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Ethyl cyano hydroxyimino acetate

Manufactured by Merck Group
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Sourced in United States

Ethyl cyano(hydroxyimino)acetate is a chemical compound used in laboratory settings. It serves as a key intermediate in the synthesis of various organic compounds. The core function of this product is to provide a versatile building block for further chemical transformations and reactions.

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Lab products found in correlation

N n diisopropylethylamine, by Merck Group (2 mentions) Bis boc aminooxy acetic acid, by Merck Group (2 mentions) N methyl 2 pyrrolidone, by Iris Biotech (2 mentions) Rink amide mbha resin, by Merck Group (2 mentions) N n dimethylformamide (dmf), by Merck Group (2 mentions) Triethylsilane, by Merck Group (1 mentions) 2 1h benzotriazol 1 yl 1 1 3 3 tetramethyluronium hexafluorophosphate hbtu, by Merck Group (1 mentions) Methanol, by Merck Group (1 mentions) Dichloromethane, by Merck Group (1 mentions) Triethylamine, by Merck Group (1 mentions) N n dimethylformamide (dmf), by Thermo Fisher Scientific (1 mentions) N n dimethylformamide dmf dichloromethane, by Merck Group (1 mentions) N n diisopropylcarbodiimide, by Merck Group (1 mentions) 2 1h benzotriazole 1 yl 1 1 3 3 tetramethylaminiumtetrafluoroborate, by Merck Group (1 mentions) Hplc grade acetonitrile, by Merck Group (1 mentions)

4 protocols using ethyl cyano hydroxyimino acetate

1

Solid-Phase Peptide Synthesis Protocol

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Merck Millipore (Burlington, MA, United States) provided acetic acid, acetone, acetonitrile, Fmoc-protected amino acids, Bis-Boc-aminooxy acetic acid (Aoa), dichloromethane (DCM), N,N-diisopropylethylamine (DIPEA), N,N-dimethylformamide (DMF), ethyl cyano(hydroxyimino)acetate (Oxyma Pure), methanol, Rink amide MBHA resin, triethylamine (TEA), triethylsilane (TES), and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluoro phosphate (HBTU). Biosolve (Valkenswaard, Holland) provided diethyl ether and trifluoroacetic acid (TFA). PanReac Appli-Chem (Darmstadt, Germany) provided 2-propanol for HPLC (aldehyde and ketone free), while Carlo Erba (Milan, Italy) provided ethanol. Iris Biotech GmbH (Marktredwitz, Germany) provided N-Methyl-2-pyrrolidone (NMP).
Cassari L., Zamuner A., Messina G.M., Marsotto M., Chang H.C., Coward T., Battocchio C., Iucci G., Marletta G., Di Silvio L, & Dettin M. (2023). Strategies for the Covalent Anchoring of a BMP-2-Mimetic Peptide to PEEK Surface for Bone Tissue Engineering. Materials, 16(10), 3869.
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2

Solid-Phase Peptide Synthesis Methodology

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Acetic acid, acetone, acetonitrile, Fmoc protected Amino acids, Bis-Boc-aminooxy acetic acid (Aoa), Dichloromethane (DCM), N,N-Diisopropylethylamine (DIPEA), N,N-dimethylformamide (DMF), Ethyl cyano(hydroxyimino)acetate (Oxyma Pure), Methanol, Rink-Amide MBHA resin, Triethylamine (TEA), Triethylsilane (TES), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluoro phosphate (HBTU) were purchased from Merck Millipore (Burlington, MA, USA). Diethyl ether, Trifluoroacetin acid (TFA) were purchased from Biosolve (Valkenswaard, Holland). 2-Proponal for HPLC (aldehyde and ketone free) was purchased from PanReac AppliChem (Darmstadt, Germany). Ethanol was purchased from Carlo Erba (Milan, Italy). N-Methyl-2-pyrrolidone (NMP) was purchased from Iris Biotech GmbH (Marktredwitz, Germany).
Cassari L., Zamuner A., Messina G.M., Marsotto M., Chen H., Gonnella G., Coward T., Battocchio C., Huang J., Iucci G., Marletta G., Di Silvio L, & Dettin M. (2023). Bioactive PEEK: Surface Enrichment of Vitronectin-Derived Adhesive Peptides. Biomolecules, 13(2), 246.
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3

Automated Synthesis of Cell Adhesive RGD Peptide

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A Liberty1 automated peptide synthesizer with UV monitoring (CEM) was utilized to synthesize the cell adhesive ligand CGRGDSG (RGD) on FMOC-Gly-Wang resin (EMD), as previously described (Van Hove et al., 2014 (link)). All amino acids were dissolved at 0.2 M in N,N-Dimethylformamide (DMF, Fisher Scientific). 0.5 N, N’-Diisopropylcarbodiimide (DIC) in DMF was used as an activator, and 1 M Ethyl cyano(hydroxyimino)acetate (Oxyma Pure, Sigma-Aldrich) in DMF was used as activator base. 10 wt% piperazine (Alfa Aesar) in DMF with 10 vol% ethanol was used for deprotection. The resin was then cleaved from peptides using a cleavage cocktail comprised of 92.5 vol% trifluoroacetic acid (Alfa Aesar), 2.5 vol% each triisopropylsilane (Alfa Aesar), 2.5 vol% 3,6-dioxa-1,8-octanedithiol (Alfa Aesar), 2.5 vol% ddH2O and 2.5 vol% thioanisol for 4 h. After cleavage, the resin was removed by vacuum filtration, and the resulting solution was precipitated in ice-cold diethyl ether. The peptide was collected by centrifugation and molecular weight of 655 g/mol verified using a Bruker AutoflexTM III Smartbeam Matrix-Assisted Laser Desorption Ionization Time of Flight (MALDI-ToF) mass spectrometer using α-Cyano-4-hydroxycinnamic acid as matrix.
Manian K.V., Galloway C.A., Dalvi S., Emanuel A.A., Mereness J.A., Spencer W., Winschel L., Soto C., Li Y., Song Y., DeMaria W., Kumar A., Slukvin I., Schwartz M.P., Murphy W.L., Apte B.A., Chung M., Benoit D.S, & Singh R. (2021). 3D iPSC modelling of retinal pigment epithelium-choriocapillaris complex identifies factors involved in the pathology of macular degeneration. Cell stem cell, 28(5), 846-862.e8.
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4

Peptide Synthesis Using Fmoc Chemistry

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Commercially available Fmoc-amino acids, 2-chlorotrityl chloride resin, and amino alcohols were purchased from Novabiochem, Sigma-Aldrich or Chem-Impex and used without further purification. 6-Chloro-benzotriazole-1-yloxy-tris-pyrrolidinophosphonium hexafluorophosphate (PyClocK), N,N’-diisopropylcarbodiimide (DIC), ethyl cyanohydroxyiminoacetate (Oxyma Pure), 3-[Bis(dimethylamino)methyliumyl]-3H-benzotriazol-1-oxide hexafluorophosphate (HBTU), 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate (TBTU), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridiniom 3-oxide hexafluorophosphate (HATU), 1H-1,2,3-benzotriazol-1-ol (HOBt hydrate), were purchased from Sigma-Aldrich or Chem-Impex.
N,N-dimethylformamide (DMF), dichloromethane (DCM), piperidine, trifluoroacetic acid (TFA), triisopropylsilane (TIPS), N,N-diisopropylethylamine (DIPEA), hexafluoroisopropanol (HFIP), and HPLC-grade acetonitrile were purchased from Sigma-Aldrich, Fisher, or Chem-Impex and used without further purification. All compounds are >95% by HPLC analysis with the exception of compound 16 and 19 which are >90%.
Skowron K.J., Baliga C., Johnson T., Kremiller K., Castroverde A., Dean T.T., Allen A.C., Lopez-Hernandez A.M., Aleksandrova E.V., Klepacki D., Mankin A.S., Polikanov Y, & Moore T.W. (2023). Structure-activity relationships of the antimicrobial peptide natural product apidaecin. Journal of medicinal chemistry, 66(17), 11831-11842.
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