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233412

Sigma-Aldrich

Ethyl (hydroxyimino)cyanoacetate

97%, for peptide synthesis

Synonym(s):

Ethyl cyano(hydroxyimino)acetate, Ethyl cyanoglyoxalate-2-oxime, Ethyl isonitrosocyanoacetate

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About This Item

Linear Formula:
NCC(=NOH)CO2C2H5
CAS Number:
3849-21-6
Molecular Weight:
142.11
Beilstein:
774783
EC Number:
223-351-3
MDL number:
MFCD00002112
UNSPSC Code:
12352100
PubChem Substance ID:
24853975
NACRES:
NA.22

product name

Ethyl (hydroxyimino)cyanoacetate, 97%

Quality Level

200

Assay

97%

form

solid

mp

130-132 °C (lit.)

application(s)

peptide synthesis

functional group

amine
ester
nitrile
oxime

SMILES string

CCOC(=O)C(=N\O)\C#N

InChI

1S/C5H6N2O3/c1-2-10-5(8)4(3-6)7-9/h9H,2H2,1H3/b7-4+

InChI key

LCFXLZAXGXOXAP-QPJJXVBHSA-N

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General description

Ethyl (hydroxyimino)cyanoacetate is a potential replacement for zobenzotriazole and benzotriazole derivatives used in peptide synthesis.

Ethyl (hydroxyimino)cyanoacetate is also called as Oxyma. It is a highly efficient greener alternative for the amide and peptide synthesis.

Application

Ethyl (hydroxyimino)cyanoacetate has been used as an additive for the carbodiimide-mediated amide bond formation during established peptide synthesis method.For peptide synthesis grade material, please see product 851086.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF4173
BCCD7896
BCCC9498
BCCB9815
BCCB1779

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Acta biomaterialia, 55, 183-193 (2017-04-04)
Self-assembling peptides programed by sequence design to form predefined nanostructures are useful for a variety of biomedical applications. However, assemblies of classic ionic self-complementary peptides are unstable in neutral pH, while charged peptide hydrogels have low mechanical strength. Here, we
Daniele Maiolo et al.
ChemistryOpen, 9(2), 253-260 (2020-02-29)
Here, we demonstrate that introduction of halogen atoms at the tyrosine 10 phenol ring of the DSGYEV sequence derived from the flexible amyloid-β N-terminus, promotes its self-assembly in the solid state. In particular, we report the crystal structures of two halogen-modified
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Bioconjugate chemistry, 29(9), 3026-3041 (2018-08-16)
In this study, promising approaches of dual-targeted micelles and drug-polymer conjugation were combined to enable injection of poorly soluble anticancer drugs together with site-specific drug release. Ursodeoxycholic acid (UDCA) as a hepatoprotective agent was grafted to maltodextrin (MD) via carbodiimide
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Therapeutic approaches based on nanomedicine have garnered great attention in cancer research. In vitro biological models that better mimic in vivo conditions are crucial tools to more accurately predict their therapeutic efficacy in vivo. In this work, a new 3D
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