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8.51086

Sigma-Aldrich

Oxyma Pure

Novabiochem®

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Synonym(s):
Oxyma Pure, Ethyl cyano(hydroxyimino)acetate
Empirical Formula (Hill Notation):
C5H6N2O3
CAS Number:
Molecular Weight:
142.11
MDL number:
EC Index Number:
223-351-3

Quality Level

product line

Novabiochem®

Assay

≥99.0% (HPLC)

form

crystalline powder

reaction suitability

reaction type: Coupling Reactions

manufacturer/tradename

Novabiochem®

mp

130-132 °C

application(s)

peptide synthesis

storage temp.

2-8°C

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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2334128.512128.51095
Oxyma Pure Novabiochem®

Sigma-Aldrich

8.51086

Oxyma Pure

K-Oxyma Pure Novabiochem®

Sigma-Aldrich

8.51212

K-Oxyma Pure

PyOxim Novabiochem®

Sigma-Aldrich

8.51095

PyOxim

assay

≥99.0% (HPLC)

assay

97%

assay

-

assay

≥99.0% (HPLC)

form

crystalline powder

form

solid

form

powder

form

powder

mp

130-132 °C

mp

130-132 °C (lit.)

mp

145-155 °C

mp

-

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

15-25°C

Quality Level

300

Quality Level

200

Quality Level

200

Quality Level

300

General description

Oxyma Pure (Ethyl cyano(hydroxyimino)acetate) is a non-explosive alternative to the canonical peptide coupling additive N-hydroxybenzotriazole (HOBt). When used in place of HOBt in carbodiimide-mediated peptide bond formation, it provides products in higher yields with less racemization. The combination of Oxyma Pure/diisopropylcarbodiimide (DIC) has proven to be particularly effective in microwave-assisted peptide synthesis.
The generation of toxic hydrogen cyanide (HCN) from the reaction between Oxyma Pure and DIC has been observed. Fortunately, this side reaction can be eliminated by substituting DIC for the more hindered t-butylethylcarbodiimide.

Associated Protocols and Technical Articles
Guide to Selection of Coupling Reagents

Literature references:
[1] R. Subirós-Funosas, et al. (2009) Chem. Eur. J., 15, 9394
[2] J. Collins , et al. (2014) Org . Lett ., 16, 940.
[3] A. D. McFarland (2019) Org. Process Res. Dev., 23, 2099.
[4] S. R. Manne, et al (2022) Org. Process Res. Dev., 26, 2894.

Application

Further applications of Oxyma Pure:
  • Use in the synthesis of difficult peptides.
  • As an acidic modifier to prevent aspartimide formation.

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): crystalline powder
Assay (HPLC, area%): ≥ 99.0 % (a/a)
Identity (IR): passes test
Solubility (12,5 mmol in 25 ml DMF): clearly soluble

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Generation of Hydrogen Cyanide from the Reaction of Oxyma (Ethyl Cyano(hydroxyimino)acetate) and DIC (Diisopropylcarbodiimide)
A. D. McFarland
Organic Process Research & Development, 23, 2099-2099 (2019)
Oxyma: An Efficient Additive for Peptide Synthesis to Replace the Benzotriazole-Based HOBt and HOAt with a Lower Risk of Explosion
R. Subiros-Funosas, et al.
Chemistry?A European Journal , 15, 9394-9394 (2009)
Automatic procedures for the synthesis of difficult peptides using oxyma as activating reagent: A comparative study on the use of bases and on different deprotection and agitation conditions
A. Caporale, et al.
Peptides, 102, 38-46 (2018)
tert-Butylethylcarbodiimide as an Efficient Substitute for Diisopropylcarbodiimide in Solid-Phase Peptide Synthesis: Understanding the Side Reaction of Carbodiimides with OxymaPure
S. R. Manne, et al.,
Organic Process Research & Development, 26, 2894-2894 (2022)
High-Efficiency Solid Phase Peptide Synthesis (HE-SPPS)
J. Collins , et al.
Organic Letters, 16, 940-940 (2014)

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