethylamino‐morpholino‐carbenium hexafluorophosphate (COMU), 1‐[bis (dimethylamino)methylene]‐1H‐1,2,3‐triazolo[4,5‐b]pyridinium‐3‐oxide hexafluorophosphate (HATU) and 2,2′‐dipyridyldisulfide (DPDS) were purchased from Combi Blocks (USA). Diisopropylcarbodiimide (DIC), 4‐dimethylaminopyridine (DMAP), diphenyldiselenide, acetoacetone, triisopropylsilane (TIPS), thioanisole, 2,2′‐(ethylenedioxy)diethanethiol (DODT), trifluoroacetic acid (TFA), piperidine, diisopropylethylamine (DIEA), N‐methylmorpholine (NMM), hydrazine hydrate, tris‐carboxyethylphosphine hydrochloride (TCEP.HCl), iodine, dimethylformamide (DMF), dichloromethane (DCM), diethyl ether, acetonitrile and trypsin were purchased from Sigma‐Merck (Australia).

Xu R., Jap E., Gubbins B., Hagemeyer C.E, & Karas J.A. (2023). Semisynthesis of A6–A11 lactam insulin. Journal of Peptide Science, 30(2), e3542.

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Synthesis and Characterization of OXA

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OXA was prepared by Laurus Labs (Hyderabad, India). 5-FU, DOCA, ethyl chloroformate, N-methylmorpholine, N^Ɛ-Boc-l-lysine methyl ester hydrochloride (H-Lys(Boc)-OMe·HCl), lithium aluminum hydride (LiAlH₄), trimethylsilyl diazomethane (2 M solution in hexane), ammonium acetate, and formic acid were purchased from Sigma-Aldrich (St Louis, MO, USA). Caprylocaproyl macrogol-8-glycerides (Labrasol), diethylene glycol monoethyl ether (Transcutol P), and propylene glycol monocaprylate (Capryol 90) were obtained from Gattefossé (St Priest, France). Polyethoxylated castor oil (Cremophor EL) was provided by BASF (Ludwigshafen, Germany). Tetrahydrofuran (THF), chloroform, methanol, acetyl chloride, and n-hexane (analytical grade) were obtained from Merck (Kenilworth, NJ, USA). Solvents for high-performance liquid chromatography (HPLC) and atomic absorption spectroscopy were obtained from Merck and Thermo Fisher Scientific (Waltham, MA, USA).

Pangeni R., Choi S.W., Jeon O.C., Byun Y, & Park J.W. (2016). Multiple nanoemulsion system for an oral combinational delivery of oxaliplatin and 5-fluorouracil: preparation and in vivo evaluation. International Journal of Nanomedicine, 11, 6379-6399.

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Synthesis and Applications of DiLeu Labels

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Synthesis of DiLeu labels required purchasing the following isotopic reagents from ISOTEC Inc (Miamisburg, OH): leucines (ʟ-leucine and ʟ-leucine-1-¹³C, ¹⁵N), heavy Formaldehyde (CD₂O, 20% w/w), sodium cyanoborodeuteride (NaBD₃CN), ¹⁸O water (H₂¹⁸O), and deuterium water (D₂O). Formaldehyde (CH₂O, 37% w/w), sodium cyanoborohydride (NaBH₃CN), trifluoroacetic acid (TFA), iodoacetamide (IAA), hydrogen chloride gas (HCl), tris hydrochloride, reagent-grade formic acid (FA), N,N-dimethylformamide (DMF), triethylammonium bicarbonate (TEAB), 4-(4, 6-dimethyoxy-1, 3, 5-triazin-2-yl)-4-methylmorpholinium tetrafluoroborate (DMTMM), sodium azide (NaN₃) and N-methylmorpholine (NMM), and dithiothreitol (DTT) were purchased from Sigma-Aldrich (St. Louis, MO). Sequencing-grade trypsin was bought from Promega (Madison, WI). Urea, ACS grade methanol (MeOH), dichloromethane (DCM, CH₂Cl₂), acetonitrile (ACN, C₂H₃N), Optima LC-MS grade ACN, water, and FA were acquired from Fisher Scientific (Pittsburgh, PA). Hydroxylamine (H₃NO, 50%) was purchased from Alfa Aesar (Ward Hill, MA).

Greer T., Hao L., Nechyporenko A., Lee S., Vezina C.M., Ricke W.A., Marker P.C., Bjorling D.E., Bushman W, & Li L. (2015). Custom 4-Plex DiLeu Isobaric Labels Enable Relative Quantification of Urinary Proteins in Men with Lower Urinary Tract Symptoms (LUTS). PLoS ONE, 10(8), e0135415.

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Solid-Phase Peptide Synthesis Protocol

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