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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/REAXYS Number:
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF4173
BCCD7896
BCCC9498
BCCB9815
BCCB1779

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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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